Affordable Stays Near Ashmere Lake, MA: Hotels & More

Autumn Hill Lakehouse
House
Hinsdale, MA, USA

19 miles from Cranwell Spa & Golf Club in Hinsdale, Autumn Hill Lakehouse features accommodations with access to spa facilities. The vacation home has access to a restaurant. The vacation home has a children's playground and a hot tub. Providing access to a balcony, the vacation home consists of 3 bedrooms. Featuring a terrace, this vacation home also comes with a flat-screen TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 3 bathrooms with a hot tub and free toiletries. The property has an outdoor dining area. Guests at the vacation home will be able to enjoy activities in and around Hinsdale, like cycling. Guests can also warm up near the outdoor fireplace after a day of skiing. Tanglewood Musical Center is 19 miles from Autumn Hill Lakehouse, while Tanglewood is 19 miles from the property. Bradley International Airport is 53 miles away.

Amenities:

Balcony/Terrace • Child Friendly • Hot Tub • Wellness Facilities • Fireplace/Heating • Spa • Barbecue/Outdoor Cooking • Guest Services • Skiing • Security/Safety • Laundry • Restaurant

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Apartment
Dalton, Massachusetts, USA

Just bring your clothes and food! Everything else is here. Everything to cook with clean, shower, extra linens and blankets. Nice front and back porches.

Plenty of parking. Centrally located in the beautiful Berkshires, a short drive to anything. The stairs are very quirky and not for the faint at heart. You'll love them or hate them! See picture.

***NOTE: We are family-friendly! We make an extra effort to ensure that children and pets feel welcome and are comfortable. No breed or size limits for dogs!

180-year-old home with plenty of modern updates to make anyone feel at home.

2 bedrooms , one with a king bed and the other with a trundle with 2 twin beds. There is a Queen air mattress, able to be set up in any room guests choose. Pack and Play with sheets and blankets is also always available and can be used in any room. Extra sheets, blankets, and pillows are always available.

There is other equipment for traveling babies and toddlers, such as an infant swing, boppy, Bumbo seat, wagon, and toys. A stroller can be provided with advance notice.

The modern bathroom features a large walk-in shower and a hair dryer for convenience.

WiFi and smart TVs make your downtime relaxing. Alexa in the kitchen can be moved to any room you choose.

Modern washer and dryer is available for use at any time at no charge.

Experience what the Berkshires has to offer in this centrally located home in the friendly and safe town of Dalton! While visiting, don't forget to stop at Waconah Falls, The Pines, and Holiday Brook Farm!

Guest Reviews:

- "The property was very clean, easy to access and amazing with all the extras that most places don’t include. The water was really hot and it never ran out. The bed was out of this world comfortable. Property owner was very responsive and more than willing to help. Dogs welcome. I would definitely recommend this property. I hope to return sometime in the near future " - "This is an incredibly well renovated and extraordinarily comfortable house - one might never guess given the age of the property! It has been very tastefully decorated, and the thoughtfulness of the owner/operator is eminently evident. With the many (over 15) wonderful experiences I have had in recent year at VRBOs this one still stands out due to the extremely well stocked nature of the house in general, and the kitchen in particular! Additionally we were permitted to park a car in the abundantly large parking space outside of our reservation hours which made a HUGE difference in the convenience afforded to our point to point hiking the Appalachian Trail in the Cheshires. All of us who stayed would wholeheartedly recommend this as THE place to stay if hiking the Appalachian Trail in Massachusetts or theCheshires! "

Picturesque Cottage with Sunroom on Ashmere Lake!
House
Hinsdale, MA, USA

Picturesque Cottage with Sunroom on Ashmere Lake! is located in Hinsdale, just 18 miles from Cranwell Spa & Golf Club and 18 miles from Tanglewood Musical Center. This vacation home provides air-conditioned accommodations with a patio and free Wifi. The Clark Art Institute is 29 miles from the vacation home. The vacation home features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a hair dryer. Towels and bed linen are provided in the vacation home. The property has an outdoor dining area. Tanglewood is 18 miles from Picturesque Cottage with Sunroom on Ashmere Lake!, while Norman Rockwell Museum is 24 miles away. Bradley International Airport is 53 miles from the property.

Amenities:

View • Sports/Activities • Oceanfront • Private Beach • Security/Safety • Fireplace/Heating • Ocean View • Guest Services • Internet • Other • Parking

Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!
House
Hinsdale, Massachusetts, USA

Treat your family to the ultimate getaway in the Berkshires at this beautiful vacation rental on Lake Ashmere! The 3-bedroom, 4.5-bath home has ample amenities to keep everyone entertained, including a canoe, 2 kayaks, a fire pit, a ping-pong table, and 2 Smart TVs. Enjoy a relaxing afternoon on the water, or drive around and visit top attractions — Tanglewood is 19 miles away, and MASS MoCA is 21 miles away! In the evening, share dinner on the deck and admire the incredible sunset view.

-- THE PROPERTY --

C0495241320 | Ping-Pong Table | Canoe & 2 Kayaks | Sunset View

Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: 2 Twin XL Beds | Upstairs Living Room: Full Sleeper Sofa

OUTDOOR LIVING: Private dock (no boats) w/ lake access, deck, patio, dining area, electric grill, fire pit (starter wood provided), private yard
INDOOR LIVING: Smart TVs, dining table, board games, laptop-friendly workspace
KITCHEN: Stove/oven, refrigerator, microwave, cooking basics, dishware & flatware, Keurig & coffee pods, blender, toaster, spices, trash bags & paper towels
GENERAL: Free WiFi, mini-split A/C & heating, complimentary toiletries, linens & towels, in-home laundry, laundry detergent, life vests, hair dryer, hangers
FAQ: Doorbell camera (facing front entry), quiet hours (10:00 PM-8:00 AM)
ACCESSIBILITY: 3-story home, 4 steps for entry, bedroom & 1.5 bathrooms on main level
PARKING: Driveway (3 vehicles), across the street (1 vehicle), no street parking

-- THE LOCATION --

OUTDOOR ACTIVITIES: Ashmere Lake (on-site access), Ashmere Lake State Park (1 mile), Wahconah Falls State Park (6 miles)
WINTER FUN: Bousquet Mountain Ski Area (15 miles), Jiminy Peak Mountain Resort (20 miles), Berkshire East Mountain Resort (23 miles), Butternut Ski Area and Tubing Center (32 miles)
AREA ATTRACTIONS: Berkshire Theatre Group (11 miles), Shakespeare & Company (18 miles), Tanglewood (19 miles), MASS MoCA (21 miles), Jacob's Pillow (22 miles), Norman Rockwell Museum (24 miles), Clark Art Institute (28 miles)
AIRPORT: Albany International Airport (57 miles)

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: This 3-story home requires 4 steps for entry. While there is a bedroom and 1.5 bathrooms on the main floor, interior stairs are required to access the lower-level bathroom and the upper-level bedrooms and bathrooms
- NOTE: Your safety matters. This property features a doorbell camera on the front door facing the exterior entry. The camera does not look into any interior spaces. The camera actively records video and sound when motion is detected
- NOTE: Please observe quiet hours from 10:00 PM to 8:00 AM
- NOTE: Boats are not allowed on the private dock

Amenities:

Air Conditioner • Fireplace/Heating • Laundry • Security/Safety • Sports/Activities • Barbecue/Outdoor Cooking • Bedding/Linens • Internet • Kitchen • Entertainment • Wellness Facilities • Balcony/Terrace

Pittsfield Home with Deck - 12 Mi to Jiminy Peak!
House
Pittsfield, MA, USA

Pittsfield Home with Deck - 12 Mi to Jiminy Peak! is located in Pittsfield, just 12 miles from Tanglewood Musical Center and 12 miles from Tanglewood. This vacation home offers accommodations with a balcony. Free Wifi is available throughout the property and Cranwell Spa & Golf Club is 12 miles away. The vacation home consists of 3 bedrooms, 2 living rooms, a fully equipped kitchen with a dishwasher and a coffee machine, and 3 bathrooms with a bath and a hair dryer. Towels and bed linen are offered in the vacation home. The accommodation has a fireplace. Norman Rockwell Museum is 17 miles from the vacation home, while The Clark Art Institute is 20 miles from the property. Albany International Airport is 45 miles away.

Amenities:

Internet • Fireplace/Heating • Parking • Child Friendly • Other • Sports/Activities • Accessibility • Security/Safety • Guest Services

Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences
House
Peru, Massachusetts, USA

Swiss chalet type house with exposed douglas fir beams. Back of home has all windows opening to deck and forest. 2 bedrooms with open loft for 3rd bedroom, with 2 baths. Sleeps 6 people but open to a larger group. Has modern appliances including sub zero refrigerator, dishwasher, washer/dryer, high speed internet with television. Open kitchen, great for entertaining with large table that seats 20. Glass enclosed shower downstairs with tub/hand shower upstairs. Quiet forest surrounding with some trails and country roads for walking. Near all of Berkshire lakes, trails, arts and country life. 20 minutes from all shopping.

Guest Reviews:

- "We enjoyed our stay very much. The house was clean and well maintained. It had all the amenities one would want. The location was great... right in the middle of a forest with the comforts of home." - "The house is quite large and with all amenities you would have home. The location is inside a state forest, with absolute quiet and crispy clean air . As remote as it sounds, it's only 20 minutes from Pittsfield, with a large mall including two supermarkets , Walmart, Home Depot, Starbucks and many more. I highly recommend Patrick's Pub , great food and beer with reasonable prices. If you don't mind driving a beat more through a beautiful scenery and go to Great Barrington, you can find great local restaurants and our favorite pizza Baba Louie's. Otherwise the host has thought of everything, house is stacked with the necessary toiletries/paper products, and much more."

Lakefront Hinsdale Home about 10 Mi to Pittsfield!
House
Hinsdale, MA, USA

Lakefront Hinsdale Home about 10 Mi to Pittsfield! is located in Hinsdale, just 18 miles from Tanglewood and 23 miles from Norman Rockwell Museum. The air-conditioned accommodation is 18 miles from Tanglewood Musical Center. Free Wifi is available throughout the property and Cranwell Spa & Golf Club is 18 miles away. Featuring a patio and lake views, the spacious vacation home includes 3 bedrooms, 2 living rooms, cable flat-screen TV, an equipped kitchen, and 5 bathrooms with a bath and a shower. Towels and bed linen are offered in the vacation home. The property has an outdoor dining area. The Clark Art Institute is 29 miles from the vacation home.

Amenities:

Guest Services • Child Friendly • Internet • Accessibility • Security/Safety • Other • Sports/Activities • Fireplace/Heating • Parking

Remote and Relaxing Cabin in the Berkshires
House
Peru, Massachusetts, USA

Wake up to a beautiful view from this A-frame home built by our family. Unpack and unwind! Spend the day hiking(or snow shoeing) the property(60 acres), go into town for a great meal and entertainment and finish the day by the firepit roasting s'mores. The sunset is absolutely breathtaking (visible from inside or outside). This house is our retreat and we invite you to enjoy the calmness of the area and to Slow Down. Unplug in the Berkshires as we so enjoy doing. Tons of activities in every season to enjoy in the Berkshires!
Close to various attractions: Museums, Ski resorts(Bosquet, Jiminy Peak, etc), Notchview
For Cross Country skiing or snow shoeing, Ashmere Lake for kayaking, countless parks/reserves, Farmers Markets, Wineries, Breweries, Orchards, Shopping, Concert Venues, etc all within a short drive.
We have two pairs of adult snow shoes and a sled to share! Ping pong table and corn hole too!
Pots, pans, knives, cutlery, slow cooker, Panini maker, toaster, Keurig and Dutch oven included. Wood is supplied for the firepit, as well as adirondack chairs to sit. A gas grill is on the deck, and propane is provided. Games and puzzles are also available for your use.
Linens(sheets, towels and blankets) included in each bedroom as well. Laundry and cleaning included.
4 WD VEHICLE highly recommended during winter & rainy seasons!
NO PETS ALLOWED.

Guest Reviews:

- "The cabin was exactly as described, and very clean and comfortable. We really enjoyed our stay!" - "Our family had a wedding in nearby Worthington and needed a place for 8. House was great, plenty of space and equipped well for us to cook and relax in between the various events. Nice view and very relaxing, quiet spot." - "The property is 100% as advertised. If anything, their underselling the property. Communication with the owner was well above average. Our whole party loved the home and had a great time."

Bershire Home Rental: Enjoy Berkshire Fall Foliage
House
Washington, Massachusetts, USA

Beautiful house in rural northern Berkshire County. Property sits on 8 acres of land, 4 acres mowed and maintained. Two 1200 square foot barns. In ground swimming pool. 4 bedrooms, 1 bath. Fenced in area for pets. Fully furnished. There is a finished bedroom in the downstairs that can serve as additional living space or game room. 20 minutes from the New York State line and 30 minutes from Bennington, Vermont. Great for summer events - close to Lee, Stockbridge, Tanglewood. Excellent for winter skiing, snowmobiling. Wonderful for fall foliage. Hunting for all seasons. Abundance of state parks including October Mountain. Close to skiing areas including Jiminy Peak, Catamount and Butternut. Close to snow mobile trails, cross country skiing, hiking.

Internet and WiFi, DishNet for TV (TVs in all rooms - 5 total). Great place for weekly or monthly rental. Pets are allowed. Heat sources include wood (wood stove in main living area), oil, and electric. Front porch and back deck. Large pool area - pool has diving board and is 12 feet deep at one end and 3 feet deep at the other.

Guest Reviews:

- "We a family of 6 had a great time staying at this property. There's 2 bedrooms upstairs and 2 in the basement, so its plenty of space for everyone to spread out. We loved how open the house was, no clutters, and as a family with a 2 year old that was very appreciated. The kitchen was well stocked with all kind of appliances, dinnerware, and an array of condiments. Kids had a blast in the pool. You are in a good location to explore town and adjacent ones. Thank yoi for providing a clean and safe home to guests."

Quiet Lake house with beautiful water views
House
Hinsdale, Massachusetts, USA

Massachusetts lake house on beautiful Ashmere lake in the Berkshires. Living room and porch provide beautiful views of the lake. House is situated with direct view and access to lake and boat dock. Recently finished complete interior remodeling including new kitchen, bedrooms, wood floor. House includes association access to boat docks and 5 minute walk to beach with picnic area/ playground. Rental includes use of row boat and paddle boat. Broadband internet with WiFi now available. Recent update includes Mini-splits which provide A/C in summer and heat in warm months.

Guest Reviews:

- "My family and I stayed here for some quiet family bonding time. The property was right near the lake. We enjoyed the peddle boat/paddle board. Played a lot of cards and games. Beautiful spot with shops close by if you forget anything, Peaceful and quiet. Would definitely come back for another visit." - "We had a fantastic time, even though the rain kept us indoors. The host provides lots of games and cards to play! Very well stocked with everything you need!"

Berkshire Lake access
House
Hinsdale, Massachusetts, USA

Our beautiful offshore lake house is walking distance to a private HOA beach. Bring friends or family to our four bedroom two bath house with a large open living/kitchen area and a quiet sun room where you can read and watch the birds. Or have cocktails.

Cook a family meal in the well appointed kitchen. There are extra table leafs in the closet to add space for your guests. Enjoy! Your on vacation.

This house can be rented for multi month periods for a greatly reduced price. Contact owner for info.

Guest Reviews:

- "Absolutely stunning home! Everything and anything you need is there! Just bring your clothes and food. Plenty of trails to hike. Joni is a pleasure to talk with and quick to respond to your needs. Thank you" - "It is like you are camping but in a house. It is so spacious that my parents came this year with the kids and my husband. It is a 20 sec walk to the lake. This year we took advantage of the kayaks. My 9 yr son loved it!" - "My husband and I stayed with our adult daughters and their spouses and there was plenty of room. It's a very comfortable home with 4 bedrooms. It is right across the street from a very pretty lake with a small beach which we were lucky enough to have to ourselves. There were also kayaks for our use which we used several times. The house is also just about 15 minutes away from a beautiful waterfall you can see with a very quick hike."

Ashmere Lake Log Cabin with privacy/2 Bedrooms/3 night minimum
Cabin
Hinsdale, Massachusetts, USA

Brand new log cabin. Charming, quiet with privacy. If peace and tranquility are one of your vacation objectives, then this is the home for you! Enjoy cooking on the grill while having an evening cocktail while the kids take advantage of the board games which are provided. You can enjoy a dip in the lake with access to the private, shared beach.
With the fall foliage season upon us,come and enjoy a family visit to the Mohawk Trail,with whitewater rafting on the Deerfield River, Pleasant Valley Wildlife Sanctuary, Cricket Creek Farm in Williamstown, Wine tasting at Hilltop Orchards, Berkshire Botanical Gardens in Stockbridge, Catamount Aerial Adventure Park and Adventures at Bousquet Mountain. History abounds with trips to Chesterwood, Arrowhead, Wiliams College Museum of Art, Clark Art Institute and Susan B. Anthony Birthplace Museum in Adams, Mass Moca.
For the little ones, don't forget to visit Ioka Valley Farm and Whitney's Farm for many activities including the Petting Zoo, Dairy Bar, u-pick pumpkins, corn maze, hay rides, Giant slide, Jumpin' Pumpkin and the Scavenger Hunt.
Also, for the teenagers and adults try your skills at Ramblewild in Lanesboro and take a drive up to Mount Greylock ( highest peak in Massachusetts ) to view the spectacular colors while having lunch or dinner at the newly opened restaurant.

Specials on extended stays are available. Just ask.

Guest Reviews:

- "Very peaceful place, charming cabin, very comfortable" - "Very happy with the cabin. Nice area and location was easy to get to." - "This was a beautiful super clean cabin. Marlene was a fabulous host and very kindly greeted us. We definitely will stay there again if we end up back in that area." - "My husband and I spent a long weekend at the cabin to celebrate our anniversary. It was perfect. The cabin was absolutely beautiful, spotlessly clean and located in a peaceful location. Loved it!"

Brooksong, the perfect Berkshires getaway
House
Dalton, Massachusetts, USA

*All bookings are subject to COVID-19 regulations by the state of Massachusetts.

*Until regulations change, all guests coming from out-of-state are asked to observe a 14-day self-quarantine while at Brooksong. Please contact for more information.

*Cleaning staff is working double to sanitize as thoroughly as possible. I also try to block off at least 2 days between each booking for safety reasons.

Located in the lovely Berkshire mountains, part of this bright, sprawling property was built in 1866 as a schoolhouse. It has since retained its historic charm while including all the updated comforts of home. Play pool, sip cocktails at the antique 1920s bar, sing songs around the outdoor fire pit, cook dinner in the huge kitchen or enjoy grilling on the porch in the sun. Skiers and hikers will love the area, and with over five acres of wooded land to explore, the property is perfect for a vacation with friends or family reunion.

Brooksong is an incredibly unique space, full of historical flourishes and quirks, and the house has been entirely renovated with comfort in mind. Lovingly maintained, Brooksong has the ideal combination of classic and modern decor. The house comfortably sleeps ten so you can enjoy a great weekend in the Berkshire countryside with the people you care about.

In addition to Brooksong's five acres of land, the Berkshires have many other beautiful woods and meadows to hike in. Wahconah Falls State Park is just up the road, and the dramatic waterfall is definitely worth checking out. Skiers should note that there are several places nearby to hit the slopes; the closest, Jiminy Peak, is about 25 minutes away. For some culture, the Massachusetts Museum of Contemporary Art is a half hour's drive from the house. The town of Dalton has some quaint restaurants and shops, and the Berkshires are renowned for their array of adorable villages and hamlets to browse. The town of Pittsfield is about 10 minutes away, and has all the strip mall options you could ask for: Stop & Shop, Home Depot, Target, etc. In other words, you'll be secluded but not cut off from civilization! Holiday Farms is a great organic farm just up the road and there are many similar establishments nearby, so I highly recommend trying some local meat, dairy and produce.

*The following would not usually be included here, but we live in strange times. Brooksong has few neighbors and they are separated from the property by farmland and woods. Our water comes from a well. Self-sustaining farms are within walking distance. The nearest hospital is BMC, about 12 minutes away by car, and there are many places nearby still open to get supplies, as well as grocery delivery in the area. The WiFi is excellent and all the infrastructure necessities of the house, like propane, are constantly maintained. My house manager is on call 24/7 for any problems. Honestly, there are few better places to get away from crowded areas and ride out the current situation than Brooksong. We will do our best to make sure you feel safe and comfortable during this stressful time.

Guest Reviews:

- "Super clean and beautifully laid out and decorated " - "Had fun here for a guys weekend trip. Good location and fun comfortable house." - "This house was just excellent, from check-in to check-out. Communication with Sulmone was great. The property is private with farms surrounding the property, a great all-around place for a large family or families to stay. The drawers and cabinets were well stocked with all the utensils, pots, and pans you will need for cooking and eating in. The beds and linens were very comfortable and made sleeping easy. We stay at many VRBOs and I have to say this one was one of the top places yet. The radiant floor heating warmed the house up to take the chill out, unlike forced hot air to dry the air out. The yard has a nice fire pit with no worries. Bottom line you need to make an effort to stay at this house to really enjoy it and experience a great relaxing property. Stores are close enough if you forget something or need to pick up groceries. 5 Stars out of 5 for sure!"

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Cabin
Hinsdale, Massachusetts, USA

Welcome to Lake Ashmere!

Our newly and completely renovated cottage features two bedrooms with comfy queen size beds, a loft with two full size beds, cathedral ceilings, year-round six person hot tub and a large working kitchen stocked with everything you need. The living space is bright and airy. WiFi in the cottage is over 500 mbps, making it ideal for longer stays.

Set in a peaceful location, the cottage is just a three minute walk to Lake Ashmere where you can relax and enjoy the lake. During the winter time, the lake freezes over and makes for a great view.

The cottage is also perfectly situated for your winter adventures. Nestled in the heart of the Berkshires, our home is a cozy retreat just 25 minutes from Jiminy Peak Ski Mountain and Bousquet Mountain, and within an hour of premier slopes like Mount Snow (1 hr 15 min), Berkshire East Mountain (35 min), and Butternut (45 min).

After a day of skiing, snowboarding, or tubing, unwind in the warm ambiance of the cottage, complete with modern amenities and plenty of space to relax. Soak your cares away in our private 6-person hot tub, the perfect way to ease tired muscles and enjoy the crisp winter air under the stars.

The Berkshires isn’t just for skiing—there’s so much more to enjoy during the winter:

Family-Friendly Snow Tubing: Nearby ski mountains like Jiminy Peak and Butternut offer snow tubing for all ages, ensuring fun and laughter for the whole family.

Ice Skating and Sledding: Visit local parks and rinks, such as the Pittsfield Common or the rink at Berkshire Community College, for classic winter activities.

Winter Hikes and Snowshoeing: Explore the snow-covered trails of Kennedy Park or Pleasant Valley Wildlife Sanctuary for scenic views and peaceful treks.

Cultural Attractions: Spend a day indoors visiting family-friendly spots like the Berkshire Museum, known for its engaging exhibits for kids and adults alike.

Festive Events and Markets: Depending on the season, enjoy winter festivals, holiday markets, and special performances at Tanglewood or Barrington Stage.

Farm-to-Table Dining and Cozy Cafés: Warm up with delicious meals at local restaurants or sip hot cocoa at charming cafés around Lenox and Great Barrin

Guest Reviews:

- "amazing! super great spot and not far from a ton of different places to go visit or hike or whatever else" - "Three of us had a great stay! The cottage was very clean and very well outfitted. It was clear that the hosts put a lot of thought into making sure guests would have everything they need. The space is bright and modern but still cozy, very nicely designed. The lake was a bit more of a walk than I had imagined it would be and there isn’t much of a sitting area by the lakefront but the lake itself is beautiful. Overall, a very nice cottage and lovely stay!"

Private Lake House in the Berkshires
House
Hinsdale, Massachusetts, USA

This lakefront property features a private sandy beach, dock, Goshen Stone walkways and fire pit, fenced-in yard, and 800 sq. foot deck. It boasts fantastic sunrise and sunset views from both the second and third floor lofts. Enjoy dining outdoors, with full use of the gas grill, meat smoker, and seafood/corn boiler. Cast your line directly from the dock, rinse off in the outdoor shower, explore the lake by kayak, and enjoy acres of hiking trails (within yards). Private off street parking and keyed use of neighborhood beach, picnic pavilion, and boat launch included.

Three bedrooms, three full baths, chef's kitchen, multiple living areas, central air conditioning, Wi-Fi, and an office for any vacation business needs. Towels, linens, and kitchen staples and cookware provided. Kayaks, floats, snow shoes, skates, life jackets, tent, air mattress, auger … are also available for use. Just a short drive to all the Berkshires has to offer. Tanglewood, Jacob’s Pillow, golf, skiing, museums, hiking, culture, and dining. (Baby equipment and misc. kids’ gear, including toddler mattresses, stroller, and kid kayaks also available.)

PLEASE NOTE: Some host reviews may be based on guests that stayed in the carriage house on the property. The home currently available for 2024 season is a lakefront, private home, with private beach and dock.

Guest Reviews:

- "This quiet property is located across the street from the owner, Mary. The apartment is very clean, well stocked, and Mary is very responsive. The lake is beautiful and can be accessed from Mary’s dock, the adjacent boat ramp, or the ‘beach’ which is a five minute walk, and I wish we could have spent a lot of time in it. However the weather did not cooperate with us, so we used the apartment as a home base for excursions north (Mt Greylock, art museums, Williamstown) or south (Tanglewood, Great Barrington area hiking and restaurants, Lee outlets). Hinsdale and Pittsfield do not have much to offer for restaurants or shopping beyond the usual chains so be prepared to drive 30-60 minutes."

Gorgeous Lake Ashmere Home with Private Hot Tub & Lake Views, Screened Porch
House
Hinsdale, Massachusetts, USA

Autumn Hill Lakehouse

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Nestled in the serene landscapes of Hinsdale, MA, this charming house is the perfect retreat for families and adventure seekers alike. Cherish the tranquility and natural beauty surrounding the property, making it an ideal getaway for those looking to escape the hustle and bustle of everyday life. With a spacious deck, a private hot tub, and a cozy firepit, guests can unwind while soaking in the stunning views and fresh air.

This home is designed for comfort and convenience, featuring modern amenities such as high-speed internet, a fully equipped kitchen, and a washer/dryer. Enjoy evenings grilling on the gas grill, gather around the outdoor dining area for a delightful meal under the stars, or enjoy a round of darts in the basement. The property also offers two kayaks available for use with various size life jackets.

Tucked into the trees across from Lake Ashmere, this home offers a private hideaway that’s still close to restaurants and shops. Find multiple golf courses and ski resorts in the area. Jiminy Peak is 19 miles away. Plus, you'll be near major events like Jacobs Pillow Summer Dance Festival and Tanglewood Concert hall summer home of the Boston Pop. With its family-friendly atmosphere and abundance of amenities, this Hinsdale getaway promises a memorable experience for everyone. Book your stay today and discover the charm of this delightful home!

House Rules

This Vacasa Guestworks vacation rental is operated and managed locally by an independent host.
Prior to your arrival, you will receive local host contact information, who will manage your guest reservation. Your local host will provide in-stay support, secure entry, and arrange pre- and post-stay housekeeping services.
If you need anything during your stay, the home’s independent local host is ready to help 24/7! Guestworks is a service offering of Vacasa that allows homeowners to smoothly and efficiently manage their own properties.

Parking notes: There is free parking available for 4 vehicles.

Security camera details: There is one active exterior camera facing the driveway.

Damage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.
More information can be downloaded from the "Rental Agreement" on the checkout page.

Due to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Guest Reviews:

- "We rented Autumn Hill Lake House to celebrate the 60th birthdays of 3 members of our group of 5 family members and close friends. The house was a perfect venue for us to spend a long weekend eating good food, playing games, reminiscing, and laughing. The house is beautiful with every amenity, spotlessly clean, and the most well-appointed rental I have ever encountered. Communications with the owner and the local host were efficient and seamless. We did not make use of the hot tub due to the weather (rainy and stormy all weekend) but the big screen TV with sound bar in the basement, the large selection of board games, the popcorn machine, and the cozy screened porch were big hits. The beds were very comfortable. It was pretty hot and humid during our stay. Although the ceiling fans and floor fan were helpful, it was a bit uncomfortable at times, although the basement was wonderfully cool. A/C or a whole house fan would be a welcome addition. That was really the only negative and it was a relatively minor one at that and was far outweighed by all of the positives. Would very highly recommend and would definitely consider returning. Wonderful home and a memorable weekend. Thank you."

Ashmere Lakefront Apartment
Apartment
Hinsdale, Massachusetts, USA

Second floor one bedroom/ one bathroom apartment overlooking Lake Ashmere Docks and Lake . Enjoy kayaking or paddle boarding(some available to our guests) on this pristine lake . Great Lake get away or a drive away to major Berkshire County attractions such as Jacobs Pillow, Tanglewood, biking trails, hiking trails, and many more.
Cozy apartment has all the comforts of home. Fully applianced kitchen , Brand new king mattress in bedroom and new queen pullout couch in living room. Enjoy Cable TV and internet.
Beautiful views can be enjoyed just sitting on the deck.

Guest Reviews:

- "Wonderful stay-comfortable bed with well equipped kitchen Paddleboards & kayaks were fun Nice living room area with porch & lake view Would definitely go back" - "We stayed here while dropping our son at school. Very easy to access and very private. Restful property with great lake views! Owners were fabulous!" - "This apartment is in an amazing location, looking over a peaceful lake. I found the apartment in immaculate condition and the owners to be very pleasant, helpful people. The area was very quiet day and night and the surrounding area very scenic."

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
House
Hinsdale, Massachusetts, USA

Bedroom with large master bath. Lockoff room with private front entrance. Kayak, swim, or bring your paddleboard or boat. Feed the ducks and enjoy the Egrets and Eagles. Use the front or back stone patios to relax or sit on the dock for splendid sunsets. Closeby beach and Association Pavillion is avialable or use our private Lakefront. Off street parking, very safe and quiet. Master bathroom with whirlpool tub / shower. High speed internet for TV or business. Beautiful flowers in the summer, Fall Foliage is spectacular and multiple ski areas nearby. With the provided mini fridge and microwave / airfryer why stay in a small hotel room? There are many Hiking trails including the Appalachian and also one by a stream within 1 mile. Close to all Berkshire attractions such as Tanglewood, Jacobs Pillow, Norman Rockwell museum, Mass MOCA, Mount Greylock, Etc,

Guest Reviews:

- "Basic hotel room experience. Comfy bed! Great shower. I only slept there, so I can’t comment on the lake or deck area. Only thing - I could hear their TV through the wall but it didn’t bother me!" - "We enjoyed the peace of the lake in between our adventures around the Berkshires. Thank you!" - "Beautiful property. Friendly hosts. Stocked with everything you should need. Plenty of outdoor space to enjoy the scenic surroundings. I recommend staying at Rich's place."

Berkshires Log Cabin by Evergreen Home
Cabin
Washington, Massachusetts, USA

The ultimate escape to peace & tranquility in the Berkshires! Set on 1.3 private acres, this cozy log cabin getaway is close enough to the action if you want it - and far enough away that you can feel disconnected from it all. Enjoy the large wraparound porch with sunset views. Drive 10 minutes to Becket Town Beach, 25 minutes to Tanglewood and 20 minutes to Jacob's Pillow. Ski nearby at Canterbury Farm & Bousquet Mountain. Includes 2 parking passes for lifeguarded Becket Town Beach (1 per car)

If you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.

Private and rural neighborhood.

Guests will have private access to the entire home, and property.

The first floor of this charming log cabin opens up to the great room with vaulted ceilings and a wood stove for cold winter days. A large sectional in the living pulls out to accommodate an additional 2 guests and the TV includes Roku and Netflix. The open concept kitchen is well stocked with everything you need for a meal at home and includes new stainless steel appliances. The kitchen table functions as a dining area and expands to seat 6 people.

The two bedrooms are both located on the first floor. The first includes a queen sized bed and work from home desk with fiber optic wifi. The second bedroom contains two twin beds. The full bathroom is also on the first floor and features a tub/shower combo.

Stairs to the loft area are set up as a ship stair design and may be difficult for some to navigate. The loft includes a queen sized pull out sofa that can be used as an additional bedroom. This space also has an additional workspace that can be used for both work and as a place for games and puzzles. The final feature of the loft is the ensuite bathroom will a clawfoot tub.

The laundry unit is located in the basement of the cabin.

Enjoy the total relaxation offered in the spacious and tranquil backyard of this charming log cabin.The front porch wraps around the home, and is quiet and tranquil to enjoy morning coffee and the evening sunset. Take a nap in the hammock or gather with your friends and family around the outdoor fire pit. There is also a BBQ and picnic bench for guest use as well as an outdoor private shower with hot and cold water.

Drive 10 minutes to Becket Town Beach, 25 minutes to Tanglewood and 20 minutes to Jacob's Pillow. Includes 2 parking passes for lifeguarded Becket Town Beach (1 per car)

In the winter enjoy the many ski resorts in the Berkshires including a 8 minute drive to Canterbury farm, 28 minutes to Bosquet mountain, 39 minutes to Butternut, 38 minutes to Jiminy Peak, and 24 minutes to Otis Ridge.

Having a car will greatly enhance your ability to explore the Berkshires effectively.

LOCATION: Private and rural neighborhood.
PETS: A small/medium sized dog may be allowed with owner approval. Reach out with info about your pet prior to booking. A $100 pet fee will be inccured upon pet approval and booking. No multiples.
PARKING: Free parking on premises.
*Please see photos of interior stairs to loft. They are built like ship stairs and may be challenging for some to navigate. The loft space can also be accessed from an exterior staircase with a traditional stair design.
*This property can accommodate 8 guests total. The living room sofa also pulls out to a sofa bed. Please reach out if you wish to have more than 6 guests stay, upon approval an extra fee may be incurred for the additional guests.

**Your reservation includes a $20 insurance fee to cover any accidental damage during your stay, allowing you to relax and enjoy your vacation with peace of mind. If any damage does occur, please let us know so we can arrange timely replacements for the next guest.

Guest Reviews:

- "My husband and I spent July at the property in Washington, MA just North of Becket. We were in the area to take advantage of all of the great culture--Jacob's Pillow, Tanglewood, Shakespeare & Co, etc. This property is very well located for getting to and from all of those venues and is not too far from Mass MOCA and the Clark (45 minutes). The property manager was very responsive when there were issues and in a full month stay there are bound to be some. Take the warnings about the stairs very seriously. For getting upstairs, there is an option to use the outside stairs rather than the indoor uneven stairs but to get to the basement where the trash and laundry are located, you have to take the uneven steps and there is also a low ceiling so we recommend this for people who are in decent shape and nimble. The property is kept very clean and the outdoor shower was a nice plus."

Hummingbird Haven is a Berkshires Retreat surrounded by Nature and Local Charm.
House
Hinsdale, Massachusetts, USA

Hummingbird Haven is a thoughtfully designed 3,100-square-foot home crafted for comfort, creativity, and connection—with plenty of space to spread out, come together, or simply unwind. Whether you’re here for a quiet retreat, a working getaway, or an adventure-filled vacation, this home offers the warmth and flexibility to make your time in the Berkshires truly special.
The home includes:

• Four large bedrooms, each with its own en suite full bathroom, complete with toiletries for your convenience.

• Two spacious living rooms, one with a beautiful stone gas fireplace, both with smart TVs for relaxing movie nights. DVD player and many movies to choose from. A variety of games to play, and chocolates and popcorn to snack on.

• A third, cozier living room with a piano, yoga equipment, and an electric fireplace—perfect for quiet mornings or mindful movement.

• An open-concept kitchen and dining area, ideal for gathering, cooking, and sharing meals.

• A fully equipped kitchen with plenty of dishes, cookware, a waffle maker, panini press, blender, toaster, convection oven, microwave, and more—it’s got everything you need to cook with ease.

• Three coffee maker options—French press, drip, and Keurig—plus coffee supplies to keep you caffeinated and happy.

• A generous welcome basket, snacks in the pantry, and thoughtful touches throughout to make your stay effortless and welcoming.

• A private home office with dual-screen monitors, a computer, high-speed fiber-optic Wi-Fi, and space for two to work comfortably.

• A spacious back deck wrapped in solar string lights and hop vines, with seating for eight, a propane grill, and grill utensils included.

• An outdoor fire feature, with everything you need for magical evenings under the stars.

• Lush perennial gardens, full of life with hummingbirds, monarch butterflies, and other friendly pollinators.

• Twinkle lights and magical ambiance throughout the home, plus gorgeous houseplants and a front porch with rocking chairs for peaceful moments.

Whether you’re seeking a restorative retreat, a productive working getaway, or a joyful, adventure-filled vacation, Hummingbird Haven offers the space, heart, and hospitality to make your stay in the Berkshires truly memorable.

Other things to note:

Local Attractions, Dining & Entertainment

Hummingbird Haven is centrally located in the beautiful Berkshires, offering easy access to arts and culture, outdoor adventure, skiing, live entertainment, and exceptional dining—all just a short drive from your door.

Arts & Culture
• Tanglewood – Iconic summer home of the Boston Symphony Orchestra with open-air concerts in Lenox.
• Jacob’s Pillow Dance Festival – World-renowned performances and workshops in nearby Becket.
• Norman Rockwell Museum – A must-see collection of the beloved American illustrator’s work in Stockbridge.
• Berkshire Theatre Group – Acclaimed plays and musicals in both Pittsfield and Stockbridge.
• Shakespeare & Company – Powerful live theatre in an intimate Lenox setting.
• MASS MoCA – Large-scale contemporary art installations in North Adams.

Outdoor Adventure & Skiing
• Wahconah Falls State Park – A scenic waterfall and walking trail just 10 minutes away.
• October Mountain State Forest – Hiking, kayaking, and panoramic views across the Berkshires.
• The Appalachian Trail – Access nearby trailheads for iconic hikes.
• Big Pond (Otis) – Local favorite for swimming, fishing, kayaking, paddleboarding, and lakeside picnics.
• Ashmere Lake – Located just down the road—great for swimming, fishing, paddling, or peaceful reflection.
• Otis Ridge – Family-friendly ski mountain with charm and affordable lift tickets (~20 minutes away).
• Jiminy Peak Mountain Resort – Full-service ski resort offering trails for all levels, plus summer adventure parks (~40 minutes away).

Live Entertainment & Events
• The Stationery Factory (Dalton) – A unique venue hosting live music, art shows, and local events.
• Colonial Theatre (Pittsfield) – Historic landmark with concerts, comedy shows, and Broadway-style performances.
• Bousquet Mountain (Pittsfield) – Year-round fun: skiing in winter; mountain coaster, concerts, and events in summer.
• Barrington Stage Company – Innovative, award-winning theatre productions in downtown Pittsfield.

Dining & Sweet Treats Nearby
• Ozzie’s Steak & Eggs (Hinsdale) – Local favorite for breakfast and lunch with hearty, homemade comfort food.
• Sibaritas (Pittsfield) – South American–Italian fusion with flavorful dishes and a cozy, friendly vibe.
• Rare 297 Steakhouse (Pittsfield) – Elegant steakhouse with premium cuts, sushi, and a vibrant cocktail scene.
• Mint (Lee) – Romantic lakeside dining with seasonal menus and fresh ingredients.
• Patrick’s Pub (Pittsfield) – Laid-back, kid-friendly restaurant with pub classics and rotating craft beers.
• Once Upon a Table (Stockbridge) – Intimate bistro serving seasonal fare in a storybook New England town.
• Chocolate Springs Café (Lenox) – Artisan chocolates, mousse cakes, gelato, espresso, and hot chocolate in a stylish café setting—perfect for an afternoon indulgence.
• Guido’s Fresh Marketplace (Pittsfield) – Upscale grocery store offering fresh produce, prepared meals, specialty items, and everything you need to stock the kitchen during your stay.

Guest Reviews:

- "This property was amazing! Very clean and spacious, perfect location for a nice peaceful getaway. Kendra was very communicative and made sure our stay was comfortable. 10/10 highly recommend you to stay here. " - "This is a great house with plenty of comfortable spaces in which to sleep and relax. Host Kendra was incredibly welcoming, attentive, and reachable before during and after our stay. Any question we had was responded to within minutes. The house is very clean and equipped with any and everything you might need during your stay from kitchenware to stationary to a Gasx for an upset stomach. I recommend this house with no Hesitations! "

Centrally located in the Berkshires - Cozy Bungalow in SE Pittsfield!
House
Pittsfield, Massachusetts, USA

New listing ! Looking for a centrally located place to stay? This Berkshires home is 5 minutes from Bousquet Ski Resort , 20 minutes from Jiminy Peak, and minutes from hiking and museums.
Tanglewood in Lenox only 15 minutes away. Hang out on the deck, play yard games and cook out on the grill with friends and family.

Guest Reviews:

- "It was a convenient location for visiting Tanglewood and the kitchen is perfect for packing picnics. Lovely neighborhood too!" - "We were SO happy with our stay! The house is absolutely adorable, situated on a quiet dead end street with a big yard/deck, and communication with the host was seamless. The house is nicely decorated, is outftted with anything you could ever need (even games which our kids loved!), and was IMMACULATE. Beds were super comfy too. We frequent the Berkshires often and look forward to staying here again!"

Pittsfield Home w/Deck - 12 Mi to Jiminy Peak!
House
Pittsfield, Massachusetts, USA

Great for outdoor enthusiasts, this 3-bedroom, 2.5-bathroom vacation rental home features a balcony, a deck, a patio, and a gazebo for you to enjoy. With a Smart TV, fireplace, and in-unit laundry, this Pittsfield retreat will make you feel cozy as soon as you arrive. After settling in, head out to wander around the town and visit Park Square or Pittsfield State Forest. Then, shred some powder at Bousquet Mountain Ski Area before returning to this getaway to stargaze on the patio.

-- THE PROPERTY --

MassTaxConnect ID: C0449692360 | Gas Grill | Fireplace

Bedroom 1: King Bed | Bedroom 2: Queen Bed, Full Bed | Bedroom 3: 2 Queen Beds

HOME LIVING: Fireplace, Smart TV, washer/dryer, balcony, patio, outdoor sitting area, gazebo
KITCHEN Dishwasher, fridge, stovetop, 2 ovens, microwave, coffee maker, dining table, cooking basics, dishware & flatware, Crockpot
GENERAL: Free WiFi, ceiling fans, central heating, linens, towels, complimentary toiletries, hair dryer, hangers, iron/board, trash bags, paper towels, high chair
FAQ: 2 steps required, bedroom/full bathroom on 1st floor, 2 exterior security cameras (facing out), no A/C
PARKING: Driveway (2 vehicles)

-- THE LOCATION --

LOCAL SPOTS: Park Square (4 miles), Colonial Theatre (4 miles), Berkshire Museum (4 miles), Lake Onota (8 miles), Hancock Shaker Village (9 miles)
OUTDOOR RECREATION: Ashuwillticook Rail Trail (1 mile), Springside Park (4 miles), Pittsfield State Forest (8 miles), Mount Greylock State Reservation Visitor Center (8 miles), October Mountain State Forest (13 miles)
WINTER WONDERLAND: Bousquet Mountain Ski Area (8 miles), Jiminy Peak Mountain Resort (12 miles), Berkshire East Mountain Resort (29 miles), Catamount Mountain Resort (36 miles)
AIRPORTS: Albany International Airport (51 miles), Bradley International Airport (57 miles)

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE The property requires 2 steps to access
- NOTE: The property has ceiling fans but does not offer air conditioning
- NOTE: Your safety matters. This property features 2 exterior security cameras. Camera 1 is located in front of the garage facing the driveway, and camera 2 is located at the back patio facing the backyard. The cameras are outward facing and do not look into interior spaces. The cameras record video when activated by motion while guests are in residence

Guest Reviews:

- "This was an amazing rental everything was amazing, I can't wait to book this property again" - "We booked this property with our friends for a ski holiday. The place was perfect in size for our group. Kitchen was equipped with everything we needed for cooking and cleaning. Between the living room and family room, kids had room to play and entertain. Host was very quick to respond. Check-in and check-out was a breeze.Overall, it was a very good place for us to stay for our holiday."

Family-Centric Berkshire Getaway by Evergreen Home
House
Pittsfield, Massachusetts, USA

This renovated 4 BR ranch located just minutes from Lenox has everything your family needs for a relaxing getaway! Ideally located in Central Berkshire County; museums, skiing, lake life, hiking, theaters and shopping are all just a short drive away. When you're home, relax with a movie in our theater room, play corn hole in the spacious back yard, bbq on the grill, how about a game of Foosball or Pac-Man? With room for 6 adults or 8 w/kids, this lovely spot is your perfect family retreat!

If you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.

This house is ideally located in Central Berkshire County, close to many activities and features a spacious private backyard.

Guests have full access to the house excluding utility room.

This renovated ranch home features an open concept kitchen with stainless steel appliances fully equipped for making meals at home. The dining area seats six guests with an additional three stools at the bar and offers views of the spacious backyard. This home has 4 large screen TVs. All sofas are in the lower level, but comfortable seating has been supplied for the TVs on the main level including a large plush leather chair in the primary bedroom and a recliner in the dining room/sitting room.

The primary suite on the main floor contains a king sized bed and walk in closet. The connecting bathroom features a beautiful new walk in shower. The second and third bedrooms, also on this level, both contain queen sized beds. The 4th bedroom has a pullout sofa/futon which can fit 2 kids or 1 adult. If only adults are staying, then only 6 guests are allowed. The guest bathroom includes a shower/tub combo.

The lower level family room includes one of the four TVs, two comfortable sofas, as well as foosball and pac man. The theater room is also on this lower level with a reclining sofa and additional bar stool seating. Exiting the family room through the sliding door takes you right outside to the backyard.

Dine outside with the outdoor dining set on the deck and BBQ on the patio with a large umbrella to provide shade.

This home is located only a few minutes to Lenox. 27 Minutes to Jimmy Peak, 33 minutes to Butternut Ski Area/Great Barrington. 10 minutes to the Colonial Theater (BTG) and Barrington Stage Theater and 14 minutes to Tanglewood and Miraval Resort.

You will need a car to get around the Berkshires effectively.

LOCATION: This house is ideally located in Central Berkshire County, close to many activities and features a spacious private backyard.
PETS: No pets are allowed.
PARKING: Free parking on premises.
*Parents, please note that while the house has an expansive back yard, it is not fenced in and the front of the house pretty close to the road. It is not an especially busy street, but little ones will need to be watched.
*There will be a charge of $30 per day, per car if you charge your electric car at the house.

Guest Reviews:

- "Great stay" - "We had a lovely time at this cozy place" - "We loved our stay, and our extended family was well accommodated! More than enough bedrooms and bathrooms for all, and the lower level recreation rooms were a plus. The kitchen was spacious too and well appointed with all cooking and serving amenities provided. It was a cheerful and upbeat space, and beds were comfortable. We look forward to returning!"

Waterfront Ashmere Lake House Near Berkshire Attractions
House
Hinsdale, Massachusetts, USA

Waterfront property on Ashmere Lake in Hinsdale, MA, with 4 bedrooms, an office, 3 bathrooms, screened in porch and a beautiful dock. Finished basement with ping-pong table. Two double kayaks and 2 single kayaks, a fire pit and wonderful view. Shopping located in nearby Pittsfield,
approximately 20 minutes from Tanglewood, Jacobs Pillow, Waconah Falls, summer theater venues, and Lee outlets. Wifi and 3 TV's.

Guest Reviews:

- "We had a wonderful vacation on Ashmere Lake! The house was beautiful, immaculate and well appointed. Debra made sure we had everything we needed to make our stay enjoyable. We enjoyed kayaking, floating on the lake or just relaxing on the dock taking in the gorgeous view. There is so much to do in the area.....museums, Tanglewood, nature hikes and waterfalls just to name a few. Such a relaxing vacation!" - "Everything was perfect. The home is clean, organized, stocked with everything anyone could possibly need. Our favorite part was the screened porch area. We sat outside during the rainstorms playing card games - we loved the many separate areas to sit and relax. If you’re looking for a lovely place to relax, THIS IS IT!!"

Getaway w/Game Room & Theatre
House
Pittsfield, Massachusetts, USA

Movie buffs unite! This home comes designed specifically as the perfect getaway. Featuring three comfortable bedrooms, two newly appointed bathrooms, and a spacious backyard, this spot is ideal for relaxation and fun. Step outside and enjoy the full deck with a grill and outdoor dining area. Every detail has been meticulously thought through at this spot to make it THE PERFECT getaway destination just minutes to both downtown Lenox and Pittsfield. Book your stay today!

Things You’ll Love

– Berkshire Vacation Rental standard: coffee, creamer, fresh linens, towels, and toiletries.
– A game room and private home theatre for fun nights in.
– Spacious backyard with a full deck, grill, and outdoor dining area.
– Outdoor fire pit with chairs, perfect for cozy evenings under the stars.

Welcome to your ideal Berkshires getaway! Centrally located, just minutes from downtown Pittsfield and Lenox, this charming home is nestled along a peaceful country road with a spacious yard for outdoor fun. Inside, the main living area features a comfortable living area, a dining table for six, and a cozy breakfast nook nestled into the kitchen. The fully stocked kitchen, a cooks dream, comes complete with a dishwasher and all the necessary cooking utencils, is perfect for creating delicious meals. The luxurious master suite offers a king-sized bed, a wall mounted big-screen TV, and direct access to a modern, tiled bathroom with his-and-her sinks.

Down the hall, you'll find two guest bedrooms—one with a queen bed and another with a double—plus a stylish guest bathroom, providing ample space for family or friends.

The real highlight of the home is the lower level, where relaxing and entertainment come together seemlessly. A fully blacked-out movie theatre invites movie buffs to relax and enjoy screenings, while the game room features a foosball table, Pac-Man, and a drinks area for reminiscing about the days adventures.

Lastly, step outside to the back patio, equipped with an outdoor dining set and gas grill, perfect for entertaining and enjoying the fresh Berkshire air. This home combines comfort, convenience, and fun, creating an unforgettable base for your vacation in the Berkshires!

The home is perfectly situated in the southern Pittsfield area with easy access to both downtown Pittsfield and downtown Lenox. The house is set on a smaller country style road with lots of space between neighbors and a large backyard to enjoy all to yourselves.

For outdoor recreation, look no further than Canoe Meadows, Bousquet Ski Area, Kennedy Park, and the many other sites for hiking, cycling, and swimming in the area.

For the arts enthusiast, Tanglewood is a ten minute drive to the south, while Barrington Stage's main theatre is ten minutes to the northeast.

***This is a pet free home. We keep it this way so that we can rent to guests with specific needs. If you need to bring a pet along, please reach out to us, and we will be happy to set you up with another property of ours that is pet friendly.
- no smoking inside
- no overnight guests beyond those listed in the booking
- no street parking
- This is a pet free home. We keep it this way so that we can rent to guests with specific needs. If you need to bring a pet along, please reach out to us, and we will be happy to set you up with another property of ours that is pet friendly.

If you break anything, let us know right away and we'll work with you!

Amenities:

Air Conditioner • Sports/Activities • Fireplace/Heating • Laundry • Other • Security/Safety • Entertainment • Child Friendly • Tv • Kitchen • Bedding/Linens • Balcony/Terrace

The Perfect Escape; Log Cabin situated on 40 Secluded Acres of Wilderness
Cabin
Peru, Massachusetts, USA

https://www.partridgehillberkshires.com/

Under 3 hours from New York City and Boston, find yourself immersed in a four season property designed with relaxation and privacy in mind. This 3 bedroom, 2 bathroom tastefully decorated log cabin is a haven from the hustle and bustle of it’s surrounding cities.

You and your guests will enter through the front porch into the Great Room, a spectacular open living space with cathedral ceilings over 16 ft high. Let the outside in with private vista views from the bay windows and double french doors. Warm yourself by the stone hearth fireplace also 16ft in height or open the french doors to the wrap around deck letting the fresh air in. The main floor is also equipped with a chef style open concept kitchen, including a Viking range, stainless steel appliances, and granite counter-tops. With a vintage wooden dining table set for six overlooking the entire Great Room, you will never miss out on time spent with family and friends.

Two floors of finished living space and sweeping wrap around decks will provide you with more than enough room for the entire family. The house will sleep 6 in secluded bedrooms and 2 additional guests on the queen pull out couch.

Amenities:

Bedding/Linens • Kitchen • Fireplace/Heating • Balcony/Terrace • Sports/Activities • Pool • Tv • Internet • Hot Tub • Security/Safety • Other • Laundry

Berkshire Cabin by Lake Ashmere
Cabin
Hinsdale, Massachusetts, USA

Come stay at this comfortable, private cottage at Lake Ashmere in the Berkshires. There’s lake access with a short walk across the street to a private beach where you can swim or take out one of the two kayaks provided.

You're also close to:
Tanglewood
Mount Greylock
Jiminy Peak Resort
Ioka Valley Farm
The Adams Theater
Ashuwillticook Rail Trail
Whitney's Farm Market (great for kids)
Hancock Shaker Village

Amenities:

Child Friendly • Parking • Kitchen • Fireplace/Heating • Bedding/Linens • Internet • Tv • Wellness Facilities • Security/Safety • Balcony/Terrace

Beautiful Renovated Home, Close to Multiple Ski Mountains.
House
Hinsdale, Massachusetts, USA

Great, recently renovated Berkshire Escape. Set on 6 acres with plenty of outdoor space and trails to enjoy in the warmer months. Plenty of room for the entire family or quiet getaway for a couple. Location is close to Lenox, Dalton Jimmy Peak and Bosquet ski area.

Amenities:

Child Friendly • Security/Safety • Pet Friendly • Bedding/Linens • Laundry • Air Conditioner • Internet • Other • Fireplace/Heating

Large open floor plan. Private yet close to everything. Lovely meadow views
House
Pittsfield, Massachusetts, USA

Get ready to relax in this 6-bedroom house in Pittsfield. This welcoming property boasts 4 queen beds, 1 king bed, 1 twin bed, and 1 full bed, perfect for a terrific getaway with friends or family. With 4 bathrooms equipped with a hairdryer, shower, and bathtub, guests can unwind in marvelous comfort. Experience what Pittsfield has to offer with a stay at our house.

Amenities:

Barbecue/Outdoor Cooking • Internet • Bedding/Linens • Tv • Kitchen • Laundry • Air Conditioner • Parking • Security/Safety • Child Friendly • Fireplace/Heating • Wellness Facilities

Lakeside Getaway
Apartment
Hinsdale

Lakeside respite awaits you in this comfortable getaway by the lake. Easy access to major Berkshire attractions, but tucked out of the way. Private patio includes a fire pit and view to the lake. Enjoy an easy walk to our private docks with kayaks available for renters. The guest suite includes a bedroom with a queen-sized bed, a sitting room with an optional floor mattress, eat-in counter and kitchenette, and a full bath. The suite has a private entrance and is locked off from the main house.

The space
The guest suite includes a bedroom with a queen-sized bed, a sitting room with an optional floor mattress, eat-in counter and kitchenette, and a full bath. The suite has a private entrance and is locked off from the main house.

Guest access
You will have complete and private access to a bedroom, full bathroom, and sitting room. You also have a private patio with a wood-burning firepit. You will also have access to our dock and kayaks.

Other things to note
ABSOLUTELY NO SMOKING OR VAPING of any substances inside the apartment. PLEASE respect this rule as it compromises the health of the resident in the main house.

Amenities:

Shower gel • Hangers • Bed linens • Cleaning products • Extra pillows and blankets • Hot water • Body soap • Room-darkening shades • Hair dryer • Shampoo

Berkshire sunset lakefront
House
Hinsdale

Relax in the spacious room with private Master Bath and whirlpool. Kayak from our dock, swim, fish and feed the ducks on the over 200 acre Lake. Gorgeous sunsets, many seating areas on the hillside leading down to our lake frontage. Front and rear bluestone patio areas.

The space
The room has sole access via the home front door. Owners use side door for their space. Very quiet. Walkways around either side of home to patio area overlooking lake and stairway to dock. Kayaks available or bring your own paddleboard.

Guest access
Their room, front porch, front and back patios, hillside seating areas, and dock.

During your stay
We reside in the back portion of the home and are available always.

Other things to note
It maybe possible to bring your own boat and launch at the lake association dock.

Amenities:

Essentials • Body soap • Hangers • Lake view • Conditioner • Bathtub • Cleaning products • Hair dryer • Hot water • Shampoo

Beautiful 2-BR + Loft w/ Hot Tub at Lake Ashmere
Cabin
Hinsdale

Welcome to Lake Ashmere!

Our newly and completely renovated cottage features two bedrooms with comfy queen size beds, a loft with two full size beds, cathedral ceilings, a year-round six person hot tub and a large working kitchen stocked with everything you need. The living space is bright and airy. WiFi in the cottage is over 500 mbps, making it ideal for longer stays. The spectacular lake is just a three-minute walk from the cottage.

The space
Set in a peaceful location, the cottage is just a three minute walk to Lake Ashmere where you can relax and enjoy the lake. We have two kayaks and tubing for your easy access to use on the lake.
Nestled in the scenic foothills, our home offers a perfect blend of relaxation and adventure, with endless summer activities right at your doorstep.

Outdoor & Adventure:
Spend your days exploring the natural beauty of the region with a range of outdoor activities. Take a hike through the nearby trails, including those at October Mountain State Forest or Berkshire Natural Resources Council trails. These trails offer both leisurely walks and more challenging hikes with stunning views of the surrounding mountains. If you're looking to relax by the water, head over to Onota Lake, just a short drive away. Here, you can enjoy kayaking, paddleboarding, or just lounging by the shore.

Music & Cultural Events:
Summer in the Berkshires means music, art, and culture at every turn. Take in a concert at the Tanglewood Music Festival, the summer home of the Boston Symphony Orchestra, located just a short drive away in Lenox. Whether you love classical music or contemporary performances, Tanglewood offers an unforgettable experience. For a more intimate vibe, check out the local music scene with outdoor concerts, jazz, and folk music festivals hosted at local venues like The Colonial Theatre in Pittsfield and Jacob's Pillow Dance Festival in Becket.

Fine Dining & Local Cuisine:
Food lovers will delight in the variety of delicious restaurants and farm-to-table eateries in the Berkshires. Enjoy a gourmet meal at The Red Lion Inn in Stockbridge, or explore the eclectic menu at The Prairie Whale in Great Barrington. For a casual bite, grab a local treat at one of the charming cafés or farm stands in Hinsdale. Don’t forget to try some of the region's finest craft beer at one of the nearby breweries.

Local Attractions & History:
Explore the rich cultural history of the Berkshires, from the Norman Rockwell Museum in Stockbridge to the historic sites scattered throughout the area. A visit to the Shakespeare & Company theater in Lenox is perfect for a night out or enjoy the beauty of the Berkshire Botanical Garden.

Whether you're a nature enthusiast, music lover, or food connoisseur, Hinsdale offers something for everyone. After an exciting day of activities, retreat to your peaceful home and enjoy breathtaking sunsets, quiet nights, and a relaxed pace that defines this picturesque corner of Massachusetts.

Soak your cares away in our private 6-person hot tub, the perfect way to ease tired muscles and enjoy the cool evening air under the stars.

Book your stay now and create unforgettable memories in the Berkshires!

Guest access
The entire home, backyard and lake just down the street. The lake has a boat ramp which is easily accessible, as well as a picnic table just steps from the lake, and available for the use of our guests.

Relaxing Berkshire cabin on Lake Ashmere
Cabin
Hinsdale

Are you seeking a relaxing retreat in the Berkshires? Our 2 BR lakehouse offers a comfortable experience, featuring a knotty pine kitchen, a new wood stove, outdoor fire pit, kayaks, comfy beds, and a fully-stocked coffee bar. Nestled among trees on the edge of Lake Ashmere, the lakehouse is the ideal setting for a central Berkshire getaway, especially during fall foliage season (peak is early Oct). Conveniently located, it's a 15-min drive to Pittsfield and 30 mins to Jiminy Peak or Tanglewood.

The space
The property, situated on approximately one-third of an acre, offers views of Lake Ashmere through the trees. Direct access to the lake provides a stunning perspective from the landing, ideal for enjoying sunsets. This two-story residence features two bedrooms on the upper level, with a living room, galley kitchen, dining area, and bathroom on the lower level. Fully renovated in 2021, the home is equipped with modern amenities including a security system, dimmable lighting, Wi-Fi, a smart TV, and a smart lock. The home's lake-facing orientation, complete with a large picture window and sliding glass doors, maximizes the scenic views. A spacious wrap-around deck, furnished with a patio set and gas grill, enhances the outdoor living experience. The property also includes a well-maintained front yard and a fire pit area. Direct access to the lake is easily accessible via a gentle slope.

Guest access
Guests are encouraged to explore the surrounding area via pedestrian access, bicycle, or personal vehicle. Parking is available in the driveway for a maximum of three vehicles. The lake is situated a brief one-minute walk from the property.

Other things to note
Lake Ashmere is in the upper middle part of the Berkshires and the lake is used for kayaking, jet skiing, fishing and swimming in summer, or maybe snowmobiling or ice fishing in winter. Our favorite time of year is fall and to witness the change of leaves in late September/early October just takes your breath away.

We are close to most popular Berkshire attractions (Tanglewood, Mt. Greylock, Butternut, Berkshire East, Bousquet, Canterbury Farm, Stockbridge, Norman Rockwell Museum, MoCA, Clark Art Institute, Catamount Ski Area, Berkshire Botanical Gardens, Naumkeag, Hancock Shaker Village) and so much more! You would not be without things to do and see if you stayed here for a week!

Amenities:

Free washer – In unit • Honest body soap • Free dryer – In unit • Lake view • Essentials • Cleaning products • Shampoo • Hair dryer • Hot water • Conditioner

Lakeside Serenity!
House
Hinsdale

Hummingbird Haven is a bright and spacious 4-bedroom retreat in the heart of the Berkshires. With 3,100 sq. ft., high ceilings, a cozy loft, and plenty of room to relax and unwind, it’s perfect for families, professionals, or friends. Enjoy nearby trails, beaches, and local culture—or stay in and unwind with games, sunlight-filled spaces, and a well-stocked pantry. A peaceful, year-round escape just minutes from it all.

The space
Hummingbird Haven is a thoughtfully designed 3,100-square-foot retreat built for comfort, creativity, and connection—offering generous space to gather, spread out, or simply unwind.

Inside, you’ll find:
• Four spacious bedrooms, each with its own en suite full bathroom and stocked with toiletries for your convenience.
• Two inviting living rooms, one with a beautiful stone gas fireplace, both equipped with smart TVs, a DVD player with a wide movie selection, a variety of games, and snacks like popcorn and chocolates for cozy evenings in.
• A third, cozier lounge, featuring an electric fireplace, yoga equipment, and a piano—ideal for quiet mornings or mindful movement.
• An open-concept kitchen and dining area, perfect for cooking, connecting, and lingering over shared meals.
• A fully stocked kitchen, complete with cookware, dishes, waffle maker, panini press, blender, toaster, convection oven, microwave, and more—everything you need to cook with ease.
• Three coffee makers—French press, drip, and Keurig—plus a generous coffee and tea station to keep you caffeinated and content.
• A private home office, equipped with high-speed fiber-optic Wi-Fi, dual-screen monitors, a computer, and space for two to work comfortably.
• A generous welcome basket, snacks in the pantry, and thoughtful touches throughout to make your stay feel effortless and personal. Magical ambiance throughout, with twinkle lights and houseplants adding warmth and charm to every space.

Outdoors, enjoy:
• A spacious back deck, wrapped in solar string lights and hop vines, with seating for eight and a large propane grill (grill tools included).
• A cozy fire feature, complete with all the essentials for starlit evenings including starter sticks, kindling, and firewood.
• Lush perennial gardens, alive with hummingbirds, monarch butterflies, and friendly pollinators.
• A peaceful front porch with rocking chairs, perfect for morning coffee or evening reflection.

Whether you’re seeking a restorative retreat, a productive working getaway, or a joyful, adventure-filled vacation, Hummingbird Haven offers the space, heart, and hospitality to make your stay in the Berkshires truly memorable.

Guest access
All access to home with the exception of the basement and garage for car storage.

Other things to note
🎭 Local Attractions, Dining & Entertainment
Hummingbird Haven is centrally located in the beautiful Berkshires, offering easy access to arts and culture, outdoor adventure, skiing, live entertainment, and exceptional dining—all just a short drive from your door.

🎨 Arts & Culture

• Tanglewood (Lenox) – Iconic summer home of the Boston Symphony Orchestra with open-air concerts in a stunning setting.

• Jacob’s Pillow Dance Festival (Becket) – World-renowned performances and workshops in a historic mountaintop theater.

• Norman Rockwell Museum (Stockbridge) – A must-see collection of the beloved American illustrator’s work.

• Berkshire Theatre Group (Pittsfield & Stockbridge) – Acclaimed plays and musicals in classic New England venues.

• Shakespeare & Company (Lenox) – Powerful live theatre in an intimate, rustic setting surrounded by gardens.

• MASS MoCA (North Adams) – Large-scale contemporary art installations in a massive, repurposed mill complex.

• The Stationery Factory (Dalton) – A former paper mill turned dynamic arts and events space with concerts, markets, and exhibitions.

⛰️ Outdoor Adventure & Skiing

• Wahconah Falls State Park – 4 miles / 10 min
A picturesque waterfall and forest trail just minutes away, perfect for a short walk or peaceful picnic.

• October Mountain State Forest – 10 miles / 20 min. Explore miles of hiking, mountain biking, kayaking, and sweeping views of the Berkshires.

• The Appalachian Trail – Multiple trailheads within 15–30 min. Iconic hikes and scenic views from one of America’s most treasured long-distance trails.

• Big Pond (Otis) – 14 miles / 25 min
Locals love it for swimming, fishing, kayaking, paddleboarding, and lakeside picnics.

• Ashmere Lake (Hinsdale) – Just down the road
Peaceful spot for swimming, fishing, canoeing, or simply relaxing by the water.

• Otis Ridge Ski Area – 14 miles / 20 min
Family-friendly ski mountain with old-school charm and affordable lift tickets.

• Jiminy Peak Mountain Resort (Hancock) – 26 miles / 40 min
Full-service ski resort with trails for all levels, plus summer adventure parks and alpine coasters.

• Bousquet Mountain (Pittsfield) – 12 miles / 20 min
Year-round recreation: ski slopes in winter; concerts, mountain coaster, and events in summer.

🎶 Live Entertainment & Events

• Colonial Theatre (Pittsfield) – Historic venue with concerts, comedy shows, and Broadway-style performances.

• Barrington Stage Company (Pittsfield) – Award-winning theatre company producing innovative dramas and musicals.

• Shire Breu-Haus (Dalton) – Rustic-chic brewery and gastropub with live music, craft beer, and community energy.

• The Stationery Factory (Dalton) – Also a hub for concerts, art shows, holiday markets, and special events.

🍽️ Dining & Sweet Treats Nearby
(All distances are from 140 Lenore Drive, Hinsdale, MA)

Hinsdale & Dalton

• Ozzie’s Steak & Eggs (Hinsdale) – 2 miles / 5 min
Local favorite for breakfast and lunch with hearty, homemade comfort food. Voted “Best of the Berkshires.”

• Porta Via (Dalton) – 4.5 miles / 8 min
Authentic Italian deli serving fresh paninis, pasta, salads, and imported specialties.

• Hot Harry’s Burritos (Dalton) – 4.5 miles / 8 min
Fresh, fast burritos, bowls, and tacos made with bold flavors and customizable options.

• Angelina’s Submarine Shop (Dalton) – 4.5 miles / 8 min
Classic, overstuffed subs and sandwiches with a loyal local following.

• Juice N’ Java (Dalton) – 4.5 miles / 8 min
Relaxed café for smoothies, fresh juices, coffee drinks, and light bites.

• Shire Breu-Haus (Dalton) – 5 miles / 10 min
Craft brewery and pub fare with live music and a laid-back atmosphere.

Pittsfield (8–9 miles / ~15 min)

• Sibaritas – South American–Italian fusion with flavorful dishes and warm hospitality.

• Rare 297 Steakhouse – Sleek steakhouse and sushi bar with premium meats and a lively bar scene.

• Patrick’s Pub – Cozy, family-friendly spot for burgers, wings, and local beers.

• Dottie’s Coffee Lounge – Artsy and welcoming café with exceptional coffee, teas, breakfast, and pastries.

• Guido’s Fresh Marketplace – Upscale grocery offering prepared foods, organic produce, and Berkshire specialties.

Lenox (16 miles / ~25 min)

• Frankie’s Ristorante Italiano – Elegant and cozy Italian spot with classic fare and excellent wines.

• Zinc Bistro & Bar – Stylish bistro with French-
influenced New American cuisine and a hip vibe.

• Chocolate Springs Café – A must for chocolate lovers: artisan truffles, cakes, espresso, and gelato in a sleek setting.

Lee & Stockbridge (15–16 miles / ~25 min)

• Mint (Lee) – Seasonal lakeside dining with creative cuisine and romantic ambiance.

• Once Upon a Table (Stockbridge) – Hidden gem serving local, artfully prepared dishes in a storybook setting.

• The Red Lion Inn (Stockbridge) – Historic inn with classic New England fare, charming taverns, and elegant dining rooms.

• The Lost Lamb Patisserie (Stockbridge) – Delightful French bakery with croissants, pastries, savory tarts, and espresso in a beautifully curated space.

Amenities:

Shower gel • Shampoo • Body soap • Conditioner • Cleaning products • Dryer • Hot water • Hair dryer • Washer • Bathtub

Autumn Hill Lakehouse
House
Hinsdale

The space
Autumn Hill Lakehouse

Experience the best of the Berkshires at this gorgeous lake house. An all-season retreat, your home is right across from Lake Ashmere and offers easy access to Jiminy Peak.

Incredible outdoor space abounds. The wraparound deck offers the perfect spot to sip morning coffee in the sunshine or cook out on the grill in the afternoons. Enjoy soaking in the private hot tub after a fun day on the lake or mountain. There’s even a screened porch for curling up with a good book.

Inside, gorgeous floor-to-ceiling windows showcase lake views from the beautifully designed open living area. Find everything you need to prepare delicious home-cooked meals in the sleek modern kitchen. Upscale stainless steel appliances include a gas range, double oven, and side-by-side fridge.

A lofted primary suite overlooks the living area and boasts lake views. Find even more social space in the family room, which features a large TV and board games. The home office offers convenient amenities for those looking to work, including high speed internet, a color inkjet printer, sit to stand ergonomics, and phone charging.



Your home is tucked into the trees across from Lake Ashmere, offering a private hideaway that’s still close to restaurants and shops. Find multiple golf courses and ski resorts in the area. Jiminy Peak is 19 miles away. Plus you'll be near major events like Jacobs Pillow Summer Dance Festival and Tanglewood Concert hall summer home of the Boston Pop.

House Rules

This Vacasa Guestworks vacation rental is operated and managed locally by an independent host.
Prior to your arrival, you will receive local host contact information, who will manage your guest reservation. Your local host will provide in-stay support, secure entry, and arrange pre- and post-stay housekeeping services.
If you need anything during your stay, the home’s independent local host is ready to help 24/7! Guestworks is a service offering of Vacasa that allows homeowners to smoothly and efficiently manage their own properties.
No dog(s) are welcome in this home. No other animals are allowed without specific Vacasa approval.

Parking notes: There is free parking available for 4 vehicles.






Damage waiver: The total cost of your reservation for this Property includes a damage waiver fee which covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. More information can be found from the "Additional rules" on the checkout page.

Due to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Modern Lakehouse with Private Lake Access
House
Hinsdale

Clean style and calming stay, this is an all-season home with private access to Lake Ashmere - a hidden gem within the Berkshires boasting frequent activity yet remaining private and tranquil. Enjoy the summer water, fall foliage, or winter ice depending on when you stay.

The home is located with easy access to various other Berkshire amenities such as Jiminy Peak, Bousquet Mountain, golf courses, hiking trails, along with being only 25 minutes from locations such as downtown Lenox.

The space
The space itself was designed to be modern, functional, and spacious - including an open floor plan and large outdoor decks to experience nature and views of the water. You'll find your stay here to feel refreshingly simple.

This property and its lake access is owned by Heron Hideaways, LLC.

Guest access
You'll have access to the entire home as well as Ashmere Lake. The home itself is equipped with a lockbox - you will receive the code prior to your stay. Feel free to fully utilize the home and the area - bring your boat, paddleboards, kayaks, snowmobiles, fishing gear (for summer water or winter ice), etc. There is plenty of parking at the home that should comfortably fit 3-4 vehicles if needed. The access to the lake includes a boat launch and private area - feel free to pull up your car or take the quick 2 minute walk to either location.

Other things to note
Please note that this home is professionally maintained including the grounds, therefore cleaning fees and additional costs for pets or extra guests are required so that we can keep things clean and well organized for our guests. If an unauthorized pet is brought to the property (if you bring a pet but didn’t add to your booking), you will be charged a fee of $200.

The home includes many amenities in addition to the lake access. Please review the list so that you don’t bring something we already have! Some that are not listed include paddleboards, snow shoes, fishing poles, and yard games (corn hole, kan jam, and bucket golf).

In the event you book for longer than 45 days, we may request a lease agreement. This is simply to assure we are on the same page with the requirements outlined within this listing. Don’t worry, it’s very straightforward!

Please note that the house sleeps 8 which includes the use of an air mattress that we provide. If there are 8 people planned for your stay, please let us know and we will be sure to have the air mattress setup for you in the event you’d like us to do so!

*RULES*

- Guests are responsible for any and all broken or damaged items.
- No alterations to the interior or exterior of the home of any kind are allowed without written permission from the property owner.
- This is a respectful neighborhood and a safe lake-life community, please be respectful of the people around you including avoiding disturbance of adjacent properties and neighbors.
- No one under the age of 18 is allowed to stay in the home without responsible adult supervision.
- Gatherings are allowed, but parties, including those that involve irresponsible drinking, lack of adult supervision, and/or destructive behavior are prohibited and may result in fines, if applicable. Please be respectful of this beautiful home!
- Access to the basement area (other than laundry room) is prohibited. This is mechanical space and is only to be accessed by property management. Access to this area is monitored via alarm door contacts, so please be aware that an alarm will sound upon entry.

Amenities:

Cleaning products • Hair dryer • Shower gel • Free washer – In unit • Lake view • Body soap • Shampoo • Conditioner • Hot water • Bathtub

Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!
House
Hinsdale

Treat your family to the ultimate getaway in the Berkshires at this beautiful vacation rental on Lake Ashmere! The 3-bedroom, 4.5-bath home has ample amenities to keep everyone entertained, including a canoe, 2 kayaks, a fire pit, a ping-pong table, and 2 Smart TVs. Enjoy a relaxing afternoon on the water, or drive around and visit top attractions — Tanglewood is 19 miles away, and MASS MoCA is 21 miles away! In the evening, share dinner on the deck and admire the incredible sunset view.

The space
C0495241320 | Ping-Pong Table | Canoe & 2 Kayaks | Sunset View

Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: 2 Twin XL Beds | Upstairs Living Room: Full Sleeper Sofa

OUTDOOR LIVING: Private dock (no boats) w/ lake access, deck, patio, dining area, electric grill, fire pit (starter wood provided), private yard
INDOOR LIVING: Smart TVs, dining table, board games, laptop-friendly workspace
KITCHEN: Stove/oven, refrigerator, microwave, cooking basics, dishware & flatware, Keurig & coffee pods, blender, toaster, spices, trash bags & paper towels
GENERAL: Free WiFi, mini-split A/C & heating, complimentary toiletries, linens & towels, in-home laundry, laundry detergent, life vests, hair dryer, hangers
FAQ: Doorbell camera (facing front entry), quiet hours (10:00 PM-8:00 AM)
ACCESSIBILITY: 3-story home, 4 steps for entry, bedroom & 1.5 bathrooms on main level
PARKING: Driveway (3 vehicles), across the street (1 vehicle), no street parking

Guest access
Guests will have access to the entire property via self check-in

Other things to note
- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Must be at least 25 years old to book
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: This 3-story home requires 4 steps for entry. While there is a bedroom and 1.5 bathrooms on the main floor, interior stairs are required to access the lower-level bathroom and the upper-level bedrooms and bathrooms
- NOTE: Your safety matters. This property features a doorbell camera on the front door facing the exterior entry. The camera does not look into any interior spaces. The camera actively records video and sound when motion is detected
- NOTE: Please observe quiet hours from 10:00 PM to 8:00 AM
- NOTE: Boats are not allowed on the private dock

Hinsdale Landmarks on the Map

Compare the Best Landmarks in Hinsdale – Addresses, Prices, Stars, Rating, and Review Count

Property Name Address Price ($) Star Rating Review Count Book
Autumn Hill Lakehouse Hinsdale, MA, USA 385 4.0 10.0 1 Click here
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton Dalton, Massachusetts, USA 180 2.0 10.0 14 Click here
Picturesque Cottage with Sunroom on Ashmere Lake! Hinsdale, MA, USA 491 4.0 1 Click here
Lakefront Hinsdale Home ~ 10 Mi to Pittsfield! Hinsdale, Massachusetts, USA 512 2.0 10.0 2 Click here
Pittsfield Home with Deck - 12 Mi to Jiminy Peak! Pittsfield, MA, USA 370 3.0 9.0 1 Click here
Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences Peru, Massachusetts, USA 264 10.0 177 Click here
Lakefront Hinsdale Home about 10 Mi to Pittsfield! Hinsdale, MA, USA 596 3.0 1 Click here
Remote and Relaxing Cabin in the Berkshires Peru, Massachusetts, USA 225 10.0 90 Click here
Bershire Home Rental: Enjoy Berkshire Fall Foliage Washington, Massachusetts, USA 281 9.8 80 Click here
Quiet Lake house with beautiful water views Hinsdale, Massachusetts, USA 279 9.2 76 Click here
Berkshire Lake access Hinsdale, Massachusetts, USA 245 10.0 60 Click here
Ashmere Lake Log Cabin with privacy/2 Bedrooms/3 night minimum Hinsdale, Massachusetts, USA 242 9.8 59 Click here
Brooksong, the perfect Berkshires getaway Dalton, Massachusetts, USA 474 10.0 45 Click here
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere Hinsdale, Massachusetts, USA 362 9.8 33 Click here
Private Lake House in the Berkshires Hinsdale, Massachusetts, USA 307 9.8 24 Click here
Gorgeous Lake Ashmere Home with Private Hot Tub & Lake Views, Screened Porch Hinsdale, Massachusetts, USA 438 10.0 22 Click here
Ashmere Lakefront Apartment Hinsdale, Massachusetts, USA 177 10.0 20 Click here
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. Hinsdale, Massachusetts, USA 191 9.8 19 Click here
Berkshires Log Cabin by Evergreen Home Washington, Massachusetts, USA 329 10.0 8 Click here
Hummingbird Haven is a Berkshires Retreat surrounded by Nature and Local Charm. Hinsdale, Massachusetts, USA 329 10.0 5 Click here
Centrally located in the Berkshires - Cozy Bungalow in SE Pittsfield! Pittsfield, Massachusetts, USA 213 10.0 4 Click here
Pittsfield Home w/Deck - 12 Mi to Jiminy Peak! Pittsfield, Massachusetts, USA 283 9.0 4 Click here
Family-Centric Berkshire Getaway by Evergreen Home Pittsfield, Massachusetts, USA 537 10.0 4 Click here
Waterfront Ashmere Lake House Near Berkshire Attractions Hinsdale, Massachusetts, USA 769 10.0 3 Click here
Getaway w/Game Room & Theatre Pittsfield, Massachusetts, USA 316 10.0 2 Click here
The Perfect Escape; Log Cabin situated on 40 Secluded Acres of Wilderness Peru, Massachusetts, USA 185 1 Click here
Berkshire Cabin by Lake Ashmere Hinsdale, Massachusetts, USA 215 1 Click here
Beautiful Renovated Home, Close to Multiple Ski Mountains. Hinsdale, Massachusetts, USA 339 1 Click here
Large open floor plan. Private yet close to everything. Lovely meadow views Pittsfield, Massachusetts, USA 825 1 Click here
Lakeside Getaway Hinsdale 145 9.84 1 Click here
Berkshire sunset lakefront Hinsdale 170 1 Click here
Beautiful 2-BR + Loft w/ Hot Tub at Lake Ashmere Hinsdale 175 9.84 1 Click here
Relaxing Berkshire cabin on Lake Ashmere Hinsdale 200 9.9 1 Click here
Lakeside Serenity! Hinsdale 285 10.0 1 Click here
Autumn Hill Lakehouse Hinsdale 356 9.6 1 Click here
Modern Lakehouse with Private Lake Access Hinsdale 380 10.0 1 Click here
Lakefront Hinsdale Home ~ 10 Mi to Pittsfield! Hinsdale 638 10.0 1 Click here

Note: The prices for each Landmarks in Hinsdale do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here) to get the latest prices.

Frequently Asked Questions

Accommodations in Hinsdale that offer a pool include:

  • Bershire Home Rental: Enjoy Berkshire Fall Foliage.- Review Count: 80, Rating: 9.8
  • The Perfect Escape; Log Cabin situated on 40 Secluded Acres of Wilderness.- Review Count: 0, Rating: 0.0

Accommodations in Hinsdale offering spa or wellness facilities include:

  • Autumn Hill Lakehouse.- Review Count: 1, Rating: 10.0
  • The Perfect Escape; Log Cabin situated on 40 Secluded Acres of Wilderness.- Review Count: 0, Rating: 0.0

Family-friendly accommodations in Hinsdale include:

  • Autumn Hill Lakehouse.- Review Count: 1, Rating: 10.0
  • Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton.- Review Count: 14, Rating: 10.0
  • Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!.- Review Count: 2, Rating: 10.0

Pet-friendly accommodations in Hinsdale include:

  • Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton.- Review Count: 14, Rating: 10.0
  • Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences.- Review Count: 177, Rating: 10.0
  • Bershire Home Rental: Enjoy Berkshire Fall Foliage.- Review Count: 80, Rating: 9.8

Accommodations in Hinsdale that offer on-site parking include:

  • Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton.- Review Count: 14, Rating: 10.0
  • Picturesque Cottage with Sunroom on Ashmere Lake!.- Review Count: 0, Rating: 0.0
  • Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!.- Review Count: 2, Rating: 10.0

Some of the best Accommodations in Hinsdale are:

  • Autumn Hill Lakehouse.- Review Count: 1, Rating: 10.0
  • Picturesque Cottage with Sunroom on Ashmere Lake!.- Review Count: 0, Rating: 0.0
  • Pittsfield Home with Deck - 12 Mi to Jiminy Peak!.- Review Count: 1, Rating: 9.0

Some of the popular Accommodations in Hinsdale are:

  • Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences.- Review Count: 177, Rating: 10.0
  • Remote and Relaxing Cabin in the Berkshires.- Review Count: 90, Rating: 10.0
  • Bershire Home Rental: Enjoy Berkshire Fall Foliage.- Review Count: 80, Rating: 9.8