A mountainous landscape with a lake and dense forests.

West Stockbridge Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for West Stockbridge vacation rentals

Lobby

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,086 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
$125 nightly
The price is $139
Aug 31 - Sep 1
Total with taxes and fees
Berkshire Mountain Lodge
Coffee/tea maker, fridge, microwave, oven

2. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
$200 nightly
The price is $202
Aug 23 - Aug 24
Total with taxes and fees
NEW RENO - Chalet-style farm loft near Tanglewood
Interior

3. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
$285 nightly
The price is $318
Sep 1 - Sep 2
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
Interior

4. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
$270 nightly
The price is $302
Sep 2 - Sep 3
Total with taxes and fees
Cozy Riverside Berkshires Retreat
Smart TV

5. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (4 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
$338 nightly
The price is $377
Sep 14 - Sep 15
Total with taxes and fees
stylish Berkshires Retreat
Coffee/tea maker, fridge, microwave, oven

6. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.0 out of 10, Wonderful, (2 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
$139 nightly
The price is $155
Aug 31 - Sep 1
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
TV, DVD player, books, video library

7. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
$236 nightly
The price is $240
Sep 14 - Sep 15
Total with taxes and fees
1800s Carriage house in Berkshires / Hudson Valley
Outdoor dining

8. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
$603 nightly
The price is $635
Aug 30 - Aug 31
Total with taxes and fees
Stockbridge In-town Escape
Beach nearby, sun loungers, beach towels

9. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
$295 nightly
The price is $329
Sep 13 - Sep 14
Total with taxes and fees
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Exterior

10. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
$537 nightly
The price is $545
Sep 9 - Sep 10
Total with taxes and fees
1789 Shaker Farmhouse in Berkshires/Hudson Valley
4 bedrooms, travel crib, WiFi, bed sheets

11. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
$782 nightly
The price is $873
Sep 2 - Sep 3
Total with taxes and fees
Stylish Mid-century Modern Berkshires Cape
Lobby

12. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,556 reviews)
"Place was clean and well equipped, pool and amenities were great too !"
United States
Nyra
$106 nightly
The price is $118
Sep 2 - Sep 3
Total with taxes and fees
Vacation Village in the Berkshires
Coffee/tea maker, fridge, microwave, oven

13. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (31 reviews)
"This was a wonderful place to stay. We especially loved the easy access to the toys so the kids could start playing while we unloaded the car. It was perfect and just what we needed."
United States
Megan A.
$293 nightly
The price is $327
Aug 31 - Sep 1
Total with taxes and fees
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Coffee/tea maker, fridge, microwave, oven

14. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
$366 nightly
The price is $409
Aug 24 - Aug 25
Total with taxes and fees
Home in Great Barrington
Property grounds

15. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (11 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
$307 nightly
The price is $344
Sep 20 - Sep 21
Total with taxes and fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Exterior

16. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (168 reviews)
"Clean, quiet and relaxing stay."
United States
Andrea
$139 nightly
The price is $155
Aug 24 - Aug 25
Total with taxes and fees
Micosta Leisure Inn
Exterior

17. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (39 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveler
$846 nightly
The price is $945
Sep 20 - Sep 21
Total with taxes and fees
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Desk, iron/ironing board, WiFi, bed sheets

18. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.6 out of 10, Excellent, (7 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
$181 nightly
The price is $203
Aug 23 - Aug 24
Total with taxes and fees
The Brooks Motel: Exceptional Suite
TV, DVD player, books

19. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Hancock
9.0 out of 10, Wonderful, (17 reviews)
"Great stay! Perfect location by the pool and nicely renovated as advertised!"
United States
Matthew B.
$220 nightly
The price is $246
Aug 25 - Aug 26
Total with taxes and fees
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Pool

20. Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (4 reviews)
"Quiet location"
United States
Alicia S.
$220 nightly
The price is $246
Aug 25 - Aug 26
Total with taxes and fees
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top West Stockbridge Hotel Reviews

The Yankee Inn

The Yankee Inn

8/10 Good
"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."
Luann 1-night trip
Posted less than an hour ago
The Yankee Inn

Find out more about West Stockbridge

Everything you need to know about West Stockbridge vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the West Stockbridge vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect West Stockbridge vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

West Stockbridge vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in West Stockbridge. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit West Stockbridge in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $118 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on West Stockbridge rentals

At Expedia, we put the best West Stockbridge vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top West Stockbridge rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream West Stockbridge vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around West Stockbridge. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in West Stockbridge?

Yes, we have vacation rentals in West Stockbridge close to Hotchkiss Mobile Studio, or you can select a more secluded option if you want a relaxing stay. Visitors to West Stockbridge speak positively about the gardens and restaurants in this destination. Make sure you have time to check out the forests and lake views during your trip.

What are some of the best vacation home rentals that West Stockbridge has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This highly rated vacation home rental in West Stockbridge is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in West Stockbridge?

With 21 Expedia vacation rentals, you're sure to find just the right place for your West Stockbridge stay.

What can I see and do in West Stockbridge?

Family-friendly attractions include Hotchkiss Mobile Studio and Charles H. Baldwin & Sons, whereas Stockbridge Bowl is a spot to enjoy the outdoors. While here, Ebenezer II Gifts and Antiques and Hoffman's Pottery are other places worth a visit.

What are vacation rentals like in West Stockbridge?

Vacation rentals are privately owned accommodations you can stay in for several days or more in West Stockbridge. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from shared hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for family trips.