A nighttime view of a residential area with houses adorned with holiday lights.

Search Apartments in Stockbridge

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Stockbridge apartments

Desk, iron/ironing board, WiFi, bed sheets

1. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very good, (6 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is €179
includes taxes & fees
11 Aug - 12 Aug
The Brooks Motel: Exceptional Suite
Coffee/tea maker, fridge, microwave, oven

2. 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, (30 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.
The price is €288
includes taxes & fees
12 Aug - 13 Aug
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Desk, iron/ironing board, WiFi, bed sheets

3. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is €170
includes taxes & fees
11 Aug - 12 Aug
The Brooks Motel: Exceptional Suite
Gift shop

4. 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, (5 reviews)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
The price is €222
includes taxes & fees
12 Aug - 13 Aug
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Beach

5. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (4 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
The price is €237
includes taxes & fees
11 Aug - 12 Aug
Berkshires Apartment at the Stephentown Hotel
Pool

6. 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.
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Gift shop

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

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (13 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is €225
includes taxes & fees
11 Aug - 12 Aug
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Pool

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

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Hancock
9.8 out of 10, Exceptional, (25 reviews)
"We stayed here twice this season and it was wonderful. The unit was clean, conveniently located and was fully equipped with all the essentials, making our stay comfortable and seamless from start to finish. We will definitely be back!"
United States
Kristina L.
The price is €217
includes taxes & fees
11 Aug - 12 Aug
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Indoor pool, a heated pool

9. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Hancock
9.4 out of 10, Exceptional, (6 reviews)
"Convenience to slopes and restaurants really great….,had a nice stay"
United States
Thomas S.
The price is €217
includes taxes & fees
11 Aug - 12 Aug
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Pool

10. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Hancock
9.6 out of 10, Exceptional, (35 reviews)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
The price is €283
includes taxes & fees
11 Aug - 12 Aug
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Pool

11. Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
9.0 out of 10, Wonderful, (4 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
The price is €342
includes taxes & fees
9 Sept - 10 Sept
Hudson NY’S Country Serenity Guest Suite.
TV, fireplace, DVD player

12. Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views

Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
Hancock
8.0 out of 10, Very good, (1 review)
"I chose this place at the very last minute. It was all that I expected and wanted and more: two bedrooms with three beds, a comfortable living space, two full bathrooms, kitchen with all the basic necessities, TV in each bedroom and in the living room, a dining table and chairs, an outside porch with table, a big open space, and grill, easy parking and access, quiet, .and access to two pools. The place was well tended: clean, with towels and extras blankets ready. Howard, the owner, checked on...
United States
Cecilia S.
The price is €330
includes taxes & fees
11 Aug - 12 Aug
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
Beach

13. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
8.4 out of 10, Very good, (12 reviews)
"Great location and property. thank you"
United States
Christine P.
The price is €252
includes taxes & fees
24 Aug - 25 Aug
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Property grounds

14. 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.
The price is €217
includes taxes & fees
11 Aug - 12 Aug
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Pool

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

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Hancock
9.6 out of 10, Exceptional, (33 reviews)
"The suite was a great. Comfortable, clean and decorated very nicely. Bed was very comfortable with nice linens and pillows. "
United States
Eileen O.
The price is €217
includes taxes & fees
11 Aug - 12 Aug
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Indoor pool

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

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (22 reviews)
"Great skiing and proximity to mountain. Great for families"
United States
John F.
The price is €225
includes taxes & fees
11 Aug - 12 Aug
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Exterior

17. 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Hancock
8.8 out of 10, Excellent, (8 reviews)
"Everything was wonderful…"
United States
Alyne K.
The price is €217
includes taxes & fees
11 Aug - 12 Aug
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
TV, fireplace, DVD player, offices

18. Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
Hancock
9.6 out of 10, Exceptional, (4 reviews)
"Excellent instructions by the owner for the check in process, which was easy. The room was beautiful and very clean, and exactly as advertised. We would absolutely recommend and stay again!!"
United States
Chad J.
The price is €286
includes taxes & fees
11 Aug - 12 Aug
Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
Beach

19. 5 Bed / 3 bath Apt Near Jiminy Peak Berkshires

5 Bed / 3 bath Apt Near Jiminy Peak Berkshires
Stephentown
9.4 out of 10, Exceptional, (6 reviews)
"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 "
United States
Maureen O.
5 Bed / 3 bath Apt Near Jiminy Peak Berkshires
Interior

20. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Otis
The price is €293
includes taxes & fees
24 Aug - 25 Aug
Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Stockbridge Hotel Reviews

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"Just there one night, everyone on the property was very friendly and helpful. The room was very clean and beds were comfortable. Breakfast was as expected for this type of stay. Would definitely come again."
Craig 1-night trip
Posted 1 hour ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Find out more about Stockbridge

Stockbridge Apartments information

Number of reviews
Accommodation
 Apartments
Lowest Price
Highest Price

Frequently asked questions

What's it like to stay at an apartment in Stockbridge?
There are 5 apartments to choose from in Stockbridge for your stay. While visiting this relaxing area, you might want to enjoy its bars.
Are you considering apartments over traditional hotel rooms?
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 couples who want to stay away from the tourist areas.
What's the top apartment for my stay in Stockbridge?
Here are some of the more popular apartments in the area to choose from: Cozy 1-bedroom studio in serene Great Barrington with AC: Located 7 mi/11.3 km away in Great Barrington . Free WiFi, a balcony and a Smart TV are included . Access to on-site laundry facilities is available on site . Modern Copake Falls Getaway: It's situated in Copake Falls , 13.7 mi/22 km away. Includes a patio and a fireplace . Hotel-like Balcony Suite—View—Private Wing&Entry—Ensuite Bath—Walk to Town, Lake: 6 mi/9.7 km away in Great Barrington . Free WiFi, a balcony and a Smart TV are included .
How many apartments are there in Stockbridge?
Expedia has 5 apartments to book in Stockbridge.
What will the weather be like in Stockbridge?
Although 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 temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Stockbridge are January, March, February and November, with each month seeing an average of 18 cm 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 Berkshire Theatre Festival. While here, National Shrine of the Divine Mercy and Stockbridge Bowl 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 save you time when you get to your destination. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 9.6 mi (15.5 km) away. Otherwise, you can search for flights to 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.