Best Accommodations in Hinsdale

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.

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

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!

- "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! 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.

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

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

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

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.

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

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.

- "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! 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.

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

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.

- "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."

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.

- "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."

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.

- "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!"

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.

- "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."

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.

- "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!"

*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.

- "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!"

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

- "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!"

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.

- "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."

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.

- "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."

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.

- "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."

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,

- "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."

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.

- "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 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.

- "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! "