Holiday houses in Tyringham

4.94 out of 5 average rating, 416 reviews

Chalet in Otis

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

4.99 out of 5 average rating, 296 reviews

Treehouse in Tyringham

Gingerbread House Tower in the Berkshire Hills

Escape to this newly renovated, off-beat retreat for a magical stay. Part of Tyringham’s Gingerbread House located on the Santarella Estate in the Berkshires, Western Mass. This one-of-a-kind loft with tower bedchamber offers guests a fairytale experience. The open concept living space filled with plants brings the outdoors inside and offers ample room to relax. If looking for activity, guests can spend the day on the grounds, walking nearby trails, or exploring the many nearby Berkshire towns.

4.98 out of 5 average rating, 213 reviews

Cabin in Cummington

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

4.9 out of 5 average rating, 107 reviews

Cottage in Becket

Stylish Shales Brook Cottage-Cozy up to happiness

Bright & inviting! Welcome to our charming cottage, a stylish 2-bedroom, 2-bath retreat by Shales Brook. Relax on cool evenings beside the vintage Malm wood-burning stove. Enjoy modern comforts with central air, a screened-in porch, and a deck overlooking the tranquil waters of Shales Brook. The soothing sounds of the brook enhance your stay.. Located near fabulous Berkshire attractions, fantastic hikes, 15 minutes to the town of Lee, minutes to Jacob‘s pillow and 20 minutes to Tanglewood,!

Apartment in Great Barrington

4.88 out of 5 average rating, 104 reviews

Kitchenette|King Bed|Couch

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. *1.5 miles to Downtown *1.3 miles to Mahaiwe Performing Arts Center *44 miles to Albany International Airport *4.5 miles to Great Barrington Airport *9.9 miles to Tanglewood KEY FEATURES *MCM Design *Plush King Sized Bed high end bed Linens *High Speed Internet *58"Tv with Hulu Live

Guesthouse in Great Barrington

4.96 out of 5 average rating, 124 reviews

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

4.82 out of 5 average rating, 111 reviews

Home in Tyringham

Treetop Hideaway in Tyringham

For your upcoming stay, look no further than this airy, secluded log cabin overlooking the beautiful Tyringham Valley. On the first floor, you will find a great room with vaulted ceilings and a fireplace, as well as a master suite, second bedroom, half bath and recently renovated kitchen. The second floor includes two more bedrooms and a bathroom. The exterior offers a screen porch with hot tub, wraparound deck and 35+ acres of woods bordering conservation land in Monterey.

4.95 out of 5 average rating, 281 reviews

Cabin in Monterey

Amazing Berkshire Mountains Cabin

Our incredible 4 bedroom home is situated on 2 beautiful secluded acres in picture perfect Monterey - the ultimate Berkshire County getaway, with modern kitchen, screened porch, 2 fireplaces a fabulous outdoor hot tub and a beautiful brook on the property. Enjoy hiking the Appalachian Trail in nearby Beartown State Forest or kayaking and swimming in the incomparable Lake Garfield. We are a quick ride to Ski Butternut, Catamount, Tanglewood, Lenox and Great Barrington.

4.95 out of 5 average rating, 274 reviews

Cottage in Becket

Berkshires Cottage by Lake. Year Round Adventures.

THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX(will consider pets.)(90 second walk through wooded path to lake)

4.93 out of 5 average rating, 375 reviews

Guesthouse in Lenox

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

4.97 out of 5 average rating, 261 reviews

Home in Great Barrington

Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

Guesthouse in Stockbridge

4.95 out of 5 average rating, 234 reviews

Modern studio with views of the treetops

Our Stockbridge studio is located at the heart of the Berkshires, just north of the center of town. It is a new, modern, second floor studio suitable for up to four adults with views of the surrounding woods, a large kitchenette and comfortable, spacious living space for relaxing in your home away from home. There is a full bath and a private entrance. It is perfect for a weekend getaway or a seasonal stay, whatever your heart desires.

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4.96 out of 5 average rating, 24 reviews

Cabin in Stockbridge

Stockbridge Snug- cabin luxury just steps to lake!

MichaelRating, 5 stars1 week ago

The Snug was exactly what we were looking for! A beautiful house on an amazing piece of property in a fantastic location for exploring the Berkshires. The entire environment was so peaceful and serene. On the inside the house was clean, comfortable, inviting and had everything we needed. The floor to ceiling windows looking out into the wooded back yard were one of our favorite features of the house. On our last day of our stay we were lucky enough to see a family of deer make their way through the back yard. The wood fired hot tub was magical and well worth the wait to heat up. The hosts were informative, responsive, helpful and very nice. They genuinely cared about our stay. Thank you McCaela and Joe for sharing your lovely house with us, we can't wait to come back!

4.76 out of 5 average rating, 92 reviews

Home in Great Barrington

Cozy Berkshire Getaway

TashaRating, 5 stars1 month ago

We were happy with this AirBNB and would stay here again. It was nice and quiet but a very short drive into Great Barrington. Close to lots of hiking. Updates have been made since some of the previous reviews. There are two couches in the living room and some of the stock items in the kitchen for convenience.

4.78 out of 5 average rating, 124 reviews

Villa in South Lee

Villa with Access to Amazing Amenities!

PamelaRating, 5 stars8 months ago

The place was great and wish i had more time there. We were just looking for a quick overnight with two bedrooms, which this was, but it seemed like a lovely place for a vacation.

4.89 out of 5 average rating, 9 reviews

Cottage in Otis

Cozy Cottage in the Berkshires

KurtRating, 5 stars9 months ago

The small home is located at the end of a 0.25 mile dirt road. There are only four homes on the road, though one is on the opposite side at the end of the road. If you are staying here you should be comfortable in an isolated location. There are no window treatments on the two sliding doors opening to the deck in the back of the home, though there is also nothing but woods in the back of the home. All that being said, the place was exceptionally clean for any Airbnb rental, much less one tucked back in the woods. While the small kitchen was missing a few expected items like steak knives, tea bags, and measuring cups, it should prove to be functional for most guests. There is a large TV in the large living room and the internet was fine for streaming without any issues. The bed was comfortable and a large dresser is available for storing clothes. Be aware that the only available heat is from a gas fireplace, two portable space heaters, and another space heater in the bathroom.

4.96 out of 5 average rating, 96 reviews

Apartment in Otis

Enjoy every season the Berkshires have to offer.

MarieRating, 5 stars5 days ago

We had a lovely relaxing time. The place was in a quiet, beautiful spot. Denise’s instructions were helpful and she was very welcoming. The place was spotless and the bed was extremely comfortable. We’d happily stay there again.

4.97 out of 5 average rating, 39 reviews

Cabin in Becket

Entire Private Log Cabin in the Berkshires

AlyssaRating, 5 stars8 months ago

We had such a great time staying at Bob’s cabin! The location and view are seriously stunning, especially since we got to catch the fall foliage at its peak. I spent hours just hanging out on the screened-in porch, taking it all in. We always travel with our dogs, so it was awesome to find a place that’s dog-friendly. The cabin was super clean, cozy, and had a nice stash of board games—we ended up playing Scrabble every night! The drive up was beautiful, but make sure to follow Bob’s directions because Google Maps told us to make a wrong left in the neighborhood, which was a bit tricky since we arrived after dark. Bob was super responsive and gave us some great local tips. All in all, we loved it and will definitely be booking again!

5 out of 5 average rating, 53 reviews

Farm stay in Chatham

Charming Cabin Studio Amid the Hudson Valley

MarineRating, 5 stars2 weeks ago

We had a wonderful stay! The location is incredible— peaceful, beautiful, and perfect for a weekend escape. The studio itself was spotless, well-equipped, very comfortable, and felt perfectly private. The entire farm setting was a real gem. Thank you for a lovely experience!