Vacation rentals in Stockbridge
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Top-rated vacation rentals in Stockbridge
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 vacation rentals
Other great vacation rentals in Stockbridge
Cottage in West Stockbridge
4.98 out of 5 average rating, 106 reviewsHistoric 1810 Farmhouse - Fully Renovated
Jun 3 – 10
Home in Dalton
4.91 out of 5 average rating, 112 reviewsThe Yellow House
Feb 12 – 19
Loft in Great Barrington
4.99 out of 5 average rating, 296 reviewsThe Old Red Barn
Apr 29 – May 6
Guest suite in Valatie
4.98 out of 5 average rating, 229 reviewsGuest Suite in Old Chatham Hunt Country
Apr 20 – 27
Guest suite in South Lee
4.92 out of 5 average rating, 189 reviewsSunny Riverside Apartment
May 28 – Jun 4
Apartment in Lenox
4.88 out of 5 average rating, 168 reviewsStation House 1E Private Room & Bath
May 4 – 11
Home in Stockbridge
4.95 out of 5 average rating, 103 reviewsSun-filled, Charming Stockbridge Classic- In Town!
Jan 27 – Feb 3
Guesthouse in Becket
4.93 out of 5 average rating, 257 reviewsCountry Cabin
May 6 – 13
Apartment in Canaan
5.0 out of 5 average rating, 81 reviewsMountain View Getaway
Nov 24 – Dec 1
Apartment in Stockbridge
4.96 out of 5 average rating, 85 reviewsHistoric,Famous,Iconic, Unforgettable Berks Escape
Apr 6 – 13
Home in Lee
5.0 out of 5 average rating, 33 reviewsGreenHouse
Aug 30 – Sep 6
Home in Stockbridge
4.94 out of 5 average rating, 87 reviewsBright Stockbridge country home, near everything!
Dec 6 – 13
Quick stats about vacation rentals in Stockbridge
Total rentals | 140 properties |
---|---|
Rentals with a pool | 40 properties have a pool |
Pet-friendly rentals | 30 properties allow pets |
Family-friendly rentals | 80 properties are a good fit for families |
Total number of reviews | 3.5K reviews |
Nightly prices starting at | G$20,939 GYD before taxes and fees |
Frequently Asked Questions
Do house rentals in Stockbridge have air conditioning?
Absolutely! We offer over 60 house rentals with air conditioning in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Stockbridge?
Four-legged friends are welcome in Stockbridge. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there family-friendly vacation rentals in Stockbridge?
Stockbridge has more than 80 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in boutique hotel rentals in Stockbridge?
Experience the best of Stockbridge with our boutique hotel rentals, starting at about $990 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Stockbridge have wifi?
Absolutely! We offer over 60 house rentals with wifi in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Stockbridge?
Yes! Work meets play with ease at over 60 vacation rentals in Stockbridge featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Stockbridge vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Stockbridge, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Stockbridge have a bbq area?
Absolutely! We offer over 40 house rentals with a bbq area in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
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