Stockbridge Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Stockbridge vacation rentals

Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (39 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is ￥73,260
￥136,266 total
includes taxes & fees
May 31 - Jun 1
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Smart TV

Light-filled Carpenter's Cottage

Light-filled Carpenter's Cottage
Stockbridge
The price is ￥39,019
￥80,054 total
includes taxes & fees
May 31 - Jun 1
Light-filled Carpenter's Cottage
Private kitchen

Light Filled Modern Rustic 3-bedroom house in charming Stockbridge

Light Filled Modern Rustic 3-bedroom house in charming Stockbridge
Stockbridge
The price is ￥54,324
￥108,711 total
includes taxes & fees
May 31 - Jun 1
Light Filled Modern Rustic 3-bedroom house in charming Stockbridge
Terrace/patio

BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"The place exceeded expectations. Clean, cute space. Roomier than expected. Hot tub was on and at a good temperature. The Main Street with restaurants and bars is literally a 4 minute walk, yet the house feels secluded in a good way. Really enjoyed our stay."
United States
jack h.
The price is ￥39,815
￥50,114 total
includes taxes & fees
Jun 3 - Jun 4
BLUSH: Boutique TINY home*private spa*walk to town
Family Bungalow

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (10 reviews)
"Healthy food too!"
United States
GEORGINA
The price is ￥14,861
￥16,601 total
includes taxes & fees
Jun 8 - Jun 9
Huttopia Berkshires
Dining

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is ￥34,295
￥56,309 total
includes taxes & fees
Jun 1 - Jun 2
Sugar Shack - 300 square feet of pure sweetness.
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,375 reviews)
"Everything was great Room staff kitchen and pool . It was a quiet and peaceful stay"
United States
William
The price is ￥19,184
￥23,179 total
includes taxes & fees
May 31 - Jun 1
Vacation Village in the Berkshires
Property grounds

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is ￥30,865
￥73,496 total
includes taxes & fees
Jun 1 - Jun 2
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is ￥63,704
￥109,760 total
includes taxes & fees
Jun 2 - Jun 3
Guesthouse Cabin vacation rentals in Berkshire County
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥37,745
￥80,231 total
includes taxes & fees
Jun 2 - Jun 3
Cheerful 3-bedroom cottage with woodstove
TV, fireplace, printers

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (5 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is ￥90,157
￥211,534 total
includes taxes & fees
May 29 - May 30
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (31 reviews)
"Everything was as advertised!"
United States
Jessica S.
The price is ￥36,837
￥56,268 total
includes taxes & fees
Jun 2 - Jun 3
Home in Great Barrington
Outdoor spa tub

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is ￥25,513
￥61,052 total
includes taxes & fees
May 31 - Jun 1
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Great location and nice size house for a family of 5. We had a couple hiccups but the host responded quickly and handled things promptly. "
United States
Jennifer L.
The price is ￥32,250
￥50,433 total
includes taxes & fees
Jun 8 - Jun 9
Cozy Riverside Berkshires Retreat
House (3 Bedrooms) | Interior

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is ￥31,215
￥88,171 total
includes taxes & fees
May 29 - May 30
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Fridge, microwave, oven, stovetop

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is ￥75,649
￥137,157 total
includes taxes & fees
Jun 4 - Jun 5
Spacious 5-bedroom house in charming Lee with WiFi
TV, stereo, offices

Perfect Nature Haven In Great Barrington

Perfect Nature Haven In Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (8 reviews)
"Their place was one of the cleanest rental cabins we have ever been, the house is in a great location with beautiful surroundings, the check in and check out was extremely easy for a family with little kids, loved the place and we hope to be back!"
United States
Ethel B.
Perfect Nature Haven In Great Barrington
Outdoor dining

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is ￥42,857
￥78,647 total
includes taxes & fees
May 31 - Jun 1
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥23,220
￥59,558 total
includes taxes & fees
May 31 - Jun 1
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Exterior

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Very clean, fully stocked kitchen,great location "
United States
Karen H.
The price is ￥31,583
￥72,175 total
includes taxes & fees
Jun 1 - Jun 2
Near Tanglewood: Historic Summer Retreat
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 Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"We arrived after hours and had a pleasant check in experience with security. We had a presidental room that had two kings and a kitchen plus a large living room for the kids to play. The room was clean and the overall property was clean and in good condition. The room also had a nice patio that overlooked the train tracks and was relaxing. Overall, the room was quiet and it was a great spot to reset. We took advantage of the on-site activities and gameroom. The kids enjoyed the playground behind the game room. We would recommend and stay again!"
Janette 8-night trip
Posted 10 hours ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Find out more about Stockbridge

Search for holiday rentals in Stockbridge on Expedia! You can easily find your home rentals, villas, holiday apartments in Stockbridge using one of the methods below:

  • View our selection of featured holiday rentals in Stockbridge
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  • Enter your travel dates to view the best deals on holiday rentals in Stockbridge while they last

Look no further and take a look at our great range of rental properties in Stockbridge!

Frequently asked questions

Can I find a vacation rental in Stockbridge?

Yes, we offer vacation rentals in Stockbridge close to Berkshire Botanical Garden, or you can select a more secluded option if you want a relaxing stay. Our travelers say Stockbridge has a good selection of bars. Make sure you have time to check out the gardens and museums during your trip.

What are some of the best vacation rentals in Stockbridge?

Spacious Living, Covered Porch & Forest Setting | Beaver Creek by AvantStay: Visitors like this Stockbridge vacation home rental. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Stockbridge?

Choose from 34 Expedia vacation rentals in Stockbridge for a memorable vacation.

What’s there to see and do in Stockbridge?

Enjoy the outdoors at Naumkeag Museum and Berkshire Botanical Garden, or simply take in cultural attractions like Norman Rockwell Museum and Mission House. National Shrine of the Divine Mercy and Stockbridge Bowl are other places to visit while you're in town.

What’s a vacation rental in Stockbridge like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Stockbridge. Vacation rentals feature extras such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for family trips.