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 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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, (1,128 reviews)
"Clean & comfortable stay"
United States
Robert
$113 nightly
The price is $126
Oct 1 - Oct 2
Total with taxes and fees
Berkshire Mountain Lodge
Interior

2. 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.
$286 nightly
The price is $319
Sep 9 - Sep 10
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
Interior

3. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
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 8 - Sep 9
Total with taxes and fees
Riverside Retreat in the Berkshires
Private kitchen

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.4 out of 10, Exceptional, (3 reviews)
"Great location, great property, great host"
United States
Shelly B.
$148 nightly
The price is $165
Sep 13 - Sep 14
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
Private kitchen

5. 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)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
$204 nightly
The price is $207
Sep 10 - Sep 11
Total with taxes and fees
NEW RENO - Chalet-style farm loft near Tanglewood
Lobby

6. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,610 reviews)
"All the amenities offered are an excellent plus. Good rates for rooms. Good place to stay at, lots to do even around the area"
United States
Alex
$122 nightly
The price is $136
Sep 7 - Sep 8
Total with taxes and fees
Vacation Village in the Berkshires
Living area

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.
$221 nightly
The price is $224
Sep 9 - Sep 10
Total with taxes and fees
1800s Carriage house in Berkshires / Hudson Valley
Living area

8. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Lenox
$285 nightly
The price is $318
Sep 8 - Sep 9
Total with taxes and fees
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Exterior

9. 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.
$489 nightly
The price is $496
Sep 9 - Sep 10
Total with taxes and fees
1789 Shaker Farmhouse in Berkshires/Hudson Valley
Exterior

10. 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, (40 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
$766 nightly
The price is $856
Sep 28 - Sep 29
Total with taxes and fees
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Private kitchen

11. 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.
$276 nightly
The price is $308
Sep 8 - Sep 9
Total with taxes and fees
Home in Great Barrington
Beach

12. 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.
$283 nightly
The price is $316
Sep 14 - Sep 15
Total with taxes and fees
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Property grounds

13. 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, (13 reviews)
"This property is really nice. House is beautiful and the man cave is a nice addition. Wish we were there long enough to use it."
United States
Jen R.
$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.
Private kitchen

14. 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)
"Excellent area for hiking the Berkshires! House is clean, comfortable, and perfect for cooking a quick dinner after showering off the mud and pine needles. Dog friendly. Right off the main street of a very nice neighborhood."
United States
Elizabeth G.
$290 nightly
The price is $323
Sep 10 - Sep 11
Total with taxes and fees
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Terrace/patio

15. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (79 reviews)
"Excellent host!"
United States
Kenny
$339 nightly
The price is $380
Sep 7 - Sep 8
Total with taxes and fees
Ideal location for summer and winter activities with plenty of outdoor space.
Room

16. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
$496 nightly
The price is $554
Sep 14 - Sep 15
Total with taxes and fees
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Gift shop

17. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly."
United States
Ann
$209 nightly
The price is $233
Sep 9 - Sep 10
Total with taxes and fees
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Living area

18. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
$546 nightly
The price is $577
Sep 21 - Sep 22
Total with taxes and fees
Treetop Hideaway in Tyringham
Terrace/patio

19. BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
$292 nightly
The price is $329
Sep 8 - Sep 9
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
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 Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"Excellent staff and excellent Indian restaurant!!! Hotel a little dated, but beds were comfortable and staff was great!"
Susan 1-night trip
Posted 4 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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 $126 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 Charles H. Baldwin & Sons, 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 Charles H. Baldwin & Sons and Ebenezer II Gifts and Antiques, whereas Stockbridge Bowl is a spot to enjoy the outdoors. Hoffman's Pottery and Berkshire Botanical Garden are a couple of places you'll find in the larger area.

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.