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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Stockbridge apartments

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.8 out of 10, Excellent, (10 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is £80
includes taxes & fees
11 Nov - 12 Nov
Cozy 1-bedroom studio in serene Great Barrington with AC
A sandy beach with a lake and forest in the background.

2. 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, (7 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is £243
includes taxes & fees
9 Nov - 10 Nov
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A modern kitchen with a dining area, built-in shelves, and a large window.

3. 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
The price is £220
includes taxes & fees
16 Nov - 17 Nov
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

4. 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 £161
includes taxes & fees
17 Nov - 18 Nov
The Brooks Motel: Exceptional Suite
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

5. 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, (35 reviews)
"Very smooth process for check in and directions. Well provisioned, super clean rooms. Really enjoyed learning about Dalton. And so many sights nearby we love!"
United States
Marcia O.
The price is £225
includes taxes & fees
10 Nov - 11 Nov
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

6. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (5 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 £169
includes taxes & fees
9 Nov - 10 Nov
Berkshires Apartment at the Stephentown Hotel
A cozy living room with a large window, wooden walls, and a television.

7. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is £170
includes taxes & fees
9 Nov - 10 Nov
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A bedroom with a wooden bed frame, a large window, and a painting of mountains on the wall.

8. 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 £170
includes taxes & fees
8 Nov - 9 Nov
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

9. 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
The price is £170
includes taxes & fees
9 Nov - 10 Nov
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

10. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (19 reviews)
"It's super well located, with a view of the hills from the picture window. Everything is comfortable, everything worked, and host's communication was excellent. Highly recommended."
United States
David
The price is £170
includes taxes & fees
10 Nov - 11 Nov
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A rustic wooden interior with shelves stocked with various products, a 'Tree-Free' sign, and a section with bottled beverages.

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

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
The price is £170
includes taxes & fees
9 Nov - 10 Nov
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

12. 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 £170
includes taxes & fees
8 Nov - 9 Nov
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
A row of multi-story buildings with a uniform architectural style, likely a hotel or resort, set against a backdrop of green hills and trees.

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

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (2 reviews)
"Great place, everything was so easy!!"
United States
Dana
The price is £170
includes taxes & fees
9 Nov - 10 Nov
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

14. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very good, (8 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 £154
includes taxes & fees
6 Nov - 7 Nov
The Brooks Motel: Exceptional Suite
A poolside dining area with a table set for a meal, surrounded by a pool and greenery.

15. Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
9.4 out of 10, Exceptional, (6 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
The price is £272
includes taxes & fees
8 Nov - 9 Nov
Hudson NY’S Country Serenity Guest Suite.
A wooden deck with outdoor furniture, a glass door leading to a view of a grassy area with trees.

16. 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 £228
includes taxes & fees
16 Nov - 17 Nov
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

17. 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)
"We really enjoyed our stay it was a very nice place for a family."
United States
Shmaya G.
The price is £233
includes taxes & fees
9 Nov - 10 Nov
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
A bedroom with a large bed, a nightstand, an air conditioning unit, and a view through the window.

18. 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 £205
includes taxes & fees
8 Nov - 9 Nov
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

19. Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Hancock
9.8 out of 10, Exceptional, (21 reviews)
"Great location! "
United States
shannon m.
The price is £170
includes taxes & fees
8 Nov - 9 Nov
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

20. 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 £170
includes taxes & fees
8 Nov - 9 Nov
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
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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Learn more about Stockbridge

Norman Rockwell's Museum showcases the artist's iconic paintings of small-town American life in his former studio. Stroll down Main Street's historic district before hiking Monument Mountain for views that inspired Nathaniel Hawthorne's literary works.

See all hotels in Stockbridge
A stone staircase leading up to a blue arched entrance, surrounded by lush greenery and birch trees.

Top reviews in Stockbridge

Front of property
The Inn at Stockbridge

The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge

10/10 Excellent

Our room was very clean and comfortable - exactly what we needed to rest well. Breakfast was excellent and we felt well taken care of. We are grateful for the friendly and welcoming hosts and their staff who listened to every need and graciously provided for us. We’ll definitely return for another stay when we’re in the area.
United Kingdom
Michele
Reviewed August 3, 2026
The Inn at Stockbridge

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?

Below are some of the more popular apartments in the area to choose from: Cozy 1-bedroom studio in serene Great Barrington with AC: Located in Great Barrington , 7 mi/11.3 km from the heart of Stockbridge. Includes free WiFi, a balcony and a Smart TV . Access to on-site laundry facilities is available on site . Cozy 1-bedroom apartment in old farm house in historic South Lee: Located 2.5 mi/4 km away in South Lee . Amenities include a patio . Access to on-site laundry facilities is available on site . Amazing 2-bedroom apartment sunny and quiet in Great Barrington : Located in Great Barrington , 6.6 mi/10.7 km away. Includes free WiFi, a dining area and a Smart TV . Access to on-site laundry facilities is available on site . Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake: Located in Great Barrington , 6 mi/9.7 km from Stockbridge. Includes free WiFi, a balcony and a Smart TV . Access to on-site laundry facilities is available on site .

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.