Stockbridge Vacation Rentals

Search over 1 million properties and 550 airlines worldwide.

Members save 10% more on select hotels, cars, activities and vacation rentals. Sign up.

Most hotels are fully refundable. Because flexibility matters.

Vacation Rentals in Stockbridge

Cozy Stockbridge Cabin - Walk to Beach & Lake!

Cozy Stockbridge Cabin - Walk to Beach & Lake!

Stockbridge, MA
Situated in Stockbridge, this cabin is 2.2 mi (3.5 km) from Naumkeag and 2.7 mi (4.4 km) from Tanglewood Music Center. Berkshire Botanical Garden and National ...
4/5Very Good! (2 reviews)
Very cozy getaway
"Perfect getaway. Easy access to lake. 10-15 min by car to nice easy/intermediate grade hikes."

Reviewed on Sep 5, 2020

Cozy Stockbridge Cabin - Walk to Beach & Lake!
General Williams Estate House Lenox/Stockbridge

General Williams Estate House Lenox/Stockbridge

Stockbridge, MA
This family-friendly Stockbridge vacation home is within 3 mi (5 km) of Berkshire Theatre Festival, Berkshire Botanical Garden, and Greenock Country Club. Housatonic ...
4.8/5Exceptional! (70 reviews)
Amazing Stay
"Cannot say enough good things about this home. Fantastic location, very clean and lots of space to spread out for activities. It was our groups first time out in the Berkshires and can’t wait to go back for another visit. Thank you for everything!"

Reviewed on Sep 15, 2021

General Williams Estate House Lenox/Stockbridge
Artist's Cottage on the Lake Mahkeenac

Artist's Cottage on the Lake Mahkeenac

Stockbridge, MA
Situated on a river, this historic cabin is 2.1 mi (3.3 km) from Frelinghuysen Morris House and Studio and 2.4 mi (3.8 km) from Tanglewood Music Center. The ...
5/5Exceptional! (5 reviews)
Rustic , clean Berkshire cabin.
"The home is rustic, but very clean. We enjoyed our stay and we were happy with with our choice of location and the home. The owner was extremely accommodating and easy to communicate with. Thanks so much!"

Reviewed on Aug 27, 2021

Artist's Cottage on the Lake Mahkeenac
You could be seeing lower prices

You could be seeing lower prices

With member prices, you could save 10% or more right now on thousands of properties.
Stockbridge Cottage minutes from downtown Lenox

Stockbridge Cottage minutes from downtown Lenox

Stockbridge, MA
This family-friendly Stockbridge cottage is located on a lake, within 3 mi (5 km) of Frelinghuysen Morris House and Studio and Tanglewood Music Center. Berkshire ...
5/5Exceptional! (5 reviews)
Great stay
"We had a great stay. House is lovely and well-equipped, and the location was perfect for our family. Hopefully we’ll be back!"

Reviewed on Aug 29, 2021

Stockbridge Cottage minutes from downtown Lenox
Completely Renovated Historic Home in the Heart of the Berkshires

Completely Renovated Historic Home in the Heart of the Berkshires

Stockbridge, MA
Situated in Stockbridge, this vacation home is within a 10-minute walk of Housatonic River and Chesterwood. Norman Rockwell Museum and Berkshire Botanical Garden ...
5/5Exceptional! (11 reviews)
Loved this home!
"We really enjoyed our too short stay. The home had all the amenities and comfort needed for a wonderful weekend. We will definitely be back!"

Reviewed on Jan 22, 2020

Completely Renovated Historic Home in the Heart of the Berkshires
"Too Good" AKA 2 Goodrich St.

"Too Good" AKA 2 Goodrich St.

Stockbridge, MA
Situated in Stockbridge, this vacation home is within a 15-minute walk of Housatonic River and Mission House. Berkshire Theatre Festival and Naumkeag are also ...
4.9/5Exceptional! (32 reviews)
Family Reunion
"Great getaway for a family reunion. 1/2 mile from town. Private, expansive backyard. Very well furnished. We were greeted with kitchen provisions - fruit, snacks, coffee, etc. felt very welcomed."

Reviewed on Jun 29, 2021

"Too Good" AKA 2 Goodrich St.
A Grand Estate in Historic Stockbridge

A Grand Estate in Historic Stockbridge

Stockbridge, MA
This family-friendly Stockbridge vacation home is located on the waterfront, just steps from Housatonic River and Mission House. Berkshire Theatre Festival and ...
4.9/5Exceptional! (43 reviews)
Massachusetts
"George and Caitlin were great host. Very helpful and accommodating. Would definitely return."

Reviewed on Sep 12, 2021

A Grand Estate in Historic Stockbridge
Great house in Stockbridge

Great house in Stockbridge

Stockbridge, MA
Situated in Stockbridge, this vacation home is within a 10-minute walk of Housatonic River and Mission House. Naumkeag and Berkshire Theatre Festival are also ...
Great house in Stockbridge
One block from Main St Stockbridge

One block from Main St Stockbridge

Stockbridge, MA
Situated in Stockbridge, this vacation home is within a 10-minute walk of Mission House and Berkshire Theatre Festival. Naumkeag and National Shrine of the Divine ...
One block from Main St Stockbridge
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Hancock, MA
Situated in Hancock, this condo building is 0.1 mi (0.1 km) from Jiminy Peak Mountain Resort and within 6 mi (10 km) of Mount Greylock State Reservation and ...
4.2/5Excellent! (1,417 reviews)
"Very nice location, nice views. Units were immaculate."

Reviewed on Sep 13, 2021

Vacation Village in the Berkshires
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd, Hancock, MA
The price is $139 per night from Oct 17 to Oct 17
Located in the mountains, this Hancock condo resort offering ski-in/ski-out access is 6.1 mi (9.7 km) from Mount Greylock State Reservation Visitor Center and ...
4/5Very Good! (729 reviews)
"Very small pool area, crowded."

Reviewed on Sep 20, 2021

Jiminy Peak Mountain Resort
The Ponds at Foxhollow by Capital Vacations

The Ponds at Foxhollow by Capital Vacations

3 out of 5
3 Foxhollow Drive Route 7, Lenox, MA
Situated in the entertainment district, this condo building is within 3 mi (5 km) of The Mount, Housatonic River, and Animagic Museum of Animation. Lee Library ...
4.2/5Very Good! (51 reviews)
"Peaceful surroundings, lovely view of the pond"

Reviewed on Sep 22, 2021

The Ponds at Foxhollow by Capital Vacations
Cabin in Becket

Cabin in Becket

Becket, MA
The price is $150 per night from Oct 1 to Oct 1
Located in Sherwood Forest, this vacation home is 3 mi (4.8 km) from Iroquis Waterfront and within 6 mi (10 km) of October Mountain State Forest and Jacob's ...
4.3/5Excellent! (9 reviews)
Just what we needed
"My husband and I - along with our two dogs - were looking for someplace restful to spend our anniversary. This really hit the spot. The cabin was simple and cozy, the kitchen had everything you need and the screen porch is divine. Even though it rained while we were there, we spent most of our time ..."

Reviewed on Sep 17, 2021

Cabin in Becket
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Becket, MA
Located in Sherwood Forest, this romantic cabin is within 6 mi (10 km) of Iroquis Waterfront, Jacob's Pillow, and October Mountain State Forest. Becket Land ...
4.6/5Wonderful! (86 reviews)
A Cozy, Scenic Spot
"My husband and I stayed at the house with our daughter (21 months old) and our small dog. We had a wonderful time! The kitchen was well supplied with pans, dishes, soap, etc., and posted all around the house were helpful instructions on how to use everything. We were able to fit a Pack 'N Play crib ..."

Reviewed on Aug 21, 2021

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
1BR Suite on Jiminy Peak Mountain with New Country Decor and perks. Ski on/off

1BR Suite on Jiminy Peak Mountain with New Country Decor and perks. Ski on/off

Hancock, MA
Offering ski-in/ski-out access, this aparthotel in Hancock is in the mountains, 0.1 mi (0.1 km) from Jiminy Peak Mountain Resort, and close to winter activities ...
5/5Exceptional! (1 review)
Ideal Retreat
"Great location for all Berkshire actitivites. Plenty of room, well furnished and stocked, and an attentive host"

Reviewed on Sep 8, 2021

1BR Suite on Jiminy Peak Mountain with New Country Decor and perks. Ski on/off
Star Gazer Farm

Star Gazer Farm

East Nassau, NY
Situated in East Nassau, this vacation home is 7.7 mi (12.3 km) from New Lebanon Library and 10.6 mi (17.1 km) from Pittsfield State Forest. Jiminy Peak Mountain ...
5/5Exceptional! (2 reviews)
Serene and beautiful space
"My husband and I wanted a weekend getaway that would allow us to swim. We didn't expect to find someplace so calming and interesting! The pool was fantastic - definitely got good use from it! There was a gold cart available to drive around the property which was a nice little perk. There's wildlife ..."

Reviewed on Aug 26, 2021

Star Gazer Farm
NEW Secluded A-Frame Cabin: Fire Pit, Walk to Lake

NEW Secluded A-Frame Cabin: Fire Pit, Walk to Lake

Becket, MA
Located in Sherwood Forest, this cabin is 2.8 mi (4.5 km) from Iroquis Waterfront and within 6 mi (10 km) of October Mountain State Forest and Jacob's Pillow. ...
4.7/5Exceptional! (3 reviews)
An Amazing Getaway
"We really enjoyed our stay at the A-Frame cabin. The place is just as great as it looks in the pictures. Such a cozy & comfortable place to stay! Communication with Kathy & Chris was top notch. They were excellent hosts. The cabin felt so secluded with the lake right across from it. We can't wait ..."

Reviewed on Mar 31, 2021

NEW Secluded A-Frame Cabin: Fire Pit, Walk to Lake
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns

Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns

Sandisfield, MA
Situated in Sandisfield, this cabin is within 9 mi (15 km) of Otis Ridge, Ashintully Gardens, and Beartown State Forest. Bidwell House Museum and County Beach ...
4.7/5Exceptional! (13 reviews)
loved it!
"a beautiful spot- clean, quiet, everything we needed for a wonderful weekend! We'll be back!"

Reviewed on Sep 7, 2021

Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
LOFT ON MAIN ST

LOFT ON MAIN ST

Great Barrington, MA
The price is $350 per night from Oct 1 to Oct 1
Situated in Great Barrington, this apartment building is within a 5-minute walk of Mahaiwe Performing Arts Center and Housatonic River. Lake Mansfield Park and ...
5/5Exceptional! (1 review)
A real vacation destination
"Every aspect of the loft is beautiful! The style makes for a comfy, cozy, serene, and visually stimulating destination. We loved our stay here because we felt like we got to stay in a very chic space so that we got a real vacation destination!"

Reviewed on Sep 27, 2021

LOFT ON MAIN ST
Spacious 3BR 3 BA on Jiminy Mountain Resort 1900 SqFt w Tons of Perks

Spacious 3BR 3 BA on Jiminy Mountain Resort 1900 SqFt w Tons of Perks

Hancock, MA
Located in the mountains, this Hancock condo building offering ski-in/ski-out access is 0.2 mi (0.3 km) from Jiminy Peak Mountain Resort and within 9 mi (15 ...
5/5Exceptional! (16 reviews)
Fantastic place and fantastic value!
"Wow! This three-level condo has it all AND pet friendly!! The condo is in great shape and very clean. First-floor bedroom and game room and bathroom - perfect place for the kids. Main floor spacious living area and kitchen and full bath and laundry, with a storage area on the front porch for gear. ..."

Reviewed on Aug 30, 2021

Spacious 3BR 3 BA on Jiminy Mountain Resort 1900 SqFt w Tons of Perks
Don't see what you're looking for?
See all available properties in Stockbridge
View all properties
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.

Large Group Cabins Stockbridge

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Becket, MA
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
East Otis Reservoir Cabin w/ Porch - Walk to Lake!

East Otis Reservoir Cabin w/ Porch - Walk to Lake!

Otis, MA
East Otis Reservoir Cabin w/ Porch - Walk to Lake!
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.

Everything you need to know about Stockbridge vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Stockbridge vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on … and on. 

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Stockbridge vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Stockbridge vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Stockbridge. If you’re looking for a little peace, consider booking during the quieter months, such as July, August, June. For more hustle and bustle, you may prefer to visit in July, August, June. 

Prices vary throughout the year. January is the cheapest month to visit, with July the most expensive. 

Your chosen location, property type, and amenities will impact the cost of your trip, too. Right now, Stockbridge vacation rentals range between $139 per night and $350 per night.

How to find incredible deals on Stockbridge rentals

At Expedia, we put the best Stockbridge vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Stockbridge rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Stockbridge vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Stockbridge. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions