Holiday rentals in Stockbridge Bowl

4.94 out of 5 average rating, 418 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

4.97 out of 5 average rating, 365 reviews

Tiny home in Tyringham

Enchanted Tiny Tower nestled in the Berkshires

Whimsical and romantic tower on the Santarella Estate in Tyringham, MA in the heart of the Berkshires. Live out your fairytale in this two-story unique, tiny home. First floor offers 3 rooms in one with kitchenette, sitting area, and dining room looking out on to the babbling brook. Upper bedchamber with canopied bed provides amazing views of sky and trees through massive, mill windows. Perfect destination for a relaxing getaway or special stay while exploring all the Berkshires has to offer.

4.94 out of 5 average rating, 34 reviews

Cottage in Stockbridge

Quiet 2 BR cottage in the heart of the Berkshires

Welcome to our rustic and relaxing cottage in the woods, in the private community of Mahkeenac Heights, a 5-minute walk from the Stockbridge Bowl town beach, 2 miles from Tanglewood, 3 miles from Stockbridge and Lenox and close to all of the attractions of Berkshire County –music, dance, theatre, hiking, cycling, kayaking, swimming, fishing, great dining, wine bars, shopping, farmers’ markets, gardens, museums, galleries, stately homes, small town libraries, and coffee shops. The list goes on.

4.98 out of 5 average rating, 43 reviews

Lakeshore cabin with beach and dock

A classic Berkshire cabin nestled under maple trees, on the shore of the Stockbridge Bowl cove. Serene, peaceful and private, yet close to all area attractions. Newly renovated. Large light-filled living room with cathedral ceiling and skylights. Main bedroom on ground floor with bathroom. Enclosed porch and large deck with gas grill. Swimming and kayaking off the dock. Large lawn with lots of trees. Forest trail and waterfall next door. Plenty of parking. 5 minutes to Tanglewood and Kripalu.

Superhost

4.88 out of 5 average rating, 218 reviews

Hip Stockbridge Cabin - A stroll to the lake

Hello hip, glamping cabin! The decor is chic & bohemian cool! Enjoy the large yard & sunny deck. Fieldstone fireplace w/ vaulted ceilings & skylights. Cottage has beautiful pine throughout w/ fabulous interior design picks. Enjoy the sweet reading nook, master bedroom w/ skylights or put on a favorite record. Kids will love the sleeping loft. A 9 minute walk or 2 minute drive to lake public beach (The lovely Stockbridge Bowl) . BBQ grill, outdoor fire pit . Gates of Tanglewood minutes aaway!

4.97 out of 5 average rating, 215 reviews

Home in Lee

Berkshire 4 season home

The house is located in the heart of the Berkshires. It's less than 10 miles from Tanglewood, Kripalu, Jacob's pillow Dance, Monument Mountain, Beartown state forest, Norman Rockwell Museum, Shakespeare & Co., Ski Butternut, Lee Prime outlets. Located 1.5 miles from the turnpike exit for easy travel, 3 miles from Laurel lake, walking distance to a public golf course and downtown Lee where you will find great restaurants. There is Cable internet that is fast and reliable if you have to work.

4.96 out of 5 average rating, 106 reviews

Flat in Stockbridge

Historic,Famous,Iconic, Unforgettable Berks Escape

PICTURE IT...You can put yourself in the "famed" Norman Rockwell Main Street at Christmas Painting! That's Right,Cozy, Intimate,Magical and all to yourself.Fully equipped with all the comforts of home. Small Town Charm,Big time Historic setting in the heart of Downtown Stockbridge! Spend your afternoon sipping Tea or Wine looking out the iconic picture window Norman Rockwell installed himself. The one where the Christmas Tree Glows in a room that was Norman Rockwell's Studio from 1953-1957

4.96 out of 5 average rating, 27 reviews

Stockbridge Snug- cabin luxury just steps to lake!

The Snug (an energy efficient home) was designed, renovated, and completed in June 2022. It serves as a cozy haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, attend a Tanglewood concert, take in a play, or just hot tub amongst the trees- we hope you enjoy your stay and will visit us again.

4.99 out of 5 average rating, 222 reviews

Farm stay in Pittsfield

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

4.93 out of 5 average rating, 376 reviews

Guest house 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.

Guest house 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.

Guest house in Stockbridge

4.91 out of 5 average rating, 128 reviews

Modern barn in the heart of the Berkshires

Modern, renovated, historic dairy barn in the heart of the Berkshires. Located on 3.5 acres with beautiful views and close to everything. 1.5 miles to Main St Stockbridge/Red Lion Inn, 5 minutes to Tanglewood, 5 minutes to the Stockbridge Bowl and beautiful hiking trails, under 10 minutes to Lenox . This is the perfect base for exploring the Berkshires or a great getaway for relaxing and enjoying nature.

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Other great holiday rentals in Stockbridge Bowl

Guest house in Stockbridge

4.72 out of 5 average rating, 92 reviews

Guest House in Stockbridge 3 miles to Tanglewood

LaraRating, 5 stars10 months ago

This was our first trip to the Berkshires and it couldn’t have been more perfect. Tracey and Sean really host a home away from home that’s probably as close to feeling like a local as you’re going to get in this magical region. We’ll be back!

Cottage in West Stockbridge

4.97 out of 5 average rating, 34 reviews

Tanglewood Cottage in the heart of the Berkshires

LuRating, 5 stars10 months ago

This was our second stay here, and we will hope to be back again next year. Less than three miles from Tanglewood, plus nearby hiking trails & historic sites, the location gave us plenty to do. The home is sparkling clean, has lots of towels, pillows, etc. Screened porch, deck, heat & AC if needed. Barred owls call during the night. Hosts live next door beyond the trees. Excellent communication if needed.

5 out of 5 average rating, 67 reviews

Home in Canaan

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

LisaRating, 5 stars1 week ago

The house was perfect! Beautiful property, lovely house, responsive hosts.

Cabin in West Stockbridge

5 out of 5 average rating, 7 reviews

Serene rustic mountain cabin in the Berkshires!

KellyRating, 5 stars1 month ago

Would love to come Back!

5 out of 5 average rating, 39 reviews

Cabin in Saugerties

Luxury A-Frame Cabin w/ Hot Tub

AmandaRating, 5 starstoday

We had a serene and luxurious stay at Fil and Ellie’s. The inside of the home is comfortable and they seem to have thought of every detail. We so enjoyed the peace and quiet, the views of the beautiful trees, and our soaks in the tub. This felt like a private oasis- a true slice of heaven.

4.71 out of 5 average rating, 34 reviews

Cozy Stockbridge Cabin - Walk to Beach & Lake!

Teresa PrinsterRating, 5 stars20 months ago

Peaceful quiet private New England home with thoughtful updates. The Fall chill went quickly on arrival and the rest of. the was cozy warm. Great wifi.