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Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Apartments in Stockbridge

Fridge, microwave, oven, stovetop
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse

Lanesborough
9.6 out of 10, Exceptional, (67)
"Great value, so much better than all the touristy motels in the area!"
United States
Chris G.
The price is AED 496
AED 763 total
includes taxes & fees
21 Nov - 22 Nov
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Exterior
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, (8)
"We had a wonderful 3 day weekend! Perfect location for families."
United States
Eric B.
The price is AED 419
AED 907 total
includes taxes & fees
24 Nov - 25 Nov
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Exterior
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, (5)
"We had a wonderful stay in our fun, pirate themed suite. Which is really what caught our attention in making our reservation. It was so thoughtfully decorated, and suited the theme, while still being a comfortable place to enjoy being in. Everything was in wonderful condition, and had all the amenities we needed. Our host, Howie, was incredibly attentive, personable, and made sure we were taken care of. I was very disorganized, and he went out of his way to get me all the information we needed...
United States
Karen
The price is AED 419
AED 907 total
includes taxes & fees
24 Nov - 25 Nov
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Indoor pool
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, (3)
"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 AED 419
AED 907 total
includes taxes & fees
24 Nov - 25 Nov
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Exterior
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, (16)
"Nice Place"
United States
Tom C.
The price is AED 419
AED 907 total
includes taxes & fees
24 Nov - 25 Nov
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Fridge, microwave, oven, stovetop
Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel

Stephentown
10.0 out of 10, Exceptional, (3)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is AED 354
AED 788 total
includes taxes & fees
23 Nov - 24 Nov
Berkshires Apartment at the Stephentown Hotel
Exterior
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, (20)
"Great place to spend the new years holiday! Perfect location for skiing!"
United States
Alexandra D.
The price is AED 419
AED 907 total
includes taxes & fees
24 Nov - 25 Nov
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Exterior
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, (30)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
The price is AED 584
AED 1,198 total
includes taxes & fees
24 Nov - 25 Nov
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
TV, offices
The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite

Hillsdale
9.2 out of 10, Wonderful, (5)
"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 584
AED 740 total
includes taxes & fees
21 Nov - 22 Nov
The Brooks Motel: Exceptional Suite
1 bedroom, WiFi, bed sheets
Charming Apt in 18th c Berkshire Farmhouse

Charming Apt in 18th c Berkshire Farmhouse

Lanesborough
9.4 out of 10, Exceptional, (39)
"It’s a nice comfortable apartment with a good kitchen. We were traveling to see a concert and some art at Mass MOCA. Patrick is a friendly and welcoming host."
United States
Roy
The price is AED 496
AED 746 total
includes taxes & fees
21 Nov - 22 Nov
Charming Apt in 18th c Berkshire Farmhouse
Pool
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Hancock
10.0 out of 10, Exceptional, (3)
"Great room decorations, travel with two kids they have a great time playing video games"
United States
Andres
The price is AED 419
AED 907 total
includes taxes & fees
24 Nov - 25 Nov
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Exterior
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)
"Great location. Very nice vacation. Would def go again. "
United States
Elizabeth M.
The price is AED 419
AED 907 total
includes taxes & fees
24 Nov - 25 Nov
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Exterior
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)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
The price is AED 419
AED 907 total
includes taxes & fees
24 Nov - 25 Nov
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Indoor pool
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, (18)
"We enjoyed our stay in this adorable Disney Themed condo. The attention to detail in the theming was fantastic and the condo was perfect for our February Vacation ski trip."
United States
Allison V.
The price is AED 419
AED 907 total
includes taxes & fees
24 Nov - 25 Nov
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Property grounds
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
9.2 out of 10, Wonderful, (12)
"We enjoyed our stay. We would definitely stay here again in the future."
United States
Scott
The price is AED 419
AED 907 total
includes taxes & fees
24 Nov - 25 Nov
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Exterior
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
10.0 out of 10, Exceptional, (23)
"This property is spacious, clean and well- appointed. I would stay here again!"
United States
Amanda M.
The price is AED 419
AED 907 total
includes taxes & fees
24 Nov - 25 Nov
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Exterior
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, (30)
"Was in town for my HS reunion and loved my stay! Great location and amenities and the condo itself is super cute."
United States
Maura S.
The price is AED 419
AED 907 total
includes taxes & fees
24 Nov - 25 Nov
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Fridge, microwave, oven, stovetop
2 Bed Berkshire Getaway @ Stephentown Hotel

2 Bed Berkshire Getaway @ Stephentown Hotel

Stephentown
10.0 out of 10, Exceptional, (5)
"This place is amazing! It is so clean and updated with lots of amenities! Lots of arcade games in the apartment thatthe whole family enjoyed! It's a quick trip to jimney peak to ski it's just down the road. Great restaurants nearby. Definitely recommend this place."
United States
elizabeth r.
The price is AED 511
AED 974 total
includes taxes & fees
22 Nov - 23 Nov
2 Bed Berkshire Getaway @ Stephentown Hotel
Dining
Bright Boho Apt in 18th c Berkshire Farmhouse

Bright Boho Apt in 18th c Berkshire Farmhouse

Lanesborough
9.0 out of 10, Wonderful, (22)
"I loved staying here the weekend with my friends, the owner Patrick was so accommodating and helpful!"
United States
Mckenna d.
The price is AED 533
AED 808 total
includes taxes & fees
27 Nov - 28 Nov
Bright Boho Apt in 18th c Berkshire Farmhouse
Fridge, microwave, oven, stovetop
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)
"Great location and property. thank you"
United States
Christine P.
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Clean, comfortable facilty"
Julie 1-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Frequently asked questions

What's it like to stay at an apartment in Stockbridge?
There are plenty of places to stay in Stockbridge with 51 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: Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located in Lee, 3.8 mi/6.2 km from the heart of Stockbridge. Includes private patios and fireplaces. Access to onsite laundry facilities is available on site. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- 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. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton: Located in Dalton, 15.6 mi/25.1 km away. Includes free WiFi, separate dining areas, and Smart TVs. Access to onsite laundry facilities is available on site. Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4: Located 18.5 mi/29.9 km away in Hancock. Amenities include fireplaces. A fitness center and a hot tub are on site. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous: Located in Hancock, 18.6 mi/30 km from Stockbridge. Includes fireplaces and sofa beds. A fitness center and onsite laundry facilities 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 Norman Rockwell Museum and Frelinghuysen Morris House and Studio. While here, National Shrine of the Divine Mercy and Housatonic River 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.