Vacation rentals in West Stockbridge

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Top-rated vacation rentals in West 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

R2,945 ZAR 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

R2,369 ZAR 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

R1,884 ZAR 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

R2,121 ZAR 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

Welcome to "The Tiny" at The Hemptons in Upstate New York! The not-so-tiny house is 400sf with plenty of space to stretch out. Each of the two bedroom lofts have a comfy queen bed on a low profile frame. The kitchen is equipped for basic cooking (read: Not good for Thanksgiving, but perfectly suited for standard cooking endeavors). Although we'd encourage you to check out many the local eateries (see below)! The bathroom is full size and likely bigger than the one in your first NYC apartment.

Aug 6 – 13

R2,913 ZAR per night

Guest favorite

Cottage in Hillsdale

4.94 out of 5 average rating, 171 reviews

Cozy Cottage Catamount, Berkshires Walk to Brewery

This cute, cozy cottage is located in the center of Hillsdale, NY on the grounds of the Second Empire landmark Mount Washington House, located in the hamlet’s National Historic District. The cottage is perfectly located between Hudson, NY and Great Barrington, MA and you can walk to stores, parks, Roe Jan Brewing Company, Taconic Ridge, the Harlem Valley Rail Trail and more. Very close to Catamount Mountain Resort, Copake Lake and Bash Bish Falls. Public EV charger located in west lot.

Feb 15 – 22

R2,385 ZAR per night

Guest favorite

Home in West Stockbridge

4.87 out of 5 average rating, 102 reviews

Peaceful Stockbridge Cabin in the Woods

The Residence is a beautiful, secluded home in the Berkshire foothills. The 14-acre property includes hiking trails through the woods, a meadow, and a lovely babbling brook. Despite its secluded feel, the house just a short drive from many of the area's favorite attractions. The Residence provides a wonderful for base for enjoying all that the Berkshires have to offer, though guests may decide to spend much of their stay exploring the rustic beauty of the property itself.

Sep 23 – 30

R6,334 ZAR 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

R2,781 ZAR 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 18 – 25

R2,889 ZAR 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

R3,200 ZAR 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

R1,672 ZAR 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

R3,956 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for West Stockbridge vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near West Stockbridge's top sights

No. Six Depot Roastery & Cafe82 locals recommend

Chesterwood63 locals recommend

Shaker Mill Tavern4 locals recommend

Rouge Restaurant33 locals recommend

Public Market6 locals recommend

Turn Park Art Space10 locals recommend

Other great vacation rentals in West Stockbridge

Guest favorite

Cottage in Great Barrington

4.91 out of 5 average rating, 224 reviews

Cottage on Scenic Road

Dec 11 – 18

R2,584 ZAR per night

Guest favorite

Cottage in Great Barrington

4.98 out of 5 average rating, 126 reviews

Newly built cottage on working farm

Oct 23 – 30

R2,192 ZAR 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

R2,738 ZAR per night

Guest favorite

Cabin in Stockbridge

4.88 out of 5 average rating, 189 reviews

Hip Stockbridge Cabin - A stroll to the lake

Feb 17 – 24

R8,722 ZAR per night

Guest favorite

Home in Canaan

5.0 out of 5 average rating, 133 reviews

Country Cottage

Jan 26 – Feb 2

R2,928 ZAR per night

Guest favorite

Guest suite in Great Barrington

5.0 out of 5 average rating, 42 reviews

Sweet 1-bedroom with salt water pool

Jun 6 – 13

R2,473 ZAR per night

Guest favorite

Home in Lee

5.0 out of 5 average rating, 35 reviews

GreenHouse

Sep 3 – 10

R2,721 ZAR per night

Guest favorite

Home in West Stockbridge

4.94 out of 5 average rating, 18 reviews

Loft Style Cabin In West Stockbridge, Book Now!

Oct 30 – Nov 6

R4,940 ZAR per night

Show all

Quick stats about vacation rentals in West Stockbridge

Total rentals
60 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
50 properties are a good fit for families
Total number of reviews
1.9K reviews
Nightly prices starting at
R1,331 ZAR before taxes and fees

Frequently Asked Questions

Do house rentals in West Stockbridge have wifi?
Absolutely! We offer over 40 house rentals with wifi in West Stockbridge. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in West Stockbridge?
Experience the best of West Stockbridge with our house rentals, starting at about $70 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 West Stockbridge have free parking?
Absolutely! We offer over 40 house rentals with free parking in West Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in West Stockbridge have a kitchen?
Absolutely! We offer over 40 house rentals with a kitchen in West Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in West Stockbridge?
Four-legged friends are welcome in West Stockbridge. Choose from more than 20 vacation rentals for guests traveling with pets.
What are the most popular amenities for House Rentals in West Stockbridge?
Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with a kitchen, over 40 homes with wifi, over 40 homes with air conditioning, over 40 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in West Stockbridge have air conditioning?
Absolutely! We offer over 40 house rentals with air conditioning in West Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in West Stockbridge?
Yes! Work meets play with ease at over 30 vacation rentals in West Stockbridge featuring dedicated workspaces. Stay connected and productive in your home away from home.

Vacation rentals in West Stockbridge

Top-rated vacation rentals in West Stockbridge

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for West Stockbridge vacation rentals

Stay near West Stockbridge's top sights

Other great vacation rentals in West Stockbridge

Cottage in Great Barrington

Cottage in Great Barrington

Home in New Lebanon

Cabin in Stockbridge

Home in Canaan

Guest suite in Great Barrington

Home in Lee

Home in West Stockbridge

Quick stats about vacation rentals in West Stockbridge

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in West Stockbridge have wifi?

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

Do house rentals in West Stockbridge have free parking?

Do house rentals in West Stockbridge have a kitchen?

Are there pet-friendly vacation rentals in West Stockbridge?

What are the most popular amenities for House Rentals in West Stockbridge?

Do house rentals in West Stockbridge have air conditioning?

Are there vacation rentals with a dedicated workspace in West Stockbridge?

Destinations to explore