Stockbridge Vacation Rentals

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Vacation Rentals in Stockbridge

Tranquil Retreat 6-BR Total in the Berkshires

Tranquil Retreat 6-BR Total in the Berkshires

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

10.0 out of 10, Exceptional, (5)
"My wife, two kids, and chocolate lab spent a few days at the cottage to enjoy the snow and hot tub. Everything was set up exactly as described and Nicole was very friendly and proactive. We had a great time and would do it again "
The price is CA $218
CA $534 total
includes taxes & fees
Jul 7 - Jul 8
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

The price is CA $227
CA $545 total
includes taxes & fees
Jul 22 - Jul 23
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.

10.0 out of 10, Exceptional, (2)
"This property was amazing! Very clean and spacious, perfect location for a nice peaceful getaway. Kendra was very communicative and made sure our stay was comfortable. 10/10 highly recommend you to stay here. "
The price is CA $388
CA $630 total
includes taxes & fees
Jul 16 - Jul 17
Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...
The price is CA $148
CA $196 total
includes taxes & fees
Aug 3 - Aug 4
Deluxe Queen Room with 2 Queen Beds

Spacious 5-bedroom house in charming Lee with WiFi

The price is CA $517
CA $1,007 total
includes taxes & fees
Jul 16 - Jul 17
Spacious 5-bedroom house in charming Lee with WiFi

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (252)
"One of the best properties i've ever stayed at "
The price is CA $272
CA $398 total
includes taxes & fees
Jul 31 - Aug 1
Berkshire Village Carriage House - Super Private!!

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (38)
"The property was centrally located for skiing, and was a comfortable stay."
The price is CA $322
CA $684 total
includes taxes & fees
Jul 30 - Jul 31
Cheerful 3-bedroom cottage with woodstove

Home in Great Barrington

9.8 out of 10, Exceptional, (21)
"Our family had a wonderful experience and stay. "
The price is CA $404
CA $597 total
includes taxes & fees
Jul 9 - Jul 10
Home in Great Barrington

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"Nice, cozy, clean house with character. Great location as we could walk to town. Would stay again for sure."
The price is CA $612
CA $998 total
includes taxes & fees
Jul 7 - Jul 8
Great Barrington Get Away

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

9.8 out of 10, Exceptional, (70)
"We had a wonderful stay, thank you! "
The price is CA $356
CA $741 total
includes taxes & fees
Jul 7 - Jul 8
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Comfortable Berkshires retreat on mtn resort, SISO

9.6 out of 10, Exceptional, (4)
"Hosts were very responsiveHouse was clean and well maintainedExcellent locationOverall great stay"
The price is CA $219
CA $658 total
includes taxes & fees
Jul 7 - Jul 8
Comfortable Berkshires retreat on mtn resort, SISO

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is CA $745
CA $1,408 total
includes taxes & fees
Jul 8 - Jul 9
Hancock Village Inn at Jiminy Peak

Near Tanglewood: Historic Summer Retreat

9.4 out of 10, Exceptional, (20)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is CA $233
CA $548 total
includes taxes & fees
Jul 9 - Jul 10
Near Tanglewood: Historic Summer Retreat

NEW RENO Historic Creamery in Berkshires w/hot tub

The price is CA $277
CA $650 total
includes taxes & fees
Jul 7 - Jul 8
NEW RENO Historic Creamery in Berkshires w/hot tub

Perfect House In Hillsdale, Brings Friends & Fam

8.6 out of 10, Excellent, (4)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
Perfect House In Hillsdale, Brings Friends & Fam

Dreamy 6 Bedroom House, Come Enjoy Hillsdale!

9.0 out of 10, Wonderful, (2)
"Our family of 12 really enjoyed staying in this 5-bedroom historic house! It had everything we needed and we loved the decor. "
Dreamy 6 Bedroom House, Come Enjoy Hillsdale!

Majestic views Hot tub Firepit Games Sleeps 14

The price is CA $1,277
CA $2,209 total
includes taxes & fees
Aug 4 - Aug 5
Majestic views Hot tub Firepit Games Sleeps 14

The Lakeshore House

The price is CA $660
CA $1,052 total
includes taxes & fees
Jul 7 - Jul 8
The Lakeshore House
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.
Save an average of 15% on thousands of hotels when you're signed in

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?

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT: This vacation home rental outside of Stockbridge is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease 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. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Stockbridge?

Choose from 29 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 Housatonic River 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.