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Compare 94 Apartments in West Stockbridge with updated reviews, rates, and availability.

Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Living area

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.6 out of 10, Exceptional, (8)
"Super cute, cozy and excellent location. Loved our stay. Will be back!"
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!
Living area

Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Was a great spot to enjoy Jiminy Peak!"
Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (60)
"Beautiful property with flower farm, pick your own berries and vegetable farm stand. Rustic log cabin feel with all amenities needed with kitchen."
The price is AED 533
AED 797 total
includes taxes & fees
23 Dec - 24 Dec
Cozy Rustic Apt in 18th c Berkshire Farmhouse
The Penthouse, Downtown Lenox by Evergreen Home
Gorgeous open concept living room

The Penthouse, Downtown Lenox by Evergreen Home

10.0 out of 10, Exceptional, (6)
"Amazing space and location!"
The Penthouse, Downtown Lenox by Evergreen Home
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Exterior

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (59)
"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Charming Apt in 18th c Berkshire Farmhouse

Charming Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (31)
"The space was cozy and clean and the owners were very easy to communicate with and knowledgeable about the area. The bathroom has very fun lights. "
The price is AED 533
AED 797 total
includes taxes & fees
23 Dec - 24 Dec
Charming Apt in 18th c Berkshire Farmhouse
Hip on Warren
Living area

Hip on Warren

10.0 out of 10, Exceptional, (8)
"Apartment is adorable and right on Warren that has everything you could want for a quick visit to upstate NY. Restaurants , stores of all kinds and great coffee shops and bars. "
The price is AED 1,010
AED 1,462 total
includes taxes & fees
23 Dec - 24 Dec
Hip on Warren
5 Bed / 3 bath Apt Near Jiminy Peak Berkshires
Kitchen comes fully stocked with all essentials. Gas stove, double side fridge, dishwasher, Keurig machine, etc.

5 Bed / 3 bath Apt Near Jiminy Peak Berkshires

10.0 out of 10, Exceptional, (1)
"We stayed here because we had Tanglewood tickets which turned out to be a great stay… It was a beautiful drive getting there and close enough to Tanglewood. Our host gave wonderful advice on where to eat and places to go. Thanks so much for sharing your place with us. Would absolutely consider going back "
5 Bed / 3 bath Apt Near Jiminy Peak Berkshires
Upstairs on Main
Exterior

Upstairs on Main

9.2 out of 10, Wonderful, (31)
"Check in was easy, beds are comfortable. I’m a big and tall guy, so only qualm I had was the small toilet, and low shower head. Aside from those, great stay!"
Upstairs on Main
Main Street Delight 1bedroom
Living area

Main Street Delight 1bedroom

10.0 out of 10, Exceptional, (18)
"The location was fantastic for our stay in the Berkshires. Walkable to many restaurants & shops. It was very well decorated & cozy. Very convenient being above a coffee shop, however not ideal if you enjoy sleeping in. We could hear the consistent squeaking of the coffee shop door as soon as it opened in the morning (~7:00 am) from the bedroom. However, good motivation to get up and enjoy the beautiful Berkshires!"
Main Street Delight 1bedroom
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Beautiful State of Art Kitchen Awaits in this spacious 900 Sq FT Suite

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

9.8 out of 10, Exceptional, (20)
"We had a lovely time at this large and welcoming condo. It was easy to find, had all the amenities we needed and was just the perfect place for an off-season get away. Would easily re-book at any time during the year. "
The price is AED 768
AED 1,406 total
includes taxes & fees
2 Jan - 3 January 2025
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Heart of Lenox!! - renovated downtown apartment
Private kitchen

Heart of Lenox!! - renovated downtown apartment

10.0 out of 10, Exceptional, (63)
"The bathroom was less than tidy and when I recall it was like that last time. Bathroom rug is dirty or just dirty looking. I advise property Meg to buy several Along with a Terry bath mat so you can cover it when using. No little extras like soap/shampoo are offered. I had My own. Overall the apartment is very cute would stay again. "
Heart of Lenox!! - renovated downtown apartment
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Super comfortable Mountain Decor

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

10.0 out of 10, Exceptional, (22)
"We loved our stay. The rental was as described. Jiminy Peak is great and everything is within walking distance. We had a great time !!!"
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Tiny House 2.5 hrs NYC and Boston Waterfront WIFI

Tiny House 2.5 hrs NYC and Boston Waterfront WIFI

9.6 out of 10, Exceptional, (23)
"We were treated with such kindness and understanding of our situation. We would gladly recommend Alisha to anyone wanting to stay at their property. In fact, we are going back in May. "
Tiny House 2.5 hrs NYC and Boston Waterfront WIFI
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Fully Redone Suite with master King Bed

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

10.0 out of 10, Exceptional, (2)
"Stayed one night at one of my favorite ski spots. Will be back again!"
The price is AED 713
AED 1,246 total
includes taxes & fees
25 Dec - 26 Dec
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Renovated Downtown 1bedroom
Living area

Renovated Downtown 1bedroom

10.0 out of 10, Exceptional, (21)
"Location, location, location. Great use of space in this nicely decorated, conveniently located apt. Steps away from restaurants and shopping. 7 minutes from Kripalu. Great communication from owner. Looking forward to next stay."
Renovated Downtown 1bedroom
Baldwin Hill Retreat Guest House
Living area

Baldwin Hill Retreat Guest House

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property and neighborhood were gorgeous! Walkable roads with low speed limits and a nearby park were major bonuses. Plenty of food options nearby, and downtown Great Barrington is only a short drive away. The house was super clean, gorgeously furnished, and very cozy. The beds and linens were very good quality and I had an incredibly restful stay. I will certainly be renting this spot for my next trip to the area! "
Baldwin Hill Retreat Guest House
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge
Living area

Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge

2.0 star property
10.0 out of 10, Exceptional, (3)
"Great location! The apartment was brand new. Well decorated and clean. "
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge
Downtown Hudson Apartment: Walk to Cafes & River!
Hudson Vacation Rental | 2BR | 1BA | 650 Sq Ft | Stairs Required

Downtown Hudson Apartment: Walk to Cafes & River!

10.0 out of 10, Exceptional, (2)
"Great little place! Well equipped with everything we needed. Would stay at again…easy for visiting family nearby."
Downtown Hudson Apartment: Walk to Cafes & River!
The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite

10.0 out of 10, Exceptional, (2)
"The motel was well equipped, clean, and comfortable. It was especially suited for my travel with my dog."
The price is AED 518
AED 633 total
includes taxes & fees
13 Jan - 14 January 2025
The Brooks Motel: Exceptional Suite
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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Other property types in West Stockbridge

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Breakfast Nook - wake up to the best sunshine ever!

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Wellspring by AvantStay | Indoor Pool + Views
Welcome!

Wellspring by AvantStay | Indoor Pool + Views

10.0 out of 10, Exceptional, (8)
"The location is absolutely beautiful, the pool was great, and there was plenty of room for everyone. This was our second time staying at this house and we will be back."
Wellspring by AvantStay | Indoor Pool + Views
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1750)
"Nice and quiet family get a way"
The price is AED 689
AED 792 total
includes taxes & fees
1 Jan - 2 January 2025
Vacation Village in the Berkshires
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.

Frequently asked questions

What's it like to stay at an apartment in West Stockbridge?
There are plenty of places to stay in West Stockbridge with 33 accommodations. Though there aren’t many apartments, we can help you search for accommodations with similar amenities. When you search on Expedia, you can filter by amenities you might find in an apartment like a kitchen. You can also search for similar properties such as vacation homes, condos, or cabins. While in the area, why not enjoy its gardens and visit its restaurants?
How do you know if an apartment is a good option for you?
An apartment features a kitchen for convenient meals, and is often more spacious than a traditional hotel room. Apartments are a good option for couples who want to live like locals, but also for families wanting the conveniences of home.
What's a favorite apartment I should consider for a stay in West Stockbridge?
Listed below are some of the top apartments in the area to choose from: Cozy Rustic Apt in 18th c Berkshire Farmhouse: Situated in Lanesborough, 15.7 mi/25.2 km from the heart of West Stockbridge. Includes fireplaces and sofa beds. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located 6.2 mi/10 km away in Lee. Private patios and fireplaces are included. Charming Apt in 18th c Berkshire Farmhouse: It’s situated in Lanesborough, 15.7 mi/25.2 km away. Includes fireplaces. Hip on Warren: 22.1 mi/35.6 km away in Hudson. Free WiFi and Smart TVs are included. Cozy Berkshires Vacation Rental Near Hiking!: Located in Chester, 20.2 mi/32.5 km from West Stockbridge. Includes sofa beds. Access to a game room is available on site.
What will the weather be like when I travel to West Stockbridge?
Weather is only one factor, but it can really affect your travel plans, especially if you are planning a longer stay in West Stockbridge. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in West Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What are the must-see places to visit in West Stockbridge?
West Stockbridge is known for its restaurants and gardens. Charles H. Baldwin & Sons and Hotchkiss Mobile Studio are a couple of family-friendly sights. While here, Ebenezer II Gifts and Antiques and Hoffman’s Pottery are other places worth a visit.
What's the best way to get to and around West Stockbridge?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 7.4 mi (11.9 km) away from the heart of the city. Otherwise, look for flights into Hudson, NY (HCC-Columbia County), which is 17.8 mi (28.7 km) away. If you’d like to explore around the area, you may want a rental car for your journey.