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Apartments in Stockbridge for Rent

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Our top choices for Stockbridge apartments

Dining
Charming Apt in 18th c Berkshire Farmhouse

Charming Apt in 18th c Berkshire Farmhouse

Charming Apt in 18th c Berkshire Farmhouse
Lanesborough
9.4 out of 10, Exceptional, (40)
"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
$188 nightly
The price is $206
Dec 23 - Dec 24
Total with taxes and fees
Charming 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

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.
$290 nightly
The price is $324
Dec 23 - Dec 24
Total with taxes and fees
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Indoor pool, a heated pool
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

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.
$290 nightly
The price is $324
Dec 23 - Dec 24
Total with taxes and fees
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Gift shop
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

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.
$281 nightly
The price is $314
Dec 23 - Dec 24
Total with taxes and fees
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Beach
Berkshires Apartment at the Stephentown Hotel

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.
$213 nightly
The price is $227
Dec 23 - Dec 24
Total with taxes and fees
Berkshires Apartment at the Stephentown Hotel
Pool
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

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.
$290 nightly
The price is $324
Dec 23 - Dec 24
Total with taxes and fees
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
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

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.
$290 nightly
The price is $324
Dec 23 - Dec 24
Total with taxes and fees
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Desk, iron/ironing board, WiFi, bed sheets
The Brooks Motel: Exceptional Suite

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.
$180 nightly
The price is $202
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Brooks Motel: Exceptional Suite
WiFi, bed sheets
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse
Lanesborough
9.6 out of 10, Exceptional, (67)
"We had a lovely stay! The studio was comfortable, clean, and just what we needed. Our hosts were friendly and helpful!"
United States
Janice L.
$188 nightly
The price is $206
Dec 23 - Dec 24
Total with taxes and fees
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Dining
Bright Boho Apt in 18th c Berkshire Farmhouse

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.
$199 nightly
The price is $219
Dec 23 - Dec 24
Total with taxes and fees
Bright Boho Apt in 18th c Berkshire Farmhouse
Smart TV, fireplace
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Great Barrington
$350 nightly
The price is $391
Dec 23 - Dec 24
Total with taxes and fees
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Pool
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

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.
$363 nightly
The price is $405
Jan 15 - Jan 16, 2026
Total with taxes and fees
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Exterior
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

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, (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."
United States
Antonio S.
$369 nightly
The price is $412
Dec 24 - Dec 25
Total with taxes and fees
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Outdoor dining
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

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
$369 nightly
The price is $412
Dec 24 - Dec 25
Total with taxes and fees
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Beach
2 Bed Berkshire Apt minutes to Jiminy Peak Ski

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.
$229 nightly
The price is $244
Dec 23 - Dec 24
Total with taxes and fees
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
1 bedroom, iron/ironing board, WiFi, bed sheets
Ski On Off Disney Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshi

Ski On Off Disney Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshi

Ski On Off Disney Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshi
Hancock
10.0 out of 10, Exceptional, (1)
"Great!"
United States
Susan M.
$290 nightly
The price is $324
Dec 23 - Dec 24
Total with taxes and fees
Ski On Off Disney Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshi
Exterior
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

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Hancock
9.8 out of 10, Exceptional, (7)
"Everything was wonderful…"
United States
Alyne K.
$249 nightly
The price is $278
Dec 23 - Dec 24
Total with taxes and fees
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Desk, iron/ironing board, WiFi, bed sheets
The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.0 out of 10, Good, (4)
"Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor."
United States
John P.
$179 nightly
The price is $200
Dec 23 - Dec 24
Total with taxes and fees
The Brooks Motel: Exceptional Suite
Property grounds
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

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)
"It was great experience and we loved the ammenities."
United States
Carrie C.
$290 nightly
The price is $324
Dec 23 - Dec 24
Total with taxes and fees
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Property grounds
2 Bed Berkshire Getaway @ Stephentown Hotel

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.
$301 nightly
The price is $320
Dec 30 - Dec 31
Total with taxes and fees
2 Bed Berkshire Getaway @ Stephentown Hotel
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 & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"While waiting for our vallet car due to construction. The hotel staff were engaging and had personal conversations with us. Rooms were good and all staff treated us exceptional. Give them an atta boy on proformance"
Nathan 1-night trip
Posted 7 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Find out more about Stockbridge

Stockbridge Apartments information

Number of reviews
235
Accommodation
95 Apartments
Lowest Price
$200
Highest Price
$412

Frequently asked questions

What's it like to stay at an apartment in Stockbridge?
There are plenty of places to stay in Stockbridge with 46 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: Amazing 2-bedroom apartment sunny and quiet in Great Barrington: Located in Great Barrington, 6.6 mi/10.7 km from the heart of Stockbridge. Includes free WiFi, separate dining areas, and Smart TVs. Access to onsite laundry facilities is available on site. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous: Located 18.6 mi/30 km away in Hancock. Fireplaces and sofa beds are included. A fitness center and onsite laundry facilities are on site. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn: Located in Hancock, 18.6 mi/29.9 km away. Includes sofa beds. A fitness center and onsite laundry facilities are on site. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located 3.8 mi/6.2 km away in Lee. Private patios and fireplaces are included. Access to onsite laundry facilities is available on site. Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4: Located in Hancock, 18.5 mi/29.9 km from Stockbridge. Includes fireplaces. A fitness center and a hot tub 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 Mission House. 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.

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