Vacation rentals in Stockbridge Bowl
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Top-rated vacation rentals in Stockbridge Bowl
Guests agree: these stays are highly rated for location, cleanliness, and more.
Home in Lee
4.89 out of 5 average rating, 234 reviewsCozy Berkshires Cottage
Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)
Sep 13 – 20
Apartment in Copake Falls
4.93 out of 5 average rating, 250 reviewsModern Copake Falls Getaway - 8 Mins to Catamount
Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!
Sep 13 – 20
Treehouse in Tyringham
5.0 out of 5 average rating, 222 reviewsGingerbread 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.
May 9 – 16
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Stockbridge Bowl vacation rentals
Other great vacation rentals in Stockbridge Bowl
Home in Lenox
4.86 out of 5 average rating, 328 reviewsBerkshire, MA Getaway! Mile to town
Jul 15 – 22
Tiny home in Chatham
4.99 out of 5 average rating, 178 reviewsTiny House on 70 Private Acres in Hudson Valley
Jun 8 – 15
Home in Canaan
5.0 out of 5 average rating, 132 reviewsCountry Cottage
Dec 27 – Jan 3
Home in Lee
4.9 out of 5 average rating, 202 reviews1817 Berkshire Farmhouse- Close to Everything.
Sep 4 – 11
Cottage in Great Barrington
4.93 out of 5 average rating, 234 reviewsArtist Cottage
Jul 20 – 27
Cottage in Stockbridge
5.0 out of 5 average rating, 21 reviewsQuiet 2 BR cottage in the heart of the Berkshires
Sep 21 – 28
Home in Stockbridge
5.0 out of 5 average rating, 32 reviewsRelaxing Berkshire Retreat with Lake Access
Apr 7 – 14
Home in Stockbridge
5.0 out of 5 average rating, 34 reviewsNew Construction in Stockbridge - Lake Community
May 16 – 23
Apartment in Canaan
5.0 out of 5 average rating, 81 reviewsMountain View Getaway
Nov 24 – Dec 1
Home in Lee
5.0 out of 5 average rating, 33 reviewsGreenHouse
Aug 30 – Sep 6
Home in Stockbridge
4.88 out of 5 average rating, 26 reviewsStockbridge Cape Near Tanglewood!
Dec 7 – 14
Home in West Stockbridge
5.0 out of 5 average rating, 52 reviewsHeart of the Berkshires - Bright, Cozy, Near Lake
Apr 19 – 26
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