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.

Guest favorite

Home in Lee

4.89 out of 5 average rating, 234 reviews

Cozy 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

R2,363 ZAR per night
Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 250 reviews

Modern 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

R2,030 ZAR per night
Guest favorite

Treehouse in Tyringham

5.0 out of 5 average rating, 222 reviews

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.

May 9 – 16

R5,110 ZAR per night

Popular amenities for Stockbridge Bowl vacation rentals

Other great vacation rentals in Stockbridge Bowl

Superhost

Home in Lenox

4.86 out of 5 average rating, 328 reviews

Berkshire, MA Getaway! Mile to town

Jul 15 – 22

R7,764 ZAR per night
Guest favorite

Tiny home in Chatham

4.99 out of 5 average rating, 178 reviews

Tiny House on 70 Private Acres in Hudson Valley

Jun 8 – 15

R2,906 ZAR per night
Guest favorite

Home in Canaan

5.0 out of 5 average rating, 132 reviews

Country Cottage

Dec 27 – Jan 3

R2,921 ZAR per night
Guest favorite

Home in Lee

4.9 out of 5 average rating, 202 reviews

1817 Berkshire Farmhouse- Close to Everything.

Sep 4 – 11

R4,839 ZAR per night
Guest favorite

Cottage in Great Barrington

4.93 out of 5 average rating, 234 reviews

Artist Cottage

Jul 20 – 27

R4,588 ZAR per night
Guest favorite

Cottage in Stockbridge

5.0 out of 5 average rating, 21 reviews

Quiet 2 BR cottage in the heart of the Berkshires

Sep 21 – 28

R5,551 ZAR per night
Guest favorite

Home in Stockbridge

5.0 out of 5 average rating, 32 reviews

Relaxing Berkshire Retreat with Lake Access

Apr 7 – 14

R9,808 ZAR per night
Guest favorite

Home in Stockbridge

5.0 out of 5 average rating, 34 reviews

New Construction in Stockbridge - Lake Community

May 16 – 23

R8,272 ZAR per night
Guest favorite

Apartment in Canaan

5.0 out of 5 average rating, 81 reviews

Mountain View Getaway

Nov 24 – Dec 1

R2,005 ZAR per night
Guest favorite

Home in Lee

5.0 out of 5 average rating, 33 reviews

GreenHouse

Aug 30 – Sep 6

R2,699 ZAR per night
Guest favorite

Home in Stockbridge

4.88 out of 5 average rating, 26 reviews

Stockbridge Cape Near Tanglewood!

Dec 7 – 14

R4,141 ZAR per night
Guest favorite

Home in West Stockbridge

5.0 out of 5 average rating, 52 reviews

Heart of the Berkshires - Bright, Cozy, Near Lake

Apr 19 – 26

R8,274 ZAR per night

Destinations to explore