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Compare 79 Apartments in 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, (7)
"The place was what we imagined- the rooms were great size and the decor was homey with links of beautiful pottery. It was nice to have seasoning and tea in house. It took a while to figure out the water temp in shower. Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Charming Apartment In Berkshire Victorian Home
Exterior
Charming Apartment In Berkshire Victorian Home
8.0 out of 10, Very Good, (6)
"This adorable place is central to Pittsfield and made it really easy for my daughter and I go get where we needed to be. It’s a clean, great space. We’ll definitely be back!"
Charming Apartment In Berkshire Victorian Home
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, (19)
"the owner was very nice and helpfull"
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
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 584
AED 715 total
includes taxes & fees
11 Nov - 12 Nov
The Brooks Motel: Exceptional Suite
Garfield House Studio at 208
Exterior
Garfield House Studio at 208
9.6 out of 10, Exceptional, (28)
"Zero complaints. Perfect location"
Garfield House Studio at 208
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 793 total
includes taxes & fees
6 Nov - 7 Nov
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Private apartment in beautiful country barn
Living area
Private apartment in beautiful country barn
10.0 out of 10, Exceptional, (18)
"Great farmhouse in the Berkshires. Location is out of the way without being out of the way. Communications with the host is great. Very accommodating."
Private apartment in beautiful country barn
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
9.2 out of 10, Wonderful, (9)
"Such a awesome facility! Love the room, the Jiminy property is very cool and you don’t even need to leave to go anywhere else because there is so much to do here. Stay."
The price is AED 382
AED 831 total
includes taxes & fees
6 Nov - 7 Nov
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
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
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
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Comfortable Living Room with Pullout Queen Sofa Bed and Smart TV with Full DVD Library and Board Game library for those nights in.
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
9.6 out of 10, Exceptional, (29)
"Was in town for my HS reunion and loved my stay! Great location and amenities and the condo itself is super cute."
The price is AED 382
AED 831 total
includes taxes & fees
6 Nov - 7 Nov
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
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 382
AED 831 total
includes taxes & fees
6 Nov - 7 Nov
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
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
Gateway to the Berkshires - Renovated downtown apartment
Room
Gateway to the Berkshires - Renovated downtown apartment
10.0 out of 10, Exceptional, (7)
"Thanks, Emmy, for a great visit. The apartment was exactly what we hoped for, clean and convenient to downtown and to all things in the Berkshires. We explored and relaxed and thoroughly enjoyed our getaway over a beautiful October weekend. I'd recommend the apartment to anyone who wants that in-town setting and wishes to explore all that the area has to offer. Great host, thank you!"
Gateway to the Berkshires - Renovated downtown apartment
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
Exterior
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
2.0 star property
10.0 out of 10, Exceptional, (1)
"This location was perfect for hiking the AT. The trail is only a few feet from the front door. The backyard is very nice, and they had chairs and tables to sit out. The apartment was a nice size for two people. There was no tv, so we used our computer. The kitchen was great to have since we didn't plan on eating out every night. There are plenty of restaurants in the area. The hosts were great and very responsive. The fall colors made the trip extra special."
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
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 Berkshires Vacation Rental Near Hiking!
Chester Vacation Rental | 2BR | 1BA | 2,000 Sq Ft | Stairs Required
Cozy Berkshires Vacation Rental Near Hiking!
10.0 out of 10, Exceptional, (1)
"The stay at the property was enjoyable. The space was large, spacious and very clean. Two people were able to stay quite comfortably."
Cozy Berkshires Vacation Rental Near Hiking!
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, (57)
"Excellent location in Lee allowed us to visit many adjacent towns and attractions in the Berkshires. Very responsive host."
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, (29)
"Some friends and I were in town for a wedding and were just staying the night and the property was perfect for what we needed! It was very clean and well-maintained. The only minor thing was the building is close to the road and we could hear some traffic at night, but it wasn’t too disruptive. We really enjoyed our stay, thank you!"
The price is AED 533
AED 793 total
includes taxes & fees
6 Nov - 7 Nov
Charming Apt in 18th c Berkshire Farmhouse
Apartment in Gorgeous Stonybrook Farm
Apartment in Gorgeous Stonybrook Farm
9.4 out of 10, Exceptional, (44)
"This was a beautifully appointed property on an estate overlooking a pond. The apartment was spotless and the caretaker was most helpful when we needed anything. The rooms were well supplied and perfect for us. Thank you for letting us experience the quintessence of the Berkshires."
Apartment in Gorgeous Stonybrook Farm
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 Stockbridge

Find your Sanctuary at The Rectory at Stockbridge
Exterior
Find your Sanctuary at The Rectory at Stockbridge
10.0 out of 10, Exceptional, (6)
"The host, Samantha, was ideal! She was communicative, accomodating, and attentive. The place was perfect, right in the heart of town"
The price is AED 2,387
AED 3,939 total
includes taxes & fees
6 Nov - 7 Nov
Find your Sanctuary at The Rectory at Stockbridge
Vacation Village in the Berkshires
Lobby
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1743)
"The suite was clean, comfortable, and ready when I arrived."
The price is AED 620
AED 717 total
includes taxes & fees
6 Nov - 7 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (914)
"Nice fall view"
The price is AED 547
AED 600 total
includes taxes & fees
6 Nov - 7 Nov
Jiminy Peak Mountain Resort
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 Stockbridge?
There are plenty of places to stay in Stockbridge with 42 hotels and other lodging accommodations. Though there aren’t many apartments, we can help you search for similar accommodations. When you search for a place to stay on Expedia, you can use the filters to search for conveniences you might find in an apartment such as a kitchen. You can also filter by similar property types like vacation homes, condos, or cabins. While visiting this relaxing area, you might want to enjoy its bars.
Are you thinking about an apartment instead of a traditional hotel?
An apartment is often more spacious than a traditional hotel room and comes with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home but also for solo travelers who want to stay in at night and plan out their next day.
What's the top apartment for my stay in Stockbridge?
Below are some of the more popular apartments in the area to choose from: New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.: Located 9 mi/14.4 km away in Richmond. Cozy Berkshires Vacation Rental Near Hiking!: Located 17.4 mi/28.1 km away in Chester. Amenities include sofa beds. Access to a game room is available on site. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: It’s located in Lee, 3.8 mi/6.2 km from Stockbridge. Includes private patios and fireplaces.
What will the weather be like in Stockbridge?
Though weather is just one factor, it can really affect your travel plans, especially if you are planning a longer stay in 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 Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What should I see and do in Stockbridge?
Stockbridge is known for its bars. Enjoy the outdoors at Naumkeag Museum and Berkshire Botanical Garden, or simply take in cultural attractions like Norman Rockwell Museum and Mission House. While here, National Shrine of the Divine Mercy and Beartown State Forest are other places worth a visit.
What's the best way to get to and around Stockbridge?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 9.6 mi (15.5 km) from the city center. Otherwise, look for flights into Hudson, NY (HCC-Columbia County), which is 20 mi (32.3 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.