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Find properties with these dates

Tonight
May 1 - May 2
Tomorrow
May 2 - May 3
This weekend
May 3 - May 5
Next weekend
May 10 - May 12

Top Holiday Rentals in Stockbridge

Fridge, microwave, oven, stovetop
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (10)
"The hosts have made this ranch house into an artsy, cozy place for families to rest and relax! Plenty of space for family hang outs and game playing, but also enough rooms for tweens or teens to get away and have alone time. Beautiful spaces throughout. We would have loved to enjoy the backyard space and screened-in porch if it hadn't been winter, but appreciated watching the snow falling while sipping coffee by the kitchen window! Close to Catamount ski area and minutes from Stockbridge shops...
Stockbridge Home, Come Experience The Berkshires!
Exterior
Find your Sanctuary at The Rectory at Stockbridge
10.0 out of 10, Exceptional, (1)
"We had 3 generations of family staying here after the holidays and the home provided everything we needed - wonderful location right in town, comfortable rooms, and large living spaces to play games and catch up. The kids, parents and grandparents all had a great time!"
The price is £815
per night
3 May - 4 May
Find your Sanctuary at The Rectory at Stockbridge
7 bedrooms, iron/ironing board, cots/infant beds, travel cot
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (28)
"We've stayed in a lot of home rentals - and across the board - this was the best place ever. The home was clean, nicely decorated and super comfortable. The hosts were easy to get a hold of and incredibly welcoming, leaving us with a generous basket of local treats. We loved the peaceful outdoor space and roamed all 40 acres. The pond was beautiful and if it had only been warmer we'd have jumped in the rowboat. We will be back for sure. A++ Thank you, Anna!"
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
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Fridge, microwave, oven, stovetop
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (7)
"My wife and young daughters live in central CT, and the drive to Becket was both scenic and relatively short at around an hour and a half. The property offers great privacy in a remote wooded setting in the heart of the always beautiful Berkshires. We brought our dog along, and we all were able to relax by the fire, read our favorite books, as well as peruse interesting titles on the impressive bookshelf built into the living room wall—a book lover’s delight. We admired the openness and light...
Pristine Home In Becket Woods
Property grounds
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (4)
"Perfect place to relax and have dogs as part of a mini vacation. Very clean, organized, and provided helpful local information. Will definitely stay there again."
Serene Acreage - Pond - Hiking Trails Nearby
Lake
Berkshire Lake access
10.0 out of 10, Exceptional, (41)
"Living space is bigger than the pictures, plenty of room for everyone, well stocked kitchen, everything we needed!"
Berkshire Lake access
Exterior
Quintessential 6-BR Berkshires Lodge
10.0 out of 10, Exceptional, (4)
"The house was perfect and Sydney was a great host. "
Quintessential 6-BR Berkshires Lodge
Property grounds
Private Island - On Largest Fresh Water Reservoir in Mass. 24' Pontoon boat
10.0 out of 10, Exceptional, (3)
"So grateful to Bill for such a wonderful stay! The cottage was so lovely and had everything you could need for a weekend on the lake. Will definitely be returning in the future 😊"
Private Island - On Largest Fresh Water Reservoir in Mass. 24' Pontoon boat
Fridge, microwave, oven, stovetop
Romantic and Secluded Berkshire's Gem
10.0 out of 10, Exceptional, (9)
"My friends and I had an amazing time staying in the cozy cabin. 9 of us slept comfortably, the place was spotless, and so cute. We hope to visit again."
Romantic and Secluded Berkshire's Gem
Exterior
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (15)
"We were a big group..16 adults and 7 children. The families with children were well situated with nearby or adjacent rooms. Everyone had comfortable rooms which afforded privacy and quiet times. Each room had its own beautiful newly renovated bathrooms ( with great water pressure). The living and dining rooms were large and comfortable. The dining table was a loooong table with benches all around which easily sat our crowd. The backyard was gorgeous with beautiful views of the distant mountains....
The Kemble- Built by a US Secretary of State in Lenox
Exterior
The Winthrop Estate - 12K SF 32 Acres
10.0 out of 10, Exceptional, (2)
"Absolutely stunning property - truly incredible stay. Recommend to anyone looking for a large group getaway. Fast WiFi, commercial grade kitchen and plentiful supplies make it easy for large groups. beautiful property and room for activities on a huge lawn. Highly recommend."
The Winthrop Estate - 12K SF 32 Acres
Interior
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (202)
"The property was quiet and clean."
Berkshire Village Carriage House - Super Private!!
Interior
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, (6)
"My wife and I were looking for a nice little getaway within reasonable driving distance and came across this great property. As soon as we saw the big windows in the living room we were sold. Definitely getting added to our short list of places to go back to."
Berkshires Cabin 2 Mi to Appalachian Trail!
Exterior
Moose Lodge by AvantStay | Luxe Berkshires Escape
9.8 out of 10, Exceptional, (10)
"It was unique, with unusual amenities, like the home theater and fabulous game room. Our weather was wintery, so this was such a comfortable and fun way for the family to spend time together!"
Moose Lodge by AvantStay | Luxe Berkshires Escape
Property grounds
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, (20)
"Relaxing get away. Great hot tub, table shuffleboard. 3 floors of comfort."
The Meadows House @ Otis Ridge w/ 7-person hot tub
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (181)
"Thank you, Justin, for sharing your beautiful home with my family. We had a very nice time and relaxed in the beautiful quiet surroundings. I was so excited when I saw some Norwex items as I am a consultant and also use Norwex in my home. We hope to visit again in the warmer months as it was a perfect memory for our family. Thanks again, The Short family"
Peace and quiet on the lake
Exterior
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (194)
"The house is beautifully remodeled and clean. Nice open area with all like new kitchen appliances. My friend and I are thinking of going back in the summer to enjoy the lake"
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Fridge, microwave, oven, stovetop
Beautiful, Private Estate w/ Pool, Pond, Rec Room, Gym, Library, Barn, Trails!
9.6 out of 10, Exceptional, (79)
"We had 4 families and grandparents all stay together for an unforgettable weekend at Bellavista. The house had enough space for us to hang out together playing charades in the great room, ping pong tournaments in the finished attic playroom, and making holiday ornaments at the large dining room table. There were also spaces to have quiet moments when you needed it...and we even enjoyed a beautiful hike at a nearby conservation area that Laurie recommended. The house was extremely clean, fully...
Beautiful, Private Estate w/ Pool, Pond, Rec Room, Gym, Library, Barn, Trails!
Property grounds
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, (49)
"This was our first stop on a long journey from VA to ME, traveling with 2 dogs. It was perfect, the dogs were safe with lots of freedom to roam. What a beautiful, peaceful village and sweet little cottage."
The price is £218
per night
2 May - 3 May
Perfect Vacation Get Away - Historical New Marlborough
Don't see what you're looking for?
See all available properties in Stockbridge
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.

Stockbridge Holiday Rental Travel Info

Number of holiday rentals
19
Popular accommodation
Stockbridge private holiday homes
Known landmarks
Ski Butternut, Norman Rockwell Museum and Bousquet Ski Area
International airports
Hartford, CT (BDL-Bradley Intl.), Pittsfield, MA (PSF-Pittsfield Municipal) and Albany, NY (ALB-Albany Intl.)

Other types of properties in Stockbridge you may be interested in

Fridge, microwave, oven, stovetop
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (10)
"The hosts have made this ranch house into an artsy, cozy place for families to rest and relax! Plenty of space for family hang outs and game playing, but also enough rooms for tweens or teens to get away and have alone time. Beautiful spaces throughout. We would have loved to enjoy the backyard space and screened-in porch if it hadn't been winter, but appreciated watching the snow falling while sipping coffee by the kitchen window! Close to Catamount ski area and minutes from Stockbridge shops...
Stockbridge Home, Come Experience The Berkshires!
Lobby
Life House Berkshires
3.5 star property
9.2 out of 10, Wonderful, (231)
"Very accommodating and friendly staff. Coffee in the morning was excellent. "
The price is £89
per night
5 May - 6 May
Life House Berkshires
Outdoor pool, pool loungers
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (870)
"What a pleasure to have the opportunity to stay in an historic inn such as the Red Lion. "
The price is £124
per night
6 May - 7 May
The Red Lion Inn
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Stockbridge holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Stockbridge holiday 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  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Stockbridge holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Stockbridge holiday rentals we have selected for you start as low as £815 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Stockbridge rentals

At Expedia, we put the best Stockbridge holiday 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 holiday.

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

Can I find a holiday rental in Stockbridge?

Yes, there are holiday rentals close to the most popular sights in Stockbridge, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 holiday rentals that Stockbridge has to offer?

Berkshire Village Carriage House - Super Private!!: This holiday home rental outside of Stockbridge is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in Stockbridge?

Choose from 33 Expedia holiday rentals in Stockbridge for a memorable holiday.

What’s there to see and do in Stockbridge?

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

What’s a holiday rental in Stockbridge like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Stockbridge. Holiday rentals offer extras like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for a small group gathering.

Recent reviews of Stockbridge properties
Expedia verified reviews

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

5/5 Excellent
"Just a nice, cozy and very clean little hotel. We would stay there again if in the area."
A verified traveller from Marion stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection
Posted 17 hours ago
The Black Swan Lee - Lenox, Ascend Hotel Collection