Best Accommodations in Egremont

Berkshire Vacation Rentals: High End Berkshires Getaway offers accommodations in East Hillsdale, 16 miles from Norman Rockwell Museum and 20 miles from Cranwell Spa & Golf Club. This vacation home features air-conditioned accommodations with a patio. Tanglewood Musical Center is 21 miles away and Tanglewood is 21 miles from the vacation home. With free Wifi, this 4-bedroom vacation home offers a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are featured in the vacation home. The accommodation has a fireplace. Great Falls is 15 miles from the vacation home, while Canaan Village Historic District is 15 miles away. Bradley International Airport is 54 miles from the property.

Fireplace/Heating • Pet Friendly • Parking • Internet • Security/Safety • Air Conditioner

While you're here, you can enjoy all the comforts of home and more, including a seasonal outdoor pool and free WiFi, as well as air conditioning and laundry facilities. Other amenities include premium bedding, a memory foam bed, towels, and luggage storage.

Wellness Facilities • Security/Safety • Bedding/Linens • Internet • Air Conditioner • Toiletries • Guest Services • Pool • Fireplace/Heating • Other • Laundry • Parking

Berkshire Vacation Rentals: Private Estate Heated YEARROUND Outdoor Pool offers accommodations in North Egremont, 12 miles from Norman Rockwell Museum and 16 miles from Tanglewood Musical Center. Both free Wifi and parking on-site are available at the vacation home free of charge. The vacation home also offers an outdoor swimming pool and a garden for guests to relax in. Berkshire Vacation Rentals: Private Estate Heated YEARROUND Outdoor Pool features 7 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 5 bathrooms with a hair dryer. Towels and bed linen are provided in the vacation home. For added privacy, the accommodation features a private entrance. Tanglewood is 17 miles from the accommodation, while Cranwell Spa & Golf Club is 19 miles away. Albany International Airport is 50 miles from the property.

Air Conditioner • Security/Safety • Pool • Pet Friendly • View • Fireplace/Heating • Parking • Internet • Ev Charge Station

Welcome to our home in the village of Egremont (part of Great Barrington). Both the house and property are open and inviting! You'll feel relaxed the minute you arrive. The kitchen is equipped with everything you should need for your stay.

This home is just outside of downtown Great Barrington! Close to hiking, biking, shopping, skiing and the arts! We are in a perfect location for you to discover all the Berkshires has to offer.

You will have access to the entire home (and yard) during your stay. The semi-finished basement includes a ping pong table (although carpeted, it is a basement so we recommend shoes down there). There is wood for the fireplace in the garage.

My family and I live in CT, about an hour and 20 mins away. We can provide feedback on what to do in the area or answer any questions about the house. Please let us know if there is anything we can do to make your stay more enjoyable!

Sleeps 8 on beds, but air mattress is available for 2 extra guests.

Dogs occasionally visit the property with guests (we can accommodate pets for an additional $25 cleaning fee and $100 deposit)

- "This property was comfortable and relaxing for . The 2 couples. Shyirah provided every necessity and the property was very nice and organized. She is an excellent communicator and texted us before during and after our stay to make sure everything was in order. Egremont is a quaint, quiet town Close to Great Barrington, Lennox, and other towns in the Berkshires. We visited the nearby shops and took a nice walk along the river in Bish Bash park to see the waterfalls.. And over all great 2 nights."

Near Hiking Renovated 4-Acre Berkshires Retreat! is located in South Egremont, just 18 miles from Cranwell Spa & Golf Club and 18 miles from Tanglewood Musical Center. The air-conditioned accommodation is 13 miles from Norman Rockwell Museum. Tanglewood is 18 miles from the vacation home and Great Falls is 12 miles away. With free Wifi, this 3-bedroom vacation home provides a flat-screen TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are provided in the vacation home. The accommodation has a fireplace. Canaan Village Historic District is 12 miles from the vacation home, while Holley Williams House Museum is 14 miles away. Bradley International Airport is 51 miles from the property.

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

Child Friendly • Bedding/Linens • Kitchen • Balcony/Terrace

Summary:
Gather your friends and family at this a luxurious 5-BR retreat. Nestled in the serene woodlands of the Berkshires, this home features five bedrooms, four full bathrooms, a spacious living room with fireplace, a fully equipped kitchen, and ample space for everyone. Enjoy the hot tub, sauna, and indoor pool for ultimate relaxation. The outdoor deck, complete with a grill, is perfect for entertaining and dining al fresco. Experience comfort and tranquility in this beautiful woodland retreat.

The Space:
Private 5-BR house located in Egremont.

Things to do:

- French Park - 9-min drive.
- Catamount Mountain - 9-min drive.
- Prospect Lake - 11-min drive.
- Great Barrington - 13-min drive.

Guest Access:
Accessible with a smart lock.

The Neighborhood:
Located in Egremont 9-min to French Park, 9-min to skiing at Catamount, 11-min to Prospect Lake, 13-min to Great Barrington.

Getting Around:
Vehicle is recommended, with 4x4 or AWD in the winter. Ride shares may be unreliable.

Other Things to Note:
Notes & Disclaimers:

Pool and Hot Tub Covers: To ensure safety and maintain the quality of our amenities, please make sure that the pool and hot tub covers are closed whenever they are not actively in use.

Wildlife: This is a home in a rural part of the country. You may see wildlife including deer, coyotes, foxes, and bears. Please be mindful of your surroundings and leaving out food and trash.

Weather: In the winter, there will be snow, ice, and occasional snowstorms. We recommend driving a vehicle with AWD or 4WD. Please drive with caution and be prepared with regards to the ability of your vehicle to drive in the snow.

Power & Internet: This is a rural part of the country. You may lose power or internet during inclement weather. We do not issue refunds for loss of power or internet out of our control.

AC availability is seasonal and depending on weather (late spring and summer). Heating is also seasonal, and depending on weather, available during the cold seasons (autumn-winter).

Pets: We’re happy to welcome your pup to the home. There’s a $150 fee plus tax for the first dog, and $50 plus tax for each additional one. If you’re planning to bring more than three, just check in with us first so we can coordinate with the homeowner. For everyone’s comfort, we kindly ask that dogs stay leashed outdoors and that you clean up after them. Please note that cats aren’t permitted due to allergy concerns. Any pet-related damages may result in additional charges.

Cancellation Policy: We cannot make any exceptions to our cancellation policy. Please consider traveler’s insurance.

Interaction with Guests:
No interaction with host required; available on chat service.

- "We just spent an amazing long weekend with my family and my sister's family. The house itself is in a private wooded area but close to Great Barrington. While the pictures of the house listing are beautiful it is even more spectacular in person with a large open living room and functioning fire place. The kids occupied themselves playing pool and foosball, playing outside and swimming in the heated indoor pool. There were rafts and masks available for use. The adult enjoyed relaxing in the hot tub. The kitchen is a great space for cooking meals and gathering. The property managers got back to us quickly when we reached out with a couple of questions. The beds were super comfortable and the views from the endless decks were fantastic especially at this time of year. Our only regret was not staying longer! It is a little pricey, but I would say worth every penny! The kids are already asking to come back. "

Welcome to Moose Lodge – A 7,500 Sq. Ft. Berkshires Luxury Retreat

Experience the pinnacle of comfort and entertainment at Moose Lodge, a stunning 7,500 sq. ft. retreat nestled in the heart of the Berkshires. Perfect for gathering with friends and family, this expansive property offers an abundance of space, luxurious amenities, and a secluded location while keeping you close to vibrant local communities and attractions.

Why You’ll Love Moose Lodge:
Expansive Living Space: Spread out and relax in 7,500 sq. ft. of thoughtfully designed interiors, perfect for both quiet moments and lively gatherings.
Fully Appointed Outdoor Cooking Area: A chef’s dream with everything you need to prepare and enjoy meals al fresco.
Entertainment for Everyone:
Home Theater: A state-of-the-art space for cozy movie nights.
Game Room: Enjoy a billiards table, foosball, poker table, and blackjack table—perfect for hours of fun and friendly competition.
Luxurious Bedrooms: Rest and recharge in plush, comfortable accommodations with serene views.
Outdoor Bliss: Relax on the spacious patio, take in the fresh air, and enjoy evenings by the fire pit under the stars.
The Perfect Berkshires Location:
Nature’s Playground: Explore nearby hiking trails, lakes, and scenic drives, all just steps away from Moose Lodge.
Cultural Gems: Minutes from charming towns with farm-to-table dining, boutique shops, and iconic attractions like Tanglewood and the Norman Rockwell Museum.
With its sprawling 7,500 sq. ft. layout, Moose Lodge is ideal for creating unforgettable memories. Whether you’re enjoying a movie in the theater, competing in the game room, or dining under the stars, this luxurious retreat has everything you need for the perfect escape.

Book your stay at Moose Lodge today and let the adventure begin!

- "We had a wonderful stay at Moose lodge. We had a family wedding and this just made our weekend even better. We love the house and we love Wendy!!!" - "This was the perfect stay for our work retreat!!! Wendy took care of everything - tons of communication, literally everything you need to entertain / cook / hang out. The amenities are stunning - the theater and game room was a highlight for the 15 of us. And the Moose theme is so cool! Couldn’t recommend enough :)"

Situated on 26 acres in the heart of the Berkshires in the small town of South Egremont, MA, this early 19th c. house combines the charm of the antique with all the modern conveniences including two screened-in porches. Conveniently located five minutes from Gt. Barrington, MA and 25 minutes from Stockbridge, Tanglewood, and Hudson, NY. The property also sits adjacent to the Appalachian Trail with plenty of local options for hiking and skiing. We are central to the many cultural attractions that make the Berkshires such a year-round attraction.

A three bedroom home, the first floor contains a living room with fireplace, exposed beams and overhead fan, a modern kitchen, sitting room with fireplace, master suite, bathroom, laundry/dressing room, and two screened-in porches. The second floor consists of two bedrooms, and an additional full bath. Central air conditioning throughout with additional auxiliary window air conditioner in one upstairs bedroom, ceiling fan in living room. Barbecue grill as well. Guests have the whole house to themselves.

Guests have access to the whole house. Additional amenities include: full kitchen, Wireless Internet, TV, heating/air conditioning, washer/dryer, indoor fireplace.

- "We loved it: the converted house was lovingly restored and updated. Elegant, with all the New England farmhouse hallmarks (wide plank floors, six-over-six windows, original winter and summer kitchen fireplaces, large latched doors, and a winding staircase) updated with two full bathrooms and a large eat-in kitchen. Close to everything we wanted to be close to. We will definitely try to stay here again!" - "A lovely home in a beautiful bucolic setting. It's everything one could want for a peaceful getaway in the Berkshires. Perfect location to be both in a quiet setting yet near cultural center. Just wonderful!"

The Freeman Berkshires sits on 40 acres of manicured landscape with a tennis court, a four-acre vineyard, a myriad of amenities and rolling views of a large pond on property and Mount Everett beyond. Whether you want to relax in the library, cuddle up in the lodge room, enjoy the artist's loft or snuggle up in front of one of the home's six fireplaces, you will find beautiful spaces to enjoy in groups or in solitude. 100% carbon neutral.

The property offers two dining rooms (including a fifteen foot custom dining table), a well equipped kitchen, herb and vegetable garden, fire pit and expansive multi-level blue stone patios and decks. A three car garage and loft is included.

We provide a long list of amenities, including a paddle board, four person metal row boat and kayak for the pond. For the kids big and small we offer a retro arcade, foosball table, ping-pong, board games, PS4 and a virtual reality gaming system. For outdoors you will find bocce, croquet, tennis and badminton equipment, large Jenga and more.
The Freeman Berkshires is an innovative social equity vehicle. Owned by 141 investors from Main Street and Wall Street through Shared Estates' equity crowdfunding model, the property is part of a transformation that levels the real estate investing playing field.
The Berkshires is one of the country's top cultural centers: Massachusetts Museum of Contemporary Art (largest in the US), Kripalu (largest yoga center), Williams College (#1 Liberal Arts College in the US), Tanglewood, Shakespeare and Company, The Mount, Clark Art, Jacobs Pillow and more.
The Berkshires is also home to a variety of outdoor destinations: Bousquet, Butternut, Catamount (longest zip line in the USA) and Jiminy Peak.
One 90" TV in the lodge room for family movie nights. We provide the popcorn, biscotti, teas, cocoa, candy and more. A welcome basket of local goods and fresh cut flowers greet your party.
The Freeman Berkshires is named after local Elizabeth (Mumbet) Freeman - the first African American to sue and win her freedom under the Massachusetts constitution in 1781. You will find a variety of sculpture and original art installed in tribute to her story. The property donates 1% of net income to the Elizabeth Freeman Center, a 501c(3) that works to end cycles of domestic violence.
Owner's previous property was #1 on VRBO in the Berkshires, and was showcased on Netflix's "World's Most Amazing Vacation Rentals" series.

- "We really enjoyed our stay. The place was beautiful and expansive. It was large enough to create privacy amongst multiple families. Really enjoyed all the different living areas. Highly recommend." - "This was our second year for a family gathering. We love the privacy, the art, having our own pond! And the Black history that is highlighted Property manager responded to a few small issues promptly. It is a gorgeous and elegant place to vacation and t relax with lots of access to hiking, biking and the arts Thanks"

*pool and hot tub closed for 2025, will reopen March 30, 2026*

In one of the most sought after destinations in New England, located just outside Great Barrington near the top of Baldwin Hill where the mountains ring your view in every direction, sits a secluded three bedroom home with heated pool, hot tub, sauna, wood firepit, pickleball court, separate Clubhouse, and extensive gardens. Home has a master bedroom suite located on the first floor with adjustable Queen bed with an expansive two-room bath with walk-in shower and beautiful soaking tub surrounded by marble-- and your hot tub and sauna are right outside via your private door. This room is equipped with its own Asko washer and dryer. Upstairs, find two bedrooms (one with adjustable King bed and one with two Twins) and a large living room full of windows overlooking the forest. Living room has extra large flat screen TV and a gas fireplace, along with full bar area with beverage cooler, dishwasher and icemaker. Daybed with with real twin-sized mattress for overnight guest is super comfy when cuddling in for movie night! Fully modern kitchen with gas range and Perlick fridge, freezer drawers and icemaker stretches seamlessly into the family area where you will find a wood burning fireplace surrounded by windows with views of the professionally maintained lawns, gardens, and pool. Extra large round dining table seats 10+ people in comfortable upholstered chairs! All bedrooms have remote controlled exterior privacy shades on all windows. In a separate building, the Clubhouse is designed for gathering with its loft office/teen/gaming area stocked with Switch that's loaded with games, Queen sleep sofa, full bathroom, gas fireplace, kitchenette, ping pong table, and beautiful deck with second gas fireplace for warmth on those chilly evenings, overlooking the woods. House and Clubhouse are modern and filled with light. Both were built/renovated within the last few years. Bonus Pink House with porch swing is heated and has a full fridge and a large sink -- it's the perfect spot from which to serve drinks and al fresco meals to your guests! Propane bbq for grilling near the lounge area by the pool, and on the other side of the pool is a screened in porch for dining bug free or relaxing in the shade. After a pickleball match, you'll want to take a swim in the heated pool, or head straight to the hot tub or sauna! Or just enjoy a hot shower in the private outdoor shower area. Take a long walk to the back of the 18 acre property via wide full driveway, or do as the locals do and walk to the top of Baldwin Hill. A huge expanse of the rear yard is fully fenced for your pet. In addition, there is a small pet run accessed through the one car garage, where you will also find a pet washing station and the second washer and dryer. We have both Tesla and generic car chargers installed for your convenience. Located in the quiet hamlet of Egremont, MA just minutes away from everything the Berkshires has to offer! Catamount Mountain Resort 5 minutes; Lenox, MA and Tanglewood 30 minutes; Stockbridge, MA 25 minutes; Hudson, NY 30 minutes; Chatham, NY 25 minutes; Butternut Ski Resort 20 minutes, Monument Mountain 20 minutes. We provide everything you need for your stay including high quality organic linens (our mattresses are all organic too), fully stocked kitchen (including fresh spices, oils and vinegars), toiletries, pool towels, and firewood. Lightning -fast fiber optic internet with separate modems for house and Clubhouse ensures you are never offline. Whole house generator covers both buildings, so you won't be affected if the local power fails! Parking for 8+ vehicles. We pride ourselves on the cleanliness of our home. Allergy sufferers will appreciate the bare teak floors and lack of curtains, along with regular steam cleaning of upholstery. Our cleaning team uses only non-toxic and natural cleansers and our linens are free from softeners or fragrances. Air ducts, windows and exterior are cleaned twice per year, and we are happy to come by to correct any variance from a sparkling clean and comfortable home for your stay! With our local management team, we are always around the corner to assist you with whatever needs may arise. We also offer additional services such as full cleaning, daily freshening, grocery delivery, or whatever else you may need. Pamper yourself on your next visit to the Berkshires!

Please note: Pool is closed for the 2024 season. Pool will be open April 30 - Septmeber 30 in 2025. Hot tub and sauna are open year round.

Need less space? Visit our VRBO listing Baldwin Hill Retreat Guest House #40334149. Need more space? Visit our listing that combines both, Baldwin Hill Compound #4090753

- "This is a wonderful location in the Berkshires - close to activities and hiking, Great Barrington, and shopping. Communication about the house was easy and the host is very responsive. The grounds of the house are beautiful - we spent most of our time outside. It was great to have a washer/dryer and the kitchen is well-stocked. Thanks!" - "This property was perfect for our annual family vacation, grandparents and two families with kids. Everyone had enough space and privacy while also feeling close and able to socialize. House was well stocked with everything we could need, from towels and extra sheets to board games and books. Outside property was perfect, lots of space to play, swim, eat and relax. Location was close to town and easy to go out to eat or grab some groceries. We had a great stay and would return every summer if we could! "

Experience the breathtaking views of Mt. Everett from one of the oldest homes in the Berkshires. Our meticulously maintained 1740s homestead maintains many of its original features and is a perfect place for those looking for a quiet and private place to relax and recharge.

Location:
Minutes to local ski areas, downtown Great Barrington, Salisbury CT and many more attractions such as Tanglewood, Jacobs Pillow, Shakespeare and Company, Lime Rock Park, Berkshire School, and more.

Space:
Cozy up next to one of the many fireplaces and unwind with your favorite read. Don't worry if you forgot your book, our bookshelves are stocked with a variety of interesting reads both fact and fiction. The two large fireplaces located in the formal dining and living room are a magical feature of the home. They create the perfect atmosphere for celebrating a special occasion or holiday. An addition to the original house features a bright kitchen/family room space with modern appliances and beautiful custom cherry countertops that will keep the cook in your family happy. There is also a wood-burning stove in this space which makes it an inviting place to connect and relax during those cool fall and winter days. Our house also features a greenhouse space which is active from mid-fall through to the spring. Guests are welcome to interact with and enjoy the space.

Outdoor Space:
Our 10-acre property is surrounded by conservation land with several walking trails accessible directly from the property. Your morning coffee will feel extra satisfying while sitting on the terrace overlooking the perennial garden and backyard pond. Throughout the year a diverse population of waterfowl stop at the pond for a little rest during their own travels. We have a large gas grill for all your barbecuing activities.

Other things to note about our property:
+ The house is nearly 280 years old and retains its original construction. There is air conditioning in 2 bedrooms and the kitchen area only.
+ We currently are not allowing any parties or events at the home.
+ It is our experience that the house can feel cramped with more than 6 adults. We allow up to 6 adults. Max guest of 8, which would include any children.
+ NO PETS
+ NO SMOKING in our property
+ Picnic supplies/chairs/blankets etc are available for guests attending local outdoor venues.
+ The barn on the property is not for the use of guests.

- "I've been visiting the Berkshires for years and I can say that this stay was my absolute favorite. This beautifully maintained home takes you back to the late 1700's early 1800's where one can visualize the way people used to live with the wide board wood floors and multiple fireplaces. Updated and spacious it is a pleasure to spend time within. The location is perfect. Enjoy morning coffee while admiring the vast and beautiful grounds. Very secluded, peaceful and private. Yet minutes away from downtown Great Barrington. The beds were incredibly comfortable and house was very clean. We cannot wait to return!"

Cozy house conveniently located in a quiet area near the village of South Egremont. Fresh air, natures beauty all together close to Great Barrington and 2 ski resorts. This house is close to one of the most beautiful parts of the Appalachian Trail as it travels through the Berkshires. Nearby are beautiful lakes, mountain views and waterfalls. There are amazing country roads with spectacular colors in autumn.
The house contains the basics and has a spacious modern kitchen. Relax in the cozy den or the rustic living room. Even with its convenient location, it is quiet, and has been known to have a variety of wildlife around the yard.

- "Close to everything, skiing, ropes courses, ponds, shops. You need a car but otherwise house has all you need. David and Yasmin respond very quickly!" - "David and Yasmin were easy to communicate with and had great recommendations for the area. We had 5 adults in town for a show at Tanglewood and we all (plus a dog!) found the house plenty roomy and comfortable. Area was buggy but we brought our own citronella candles and sitting outside was very pleasant - the sky was so clear and full of stars our first night! Perfect accommodations and location for our trip."

Summary:
Awaiting your next trip in our former horse farm turned luxury vacation rental, recently upgraded and re-furnished.

Discerning guests will be impressed with the estate's grounds, including a brook that runs through the property and an abundance of wildlife. Known to many locals as the most beautiful property in the area.

The Space:
Two living rooms, a dining room, a screened-in porch, multiple Goshen-stone patios, and many beautiful acres—a truly memorable property with endless lovely nooks and crannies.

Now with a brand-new 8x20 pool, with endless jets, Goshen-stone surround, and beautiful views of the entire farm. The sunrise and sunset play over wide-open fields that cascade to the hundred-acre forest of maple, oak, birch, and pine trees below.

Large 5-bedroom house and 50 surrounding acres of field and woods.

Decorated in antique English farmhouse library style, the high end chef’s kitchen comes with Miele appliances, induction stove, small bakers oven and oversized Subzero refrigerator. Impress your guests with home-cooked meals, or ask us about recommendations on a guest chef for the night. Owned by art collectors, there is gorgeous art and antiques throughout the house.

There is room for 6-8 in the kitchen table as well as seating for 12-14 in the dining room. Gorgeous back patio under cantilevered garden beds with grill out the French doors from the dining room; huge front patio with decorator’s 15-piece patio furniture set
in the front. Truly this house was made for dinner parties!

There is both a living room and den on the first floor. The den has smart TV for streaming your devices. High-speed Wifi.

Sleeping:
Multiple spaces give you plenty of space to spread out and enjoy peaceful retreats each night:
-Primary bedroom on the first floor has a king size bed. En-suite master bathroom has a freestanding clawfoot tub and separate STEAM SHOWER.
-Second bedroom on the first floor combines sleeping space with office space; there are built-in shelves and a desk, as well as a full bathroom directly across the hall. The office bedroom has a queen size bed.
-Three bedrooms on the 2nd floor: one with two queen-size beds, the second with a queen-size bed and a sleeper couch, the third with one queen-size bed.

In-law apartment:
2 bedrooms with queen size beds

Couches in both living rooms are large enough for very comfortable sleeping as well. A folding cot in the master bedroom closet is available to add to any space.

Bathrooms:
-Four full and one half bath: two full bathrooms and one half-bath on the first level, one full on the second level. I bathroom in the in-law suite.

Outdoors:
Brand-new, stunningly landscaped 8x20 pool. Goshen-stone patio surround with a stone wall and quaint, safe farm-house fence. Pool serviced 2x week; Endless Swim Jets allow for amazing exercise as well as fun for the family.
There is a brook that goes through the property, with two bridges. There is abundant wildlife--frogs, birds, turtles, fish, deer, chipmunks, and many more species. There is a pond, visible from a lovely screened-in porch, patio, and pool. There is a peace sign mowed into the rolling hill above the pond, which has been maintained by many generations of owners. There is beautiful landscaping around the house, including many special spots to sit or play.

Other things to look forward to:
-Parking for 4-5 cars (or more)
-Central AC to keep you cool during the summer. Multiple heating zones for climate control in all seasons. Back-up generator in case of weather
-Brand new, large-volume washer/dryer
-Hardwood floors throughout with vintage area rugs
-Three steps to reach the back door so easily accessible for all
-Free swimming at Lake Mansfield and Lake Garfield a little bit further away.
-Free electrical vehicle charger available for use!

Guest Access:
Everything you need for a great stay—hotel-quality toiletries, linens, towels, hairdryer, iron and ironing board, washing machines, detergent, and more!

Other Things to Note:
-The pool waiver must be signed in order for us to provide access to the pool area. Please note that we make no assumptions during winter months below 32 degrees that pool will be warm enough to enjoy.
-The road to the house is steep and narrow, during the wintertime a 4 or all-wheel drive car is recommended.
-Bring your furry friends, two dogs are allowed. $50 per dog per stay. Dogs must be at least one year old, sorry no puppies!

If you are booking through VRBO: You agree that The Host will charge your card for the full payment of the stay 24 hours after booking. Any payments by VRBO (service fees) will be charged separately.

Damage: Your rental includes an accidental reported damage waiver fee up to a maximum of $800. The cost to repair any accidental and reported damage to the rented property including any missing or broken items up to a maximum of $800 will be covered at no charge to you as long the damage is reported to your Host before you depart. Pet damage, pool and hot tub damage are not covered in the accidental damage waiver.

- "House had everything a big group would need, including multiple indoor and outdoor spaces to spread out. Large property felt very secluded-most of our group didn’t leave all weekend." - "My family, ages 1-91, had a Hallmark perfect Christmas weekend. With 12 people everyone had enough space throughout the home but we were also comfortable gathering together in the kitchen, dining room and living areas. We greatly appreciated all of the wonderfully curated art “moments” throughout the home which were interesting and still inviting. The heated pool was fabulous, especially in the snow! We were very comfortable with our children in the home. Beds were wonderful and towels and linens were of high quality. The kitchen oven is small but we were able to cook a full Christmas roast between the kitchen oven and in-law oven. Hosts were very communicative. We are so grateful for this beautiful and inviting retreat and hope to book it again in the future!"

In the summer spend time on the large screened porch and decks. Great room has sliding doors leading to deck facing east surrounded by perennial garden. Natural light flows in through the three skylights above dining area. Master bedroom has a wall of glass and fireplace and the ensuite bath has skylights and glass all around.
Fitness room in basement with exercise bike, rowing machine, weights, TRX, ropes and more. If you play keyboard or guitar please use ours to keep up practice
We have John Andrews and the Old Mill Restaurant minutes away and The Barn (recently renovated performance space) offering dinner.
Ski closeby at Catamount or Butternut.

- "We visited for a week in August and had a great time. The house is located in a great spot close to all that Great Barrington has to offer, but also far enough out of town to feel away from it all. We really enjoyed the screened in porch and the fenced in garden." - "This rental in the Berkshires is beautiful. The master bedroom has an incredible master bath with a sunken Jacuzzi tub and a fireplace. It’s well located and close to Great Barrington with all the wonderful restaurants there. Close to beautiful hiking too."

Shingled farmhouse with modern interior. Spacious & sunny kitchen that connects to the large outdoor patio with fireplace, living room with flat screen TV, first floor guest bedroom, laundry and full bath with tub. The second floor master suite has cathedral ceilings with exposed antique beams, a dressing area and modern bath with shower. High speed internet.

The property is just around the corner from downtown South Egremont, less than 5 minutes into Great Barrington and Catamount Ski Resort.
Broker owned.

- "Thanks for a great stay. The home was updated, clean, and quiet. We appreciated having a full kitchen to cook in. The location was really convenient for all our summertime outdoor activities." - "We appreciated this small and carefully renovated house. The kitchen space is ample and handsome… a great place to hang out. The living room is snug and comfortable, and the bedrooms / bathrooms are very nice. Altogether pleasant and comfortable. We older folks found the stairs a little challenging, so do note if that’s an issue for you."

CATAMOUNT SKI RESORT IS SEVEN MINUTES AWAY. 11 MILES TO SKI BUTTERNUT.
HIGH SPEED FIBER OPTIC INTERNET

Our vacation home is built into a steep, secluded, forested mountainside, near the village of South Egremont. It is a short distance from all the wonderful attractions located in Berkshire County, as well as Columbia County in New York -the heart of the Hudson Valley (only 1 mile over the mountain), and Litchfield County, Connecticut (only a 10 mile drive). There is no light pollution, and other than the sounds of nature, it is so quiet at night you can hear the beating of your heart. The house has two large decks and a smaller side deck that provide great views of the surrounding countryside. The only likely neighborhood residents you will see (we have) include bear, deer, moose, fox, eagles, hawks, ravens, and numerous owls.
Timberdoodle is close to many of the attractions for which the Berkshires of Western Massachusetts are noted for. It is five minutes away from one of the best restaurants in Berkshire County-the Old Mill. Hiking, skiing and other outdoor recreation are within 10 minutes of our vacation home, including the Appalachian and South Taconic Trails, the Jug End State Reservation, and Bash Bish Falls-the State's highest. The picturesque town and local commercial hub of Great Barrington is only a 7 mile drive. The house is only 21 miles from the famous Tanglewood Music Center, the summer home of the Boston Symphony Orchestra. Nearby cultural venues abound, including Jacob's Pillow Dance Center, Shakespeare & Company, the Mahaiwe Performing Arts Center, and the Colonial Theater.
The kitchen, although compact, has all the appliances and equipment necessary to make fantastic meals from the locally raised and grown food that you can obtain at the many farmer's markets in the area. All essentials are included, such as towels, bed sheets, soap, toilet paper and pillows. There are fully stocked pantry shelves including coffee beans, essential kitchen staples, condiments and dry goods. The kitchen includes a Kitchen Aid ceramic top convection range, Bosch dishwasher and Fisher Paykel french door refrigerator/freezer. The kitchen inventory includes a Breville toaster, Panasonic combination microwave, steamer and convection oven, Vorwerk Thermomix (a German blender on steroids), an Instant Pot, Cuisinart food processor, Baratza Coffee Grinder, and a Technivorm drip coffee maker. The kitchen has been provisioned with fine kitchenware including from Cristel, Le Crueset, Mauviel, Finex, Wusthof and ScanPan. The upper deck contains a gas grill, and a Blaze Kamado-style charcoal grill is located in front of the house near the lower deck. For in-home entertainment, the living room has a 4K high definition television connected to a Dish satellite receiver. Both this television and the one located in the large top-floor bedroom are connected to internet streaming services provided by Roku boxes. We have no air conditioners. Because of the cool mountain air and the 1300 feet elevation, we only occasionally use the provided fans on the hottest Summer days.
Two of the bedrooms have queen beds and the third bedroom has two twin beds.

A SUBSTANTIAL DISCOUNT IS AVAILABLE FOR SEASONAL RENTALS

- "This was our second season at Timberdoodle. A wonderful home tucked into the mountainside in Egremont. The host was very easy to deal with and very accommodating to our change in plans. We will be returning next year." - "We had a lovely post-holiday season family vacation at Timberdoodle. Plenty of space for all of us to relax. We loved the quiet mountainside location. A dusting of snow confirmed our only visitors were some bears passing through the property. The view from the house is amazing. The efficient kitchen made it easy prepare all the meals we wanted to cook. When we tired of making meals we found many wonderful dining options a short drive away. In addition to dining - shopping, skiing and hiking options abound. Perhaps the best feature of the home for wintertime was the wood burning fireplace insert. Excellent!"

10 MINUTES TO CATAMOUNT
Ski, hike, shop, and dine with this beautiful 2-bed, 1-bath Berkshires cottage as your home base. 7 minutes to downtown Great Barrington, this stylish, cozy rental has everything you need for a great getaway. A new renovation brings modern amenities to this classic 50’s cottage. Enjoy a chef’s kitchen, 500 sq-foot deck with hot tub, and thoughtful touches like yoga mats, a record player, board games, and a backyard hammock.

Monthly ski rental discounts are available!

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 in a centralized Berkshires location with a private property featuring peaceful forest views.

Front door security camera (1, facing driveway), 2 small steps required for home access

The open floor plan of this one story cottage lets in the perfect amount of natural light to enjoy the stylish space. The spacious galley kitchen will all new appliances is stocked with everything you need for meals at home. The dining area looks in on the cozy living room equipped with many streaming services to watch on the beautiful frame TV. A washer and dryer unit is available for guest use.

The two bedrooms both feature queen beds. There is a newly remodeled bathroom with a tiled walk in shower.

There are 3 window AC units in the summer months, 1 in each bedroom and 1 in the living room.

Cozy up for an evening around the outdoor fire pit, relax in the backyard hammock, or enjoy a meal on the spacious outdoor deck with a full dining set and BBQ. A partial privacy screen blocks the view of the hot tub from the street. Guests will walk through the garage to enter into the backyard.

Venture out for a day of winter activities. This cottage is located only 9 minutes from Catamount and 15 minutes from Butternut. Being only 7 minutes away, enjoy all that downtown Great Barrington has to offer.

Ideally suited for a romantic getaway with your sweetheart or a couple’s weekend escape, this updated cottage is the perfect retreat for some R&R in the Berkshires.

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

LOCATION: This house is in a centralized Berkshires location with a private property featuring peaceful forest views.
PETS:Small dogs allowed with owner approval, no dogs under 2 years old. Please reach out for owner approval on the dog prior to booking. No multiples. $100 fee will be applied if approved.
PARKING: Free Off street parking for up to 3 cars in the driveway, no parking in garage
HOT TUB: Please keep the hot tub closed when not in use. Make sure the jets are off before you close up. Be aware of the potential health risks associated with hot tubs before you use it, and use at your own risk.
*Free WiFi, washer/dryer, towels/linens, complimentary toiletries
*This home is not baby and toddler proof.
*Netflix, HBO max. Peacock, Spectrum cable (NYC), Hulu, Disney +, and Discovery + are all available, we just ask that guests watch under the guest profiles.

**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.

- "Clean, comfortable, convenient" - "The property was perfect for a long weekend getaway. The house was very clean with updated appliances and comfortable beds. Easy drive to Great Barrington shops and Catamount. The host checked in with us and was accessible." - "Nicely renovated cottage in the Berkshires! Nearby to several Ski Resorts, so we skied at 3 places during our visit! We really enjoyed our stay! Thank You!" - "We had a wonderful week long stay at the cottage this July. It was super clean, quiet, and had everything we needed for a wonderful stay. Easy to communicate with host. The guidebook had great tips and ideas. The local area had lots of hiking and swimming spots, lots of great food too. Hope to come back next summer!"

Summary:
Expertly renovated four bedroom house with views of Catamount, post and beam wood ceilings and a lovely centerpiece fireplace. High ceilings, renovated kitchen, perfect outdoor space and under a mile to Catamount Mountain for skiing in the winter and zip lining during the summer. Located on a private road with several restaurants within a five minute drive and only eleven minutes to downtown Great Barrington. Bring your family and your furry friends too and enjoy!

The Space:
The recently renovated chef’s kitchen has white shaker style cabinets, butcher block counters, stainless steel appliances and gas cooking. Well stocked kitchen with all the necessary cooking/serving items including cookware, pots, pans, plates, bowls, glasses, mugs and silverware. Coffee bar with both Cuisinart and Keurig ( pods supplied ). There is seating for up to eight at the dining table, plenty of space for all to enjoy home cooked meals!

The living room is just past the kitchen and has a large stone wood burning fireplace as its centerpiece. There is a comfortable sectional sofa with a Smart TV with streaming capabilities. You can log into your streaming apps on the TV such as Netflix, Hulu, Amazon Prime, etc. There’s also a second seating area with another couch and chair to sit and take in the mountain views.

In total, there are four (4) bedrooms to accommodate guests during your stay. The four bedrooms are all on the second level of the house, for easy planning, here are the bedroom layouts:
Bedroom 1: king size bed
Bedroom 2: queen size bed
Bedroom 3: full size bed
Bedroom 4: two twin beds

There are 2 full bathrooms in the house both recently renovated. One is on main level with shower and other one upstairs with tub/shower combo.

Outdoors is where you can truly experience the Berkshires. Outside you’ll find a brand new front porch and deck, gas grill, and plenty of seating in a totally private setting. New for 2023 is an firepit/conversation area with Adirondack chairs.

Other things to note:
-Central AC to keep the house cool during the summer.
-Three stairs to the front door and about fourteen stairs to the second floor where the bedrooms are.
-Hardwood floors throughout, tile in the bathroom and kitchen.
-Parking for 5 vehicles just to the left and rear of the house
-Washer/dryer for guests to use.
-Hotel quality linens and towels, as well as shampoo, conditioner and body wash all provided for our guests.
-Amenities for little ones including portable mini crib and baby bath.

Bring your furry friends, two dogs are allowed. $50 per dog per stay. Dogs must be at least one year old, sorry no puppies!

Guest Access:
The entire house is reserved for your enjoyment. If there is anything you need during your stay we are available via phone or your booking channel!

The Neighborhood:
Under 1 mile from Catamount mountain for winter skiing and summer ziplining.
1 - 5 minutes to fine restaurants like John Andrews Farmhouse and the Old Mill, casual breakfast/lunch spots like Mom's Cafe, or music and drinks at the Egremont Barn. '
5 - 7 minutes to several restaurants in nearby Hillsdale NY.
6 minutes to Prospect Lake ( bring your kayak or paddleboard , or jump in for a swim )
15 minutes to larger Copake Lake
12 minutes gets you to downtown Great Barrington for shopping, ice cream ( try Soco Creamery ), food shops, and more.

Short drive to many hikes including Bish Bash Falls, Monument Mountain, and some spots where you can pick up the Appalachian Trail.

Other Things to Note:
We look forward to welcoming you soon!
Standard rules like no smoking, no partying and being respectful of the neighbors apply.

-Bring your furry friends, two dogs are allowed. $50 per dog per stay. Dogs must be at least one year old, sorry no puppies!

-The house features a functional wood-burning fireplace. You will need to bring your own supply of firewood. We request that you only utilize the fireplace if you have prior experience and are familiar with how the flue operates. Please be cautious, as any smoke damage to the house will incur a fine.

No sweat on accidental & reported damage! Your rental includes an accidental reported damage waiver fee up to a maximum of $800. The cost to repair any accidental and reported damage to the rented property including any missing or broken items up to a maximum of $800 will be covered at no charge to you as long the damage is reported to your Host before you depart.
*Damage caused by smoke or pets is not covered by the accidental damage waiver.

- "We could not have been more happy with our stay. The house was clean, beautifully designed, had loads of amenities and was about a 15 minute drive to all the action in Great Barrington. The owners were very communicative and pleasant to work with. It was our first trip to the Berkshires but won’t be the last and we’ll definitely stay here again. 5 adults and 2 teens - plenty of space for all and 2 bathrooms/showers worked out fine." - "This was a very lovely home to stay in for our family, everything you need is in the house (basic things minus food of course) We would definitely book this house again when we visit the Berkshires again."

A wonderful Berkshire vacation home for the entire family to enjoy! This charming and spotless home is fully wheelchair/handicapped accessible, if needed for someone with mobility issues. It has 5 bedrooms, 3 full bathrooms and 2 half-baths. Included in all this, there is an attached one bedroom apartment, which can double as a home office.
The house has a large open, fully equipped kitchen with a dining table that accommodates 10. Family and friends can relax in the huge screened-in porch room, or in the large living room with Smart TV, including Netflix and Amazon Prime. An outdoor deck off the kitchen and covered front porch are also spaces for sitting and relaxing.
Master bedroom on the first floor has a king bed, and large private bath with grab bars by the toilet and in the roll-in shower. A separate bath tub is in this bathroom as well. There is also a second bedroom/office with private half bath on the first floor. Upstairs are 2 more bedrooms and a full bathroom, one with a queen bed, and one with a double bed.
The attached apartment(separate entrance) has a living room with couch, small kitchenette, separate bedroom with double bed, and full bathroom.
The home provides Fiber Connect high speed(500+Mbps upload and download) Internet and WiFi. There is a full size crib and children’s equipment(gate, high chair, toys, etc) if needed. The upstairs bedrooms(mini-splits) and the master bedroom(window A/C) have air conditioners for the few days where A/C is needed. These cool the entire first and second floor if needed for daytime use.
The house is perfectly located for lots of summer fun. The 5 acre property is directly across the road from championship caliber Arthur Ashe tennis courts, which can be reserved for use free of charge. They are part of the beautiful 100-acre French Park which also has well maintained tennis and pickleball courts, children's playground hiking trails and so much more. A short walk takes you to pristine Prospect Lake, where you can swim, canoe or kayak. A few steps in the other direction takes you to the “Olde Egremont Country Store”, well-stocked with everything from fishing worms to single malt scotch, and of course plenty of snacks. A leisurely walk to the top of Baldwin Hill provides views that will take your breath away. Great Barrington, proclaimed “America’s Best Small Town” by travel magazines, has many wonderful shops and restaurants, and is 4 miles away(5-7min). Tanglewood Music Center is a scenic 20min drive, Stockbridge(Norman Rockwell town) a few minutes less, and trendy Hudson, NY is 25min.
Music, theatre, food, outdoor activities and just plain relaxation! Good times with family and friends. Our home awaits you for all this and more!

- "My husband and I and 4 other adult family members stayed in this lovely Berkshires home for a week, and had a lovely, relaxing stay. The house is quite spacious, with lots of separate areas (including several porches) for people to hang out without feeling like you're on top of each other. The description made it sound like there was only one full bathroom (or perhaps I just misread it), but there are in fact two, as well as two other half baths (and I believe another bath in the basement apartment). The kitchen is enormous, and incredibly well-stocked: pots, pans, coffee maker, utensils - really almost anything you could want (including a pretty decent selection of spices, flours, etc.). The house itself is also very well stocked, with extra towels, sheets, etc. all readily available. William replied quickly to all of our questions, both before and during our stay, and gave us detailed instructions (including a binder with information about local attractions and advice to help up get the most out of our stay). The location is great - just about 10 minutes to Great Barrington, and about 25 to Lenox. We enjoyed our week immensely, and look forward to hopefully returning in future summers!"