A river surrounded by autumn-colored trees and a forested hill.

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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
9.0 out of 10, Wonderful, (9 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 AED 364
AED 550 total
includes taxes & fees
29 Oct - 30 Oct
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, (6 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 AED 735
AED 1,206 total
includes taxes & fees
3 Nov - 4 Nov
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A covered outdoor seating area with two chairs and a view of a grassy landscape.

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 AED 826
AED 1,141 total
includes taxes & fees
21 Nov - 22 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 AED 551
AED 699 total
includes taxes & fees
15 Nov - 16 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, (34 reviews)
"We were on a girls backpacking trip and this was the perfect location right off the trail to clean up, get some great rest and grab dinner. The people are so friendly in Dalton and this place had everything we needed!"
United States
Allie T.
The price is AED 545
AED 1,327 total
includes taxes & fees
26 Oct - 27 Oct
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 AED 343
AED 855 total
includes taxes & fees
25 Oct - 26 Oct
Berkshires Apartment at the Stephentown Hotel
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

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 AED 397
AED 878 total
includes taxes & fees
27 Oct - 28 Oct
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A snow-covered outdoor area with a fire pit, tables, and chairs.

8. 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.
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
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 AED 397
AED 878 total
includes taxes & fees
27 Oct - 28 Oct
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

10. 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 AED 602
AED 761 total
includes taxes & fees
22 Nov - 23 Nov
The Brooks Motel: Exceptional Suite
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

11. 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 AED 397
AED 878 total
includes taxes & fees
27 Oct - 28 Oct
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

12. 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, (18 reviews)
"Nice Place"
United States
Tom C.
The price is AED 397
AED 878 total
includes taxes & fees
27 Oct - 28 Oct
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A poolside dining area with a table set for a meal, surrounded by a pool and greenery.

13. 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 AED 731
AED 1,399 total
includes taxes & fees
27 Oct - 28 Oct
Hudson NY’S Country Serenity Guest Suite.
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

14. 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.
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
A wooden deck with outdoor furniture, a glass door leading to a view of a grassy area with trees.

15. 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 AED 580
AED 1,198 total
includes taxes & fees
25 Oct - 26 Oct
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
A bedroom with a large bed, a nightstand, an air conditioning unit, and a view through the window.

16. 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 AED 444
AED 1,022 total
includes taxes & fees
25 Oct - 26 Oct
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
A sign for The Stephentown Hotel with a depiction of a red building and mountains.

17. 2 Bed Berkshire Getaway @ Stephentown Hotel

2 Bed Berkshire Getaway @ Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (7 reviews)
"The apartment was super clean, super comfortable, and so close to my family get together. I will definitely be back in September. Dillon was quick to respond and everything was exceptional."
United States
Sandra V.
2 Bed Berkshire Getaway @ Stephentown Hotel
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

18. 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 AED 591
AED 1,219 total
includes taxes & fees
27 Oct - 28 Oct
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
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.
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Four people seated at a table with food and drinks, wearing winter sports helmets.

20. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Hancock
9.8 out of 10, Exceptional, (9 reviews)
"A great, comfy suite! We had a great stay! "
United States
Wendy D.
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
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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Top Stockbridge Hotel Reviews

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Unique and very thoughtfully thought through. Welcome bottle of wine, welcome drink, and breakfast were great! Wish the bar was open later and breakfast started earlier, but this is a minor thing. Would definitely stay there again."
Jeffrey 1-night trip
Posted 1 hour ago
The Cornell Inn, Lenox & The Berkshires

Frequently asked questions

What's it like to stay at an apartment in Stockbridge?
You'll find 5 apartments to choose from in Stockbridge for your vacation. 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: 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, private balconies, and Smart TVs. Access to onsite 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 private patios. Access to onsite 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, separate dining areas, and Smart TVs. Access to onsite 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, private balconies, and Smart TVs. Access to onsite 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?
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 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 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.