Vacation rentals in Stockbridge

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Top-rated vacation rentals in Stockbridge

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Guest favorite

Home in Lee

4.9 out of 5 average rating, 202 reviews

1817 Berkshire Farmhouse- Close to Everything.

*Close to ski resorts & tubing! We are nestled at the foot of October Mountain State Forest, yet close to the centers of Lee, Lenox, & Pittsfield. Our charming house was built in 1817- original wood beams, wood floors, and quite a history. Whether you enjoy skiing, exploring local restaurants & downtowns, venturing outdoors or experiencing the local art scene, the Berkshires has something for everyone. Our little farmhouse serves as the perfect "home base" for all of your Berkshire adventures.

Apr 24 – May 1

€ 183 per night

Guest favorite

Home in Lee

4.89 out of 5 average rating, 235 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 26 – Oct 3

€ 146 per night

Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 255 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!

Oct 14 – 21

€ 116 per night

Guest favorite

Treehouse in Tyringham

5.0 out of 5 average rating, 225 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.

Jul 21 – 28

€ 329 per night

Superhost

Apartment in Lee

4.78 out of 5 average rating, 106 reviews

Cozy Berkshire Cottage Style Apartment

Stay in a cozy Berkshires apartment! All windows allow views to the peaceful surrounding state forest and yard. Watch humming birds, oriols, deer, squirrels, opossums, racoons, woodchucks, and many more... The house is set back from the road, easily accessible, yet private. The cottage is a duplex: the Airbnb apartment is on the left side of the cottage. • Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Stockbridge, Lenox, MA Turnpike • Ideal for lovers of nature & the Berkshires

Sep 9 – 16

€ 129 per night

Guest favorite

Guesthouse in Becket

4.93 out of 5 average rating, 257 reviews

Country Cabin

Lovely private country setting. Listen to owls and coyotes at night, birds during the day. When it rains you can enjoy the sound on the metal roof. I only accept advance reservations of 2 nights or more. (You may reserve a single night booking within 5 days of the request.) The space is for 2 adults but I allow for flexibility, so don't hesitate to ask. Seasonal/weekend rates may apply. I live on the property with my partner and the cabin would not otherwise be on the real estate market.

Jan 1 – 8

€ 131 per night

Guest favorite

Cabin in Stockbridge

4.88 out of 5 average rating, 189 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 cozy sleeping loft. A 8-10 minute walk or 2 minute drive to lake public beach (The lovely Stockbridge Bowl) Outdoor shower. BBQ grill, great outdoor space to play.

Feb 17 – 24

€ 512 per night

Guest favorite

Guesthouse in Lenox

4.95 out of 5 average rating, 275 reviews

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.

Sep 6 – 13

€ 158 per night

Guest favorite

Farm stay in Pittsfield

4.99 out of 5 average rating, 105 reviews

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 take a walk on our hiking trail.

Jul 19 – 26

€ 164 per night

Guest favorite

Guesthouse in Stockbridge

4.96 out of 5 average rating, 175 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 brand 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.

Jun 4 – 11

€ 188 per night

Superhost

Guest suite in Austerlitz

4.86 out of 5 average rating, 137 reviews

Rustic-Modern Studio - Near Hudson, Chatham, & GB

Get a small rustic-modern cabin feel in this cozy and self-sufficient space. 10 minutes from Chatham, 15-20 minutes from Great Barrington, Lee, Lenox, Kripalu Center for Yoga & Health, Catamount Ski Resort, TangleWood Institute and seconds away from a beautiful hike up Harvey Mountain in Austerlitz, NY. The wood-stove will keep you warm in the winter months and the large field and creek in the backyard will relax you in the summer.

Nov 26 – Dec 3

€ 84 per night

Guest favorite

Cottage in West Stockbridge

4.98 out of 5 average rating, 106 reviews

Historic 1810 Farmhouse - Fully Renovated

Charm and history meet modern convenience in this stunning renovated farmhouse. Built in 1810, this beautiful home was once the residence of Mr. Prince, who presided over the Tobey Quarry Farm. Just steps into town, the cottage is the ideal retreat for a low-key, cozy getaway. Or as a launch pad to the area's many outdoor/cultural offerings. We warmly welcome you!

Jun 3 – 10

€ 233 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Stockbridge vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Stockbridge's top sights

Norman Rockwell Museum344 locals recommend

The Red Lion Inn117 locals recommend

Naumkeag109 locals recommend

Berkshire Botanical Garden118 locals recommend

Kripalu Center For Yoga & Health122 locals recommend

Michaels of Stockbridge7 locals recommend

Other great vacation rentals in Stockbridge

Guest favorite

Cottage in Great Barrington

4.98 out of 5 average rating, 125 reviews

Newly built cottage on working farm

Oct 23 – 30

€ 124 per night

Guest favorite

Tiny home in Chatham

4.99 out of 5 average rating, 180 reviews

Tiny House on 70 Private Acres in Hudson Valley

Aug 6 – 13

€ 156 per night

Guest favorite

Apartment in Lenox

4.88 out of 5 average rating, 169 reviews

Station House 1E Private Room & Bath

Jun 17 – 24

€ 82 per night

Guest favorite

Home in Stockbridge

4.95 out of 5 average rating, 103 reviews

Sun-filled, Charming Stockbridge Classic- In Town!

Mar 19 – 26

€ 322 per night

Guest favorite

Home in New Lebanon

4.99 out of 5 average rating, 348 reviews

The old sawmill from 1771

Mar 5 – 12

€ 146 per night

Guest favorite

Home in Canaan

5.0 out of 5 average rating, 133 reviews

Country Cottage

Jan 26 – Feb 2

€ 146 per night

Guest favorite

Guest suite in South Lee

4.92 out of 5 average rating, 190 reviews

Sunny Riverside Apartment

May 8 – 15

€ 185 per night

Guest favorite

Home in Lee

5.0 out of 5 average rating, 35 reviews

GreenHouse

Sep 3 – 10

€ 167 per night

Show all

Quick stats about vacation rentals in Stockbridge

Total rentals
130 properties
Rentals with a pool
30 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
3.6K reviews
Nightly prices starting at
€ 94 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 house rentals in Stockbridge?
Experience the best of Stockbridge with our house rentals, starting at about $100 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 30 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 gym?
Absolutely! We offer over 10 house rentals with a gym in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Stockbridge have a bbq area?
Absolutely! We offer over 10 cabin rentals with a bbq area in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Boutique Hotel Rentals in Stockbridge?
Enhance your stay in our Boutique Hotel Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Stockbridge

Top-rated vacation rentals in Stockbridge

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Stockbridge vacation rentals

Stay near Stockbridge's top sights

Other great vacation rentals in Stockbridge

Cottage in Great Barrington

Tiny home in Chatham

Apartment in Lenox

Home in Stockbridge

Home in New Lebanon

Home in Canaan

Guest suite in South Lee

Home in Lee

Quick stats about vacation rentals in Stockbridge

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Stockbridge have air conditioning?

Are there pet-friendly vacation rentals in Stockbridge?

Are there family-friendly vacation rentals in Stockbridge?

How much does it cost to stay in house rentals in Stockbridge?

Do house rentals in Stockbridge have wifi?

Are there vacation rentals with a dedicated workspace in Stockbridge?

Are there Stockbridge vacation rentals on Airbnb with pools?

Do house rentals in Stockbridge have a gym?

Do cabin rentals in Stockbridge have a bbq area?

What are the most popular amenities for Boutique Hotel Rentals in Stockbridge?

Destinations to explore