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Vacation rentals in West Stockbridge

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Top-rated vacation rentals in West Stockbridge

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Home in Lee

4.9 out of 5 average rating, 253 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)

Home in Stockbridge

4.95 out of 5 average rating, 110 reviews

Bright Stockbridge country home, near everything!

Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

Cottage in Great Barrington

4.93 out of 5 average rating, 266 reviews

Artist Cottage

Enchanting, private, romantic, retro style, artsy, cottage & lodge building with fireplaces and outdoor hot tub and shower area in a quaint, quiet, neighborhood nested at the base of Flag Rock and near nature trails and downtown Great Barrington. Perfect for a romantic get-away. Open retro style kitchen with wood stove and TV is stocked with utensils and pans for cooking with gas oven and retro appliances. Upstairs bedroom with ensuite large bathroom with soaking tub and message chair.

Rental unit in Canaan

4.99 out of 5 average rating, 147 reviews

Mountain View Getaway

Come relax & enjoy panoramic mountain and pond views. Marvel at the dramatic lighting effects on Mercer Mt from sunrise-sunset from your private deck or bright living room. Fully equipped kitchen, grill on the deck, short scenic drive to a wide variety of restaurants & endless cultural venues in the surrounding quaint villages of Berkshire County Mass and Columbia County NY. Near hiking trails, skiing, apple picking & farm stores. Queechy Lake swimming, NYS boat launch for car top boats.

Cabin in Stockbridge

4.87 out of 5 average rating, 206 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.

Cottage in Hillsdale

4.95 out of 5 average rating, 192 reviews

Cozy Cottage Berkshires & Hudson Hike Bike Zipline

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.

Farm stay in Pittsfield

4.99 out of 5 average rating, 170 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 just relax out on the balcony and take in the views.

Guesthouse in Lenox

4.94 out of 5 average rating, 341 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.

Guesthouse in Stockbridge

4.95 out of 5 average rating, 213 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 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.

Tiny home in Chatham

4.99 out of 5 average rating, 217 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). Regretfully, we are unable to accommodate service animals due to the health risk it poses it the owners.

Cabin in Chatham

4.97 out of 5 average rating, 118 reviews

The Upstate Cabin: A secluded getaway in the woods

Cozy cabin tucked away in the woods, 2.5 hours north of NYC and 2.5 hours west of Boston - where the Catskills meet the Berkshires. There's hiking in the summer, skiing in the winter, and total peace & quiet year-round. This entire cabin has been hand-lovingly restored and we can't wait to share the space with you. Follow us on Insta at @theupstatecabin to follow our upstate adventures and cabin transformation.

Cottage in West Stockbridge

4.97 out of 5 average rating, 126 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!

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Popular amenities for West Stockbridge vacation rentals

Free parking on premises

Air conditioning

Stay near West Stockbridge's top sights

Norman Rockwell Museum343 locals recommend

Berkshire Botanical Garden118 locals recommend

No. Six Depot Roastery & Cafe82 locals recommend

Berkshire Mountain Bakery Inc64 locals recommend

Chesterwood63 locals recommend

Olivia's Overlook51 locals recommend

Other great vacation rentals in West Stockbridge

Home in Stockbridge

4.98 out of 5 average rating, 42 reviews

Secluded Family Home in Serene Stockbridge Woods

Home in West Stockbridge

4.91 out of 5 average rating, 11 reviews

Family friendly house in woods

Home in Great Barrington

5 out of 5 average rating, 46 reviews

The Yellow Victorian With Chefs Kitchen

Rental unit in Stockbridge

5 out of 5 average rating, 35 reviews

Stockbridge private apartment

Home in Great Barrington

4.99 out of 5 average rating, 96 reviews

Granite Ledge, Modern home in a unique setting

Home in East Chatham

5 out of 5 average rating, 7 reviews

Stylish Rural Sanctuary

Home in Canaan

4.98 out of 5 average rating, 59 reviews

Crossings Cottage

Home in Great Barrington

4.9 out of 5 average rating, 91 reviews

Quiet home on the hill.

Quick stats about vacation rentals in West Stockbridge

Total rentals
60 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace

Frequently Asked Questions

Do house rentals in West Stockbridge have wifi?
Absolutely! We offer over 50 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 free parking, over 40 homes with air conditioning, over 40 homes with a kitchen, over 50 homes with wifi, 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.

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