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

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.2 out of 10, Wonderful, (12)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

10.0 out of 10, Exceptional, (1)
"The one-bedroom aparment is spacious, very clean, nice and funtional furniture and a perfectly well equipped kitchen area. Our 2 grandchildren had a fun time. And the apartament is footsteps from the ski lifts - a real treat! I highly recommend it!Ps. And the owner is always at hand, very helpful, and concerned that all is perfect for the guest's stay."
The price is SAR 589
SAR 1,101 total
includes taxes & fees
4 Feb - 5 Feb
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

10.0 out of 10, Exceptional, (5)
"Condo was conveniently located at the base of the mountain. Had everything you would need for a quick weekend getaway. Owner was available for any questions."
The price is SAR 589
SAR 1,101 total
includes taxes & fees
3 Feb - 4 Feb
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

10.0 out of 10, Exceptional, (4)
"Perfect place to stay for a quick ski trip. Host was super helpful & accommodating. Suite was comfortable & well-equipped. We’ll be back "
The price is SAR 589
SAR 1,101 total
includes taxes & fees
2 Feb - 3 Feb
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"Perfect location. Walking distance. Brand new apartment. "
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

9.6 out of 10, Exceptional, (30)
"Perfect 1 bedroom, ski in ski off , updated unit with great amenities! Owner super responsive and accommodating. Will definitely be back "
The price is SAR 589
SAR 1,101 total
includes taxes & fees
2 Feb - 3 Feb
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

The Penthouse, Downtown Lenox by Evergreen Home

10.0 out of 10, Exceptional, (7)
"This is the second year we had our girls weekend at the Penthouse and it did not disappoint. The place is updated, very clean, and in a great location! Only suggestion would to get a nice big sectional couch! We had 8 people and not enough comfy seating. But beautiful apartment!! "
The Penthouse, Downtown Lenox by Evergreen Home

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

2.0 star property
9.0 out of 10, Wonderful, (2)
"Our stay was excellent overall! We really admired the tidiness of the property. The ski trails were hit to. The only thing that brought this review down was that the T.V.’s in our room were not working but the stay was pretty good!"
Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!

Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts

10.0 out of 10, Exceptional, (1)
Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

9.8 out of 10, Exceptional, (23)
"Everything was great. Very clean unit and it def is a ski in/out. Plenty of space in bedrooms. Howard is easy to communicate with and a great host. Truly a gem in jimminy peak. "
The price is SAR 784
SAR 1,436 total
includes taxes & fees
2 Feb - 3 Feb
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Modern Copake Falls Getaway

9.6 out of 10, Exceptional, (29)
"Unbeatable accommodations, especially for the price. Would stay again, gorgeous sunrise and sunset, very peaceful. Wish I could live there part time!"
Modern Copake Falls Getaway

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

9.8 out of 10, Exceptional, (17)
"The condo was clean and well located for easy access to the mountain. We were there for tri-state races and having easy acass to the mountain was exactly what we needed for a fun weekend. We would stay here again."
The price is SAR 589
SAR 1,101 total
includes taxes & fees
2 Feb - 3 Feb
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

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 SAR 589
SAR 1,101 total
includes taxes & fees
2 Feb - 3 Feb
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

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

Renovated Downtown 1bedroom

10.0 out of 10, Exceptional, (22)
"We’ve always had a great experience with Downtown Upstairs in Lenox and this was no exception. Easy access to the downtown stores and restaurants with the comfort of a nice, clean, well furnished apartment. "
Renovated Downtown 1bedroom

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

9.4 out of 10, Exceptional, (60)
"The property was fine for our purposes of visiting family. If we needed to cook, it would have been quite difficult, though not totally impossible. The furniture was comfortable and the rooms, except the kitchen, had plenty of space. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Lovely bright apartment in pastoral shaker barn

10.0 out of 10, Exceptional, (2)
"We traveled from Arizona for a class reunion and stayed in apartment. The property was clean and well appointed. We were able to host a dinner with four family members we had not seen in years! Another highlight was sitting outside by the fire pit in the evening. The property host, Michelle, provided excellent check in instructions and answered any questions very promptly. This property worked out very well for us, but if you have an issue with stairs you might want to check out the other...
Lovely bright apartment in pastoral shaker barn

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 SAR 589
SAR 1,101 total
includes taxes & fees
2 Feb - 3 Feb
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

51 Church Street, Lenox MA - One Bedroom Unit

10.0 out of 10, Exceptional, (24)
"Lovely apartment in a great location "
51 Church Street, Lenox MA - One Bedroom Unit

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
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

Historic Rectory Retreat in Stockbridge – Getaway for 8-12 Guests

10.0 out of 10, Exceptional, (8)
"We could not have been happier. The house was walking distance to all shops, restaurants and attractions of the town of Stockbridge. House was large enough to comfortably accommodate 9 adults. Thoroughly enjoyed "Christmas in Stockbridge"."
Historic Rectory Retreat in Stockbridge – Getaway for 8-12 Guests

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1759)
"Great place "
The price is SAR 563
SAR 655 total
includes taxes & fees
3 Feb - 4 Feb
Vacation Village in the Berkshires

The Ponds at Foxhollow by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is SAR 867
SAR 969 total
includes taxes & fees
14 Feb - 15 Feb
The Ponds at Foxhollow by Capital Vacations
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 43 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?
Here are some of the favorite apartments in the area to choose from: Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge: Situated in Stockbridge, 0.6 mi/1 km from the heart of Stockbridge. 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor: Located 18.5 mi/29.9 km away in Hancock. Amenities include sofa beds. A fitness center and an indoor pool are on site. Amazing 2-bedroom apartment sunny and quiet in Great Barrington: It’s situated in Great Barrington, 6.6 mi/10.7 km away. Includes free WiFi, separate dining areas, and Smart TVs. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor: Located 18.5 mi/29.9 km away in Hancock. Amenities include sofa beds. A fitness center and a spa tub are on site. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone: Located in Hancock, 18.6 mi/29.9 km from Stockbridge. Includes sofa beds. A fitness center and an indoor pool are on site.
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 Mission House and Norman Rockwell Museum. While here, National Shrine of the Divine Mercy and Frelinghuysen Morris House and Studio 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.