Holiday Rentals in Stockbridge

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Stockbridge holiday rentals

A two-story house with a front porch, surrounded by a garden with various plants and rocks.

1. 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, (42 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveller
The price is €734
includes taxes & fees
23 Nov - 24 Nov
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Exterior

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,257 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is €96
includes taxes & fees
6 Dec - 7 Dec
Berkshire Mountain Lodge
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

3. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.8 out of 10, Excellent, (10 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is €96
includes taxes & fees
12 Nov - 13 Nov
Cozy 1-bedroom studio in serene Great Barrington with AC
Indoor pool

4. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,830 reviews)
"Great resort, great location very spacious."
United States
Marcos
The price is €90
includes taxes & fees
6 Dec - 7 Dec
Vacation Village in the Berkshires
A dining area with a wooden table, chairs, and a ceiling fan.

5. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is €269
includes taxes & fees
8 Nov - 9 Nov
Leaf-Peeper Paradise in the Berkshires
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

6. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is €554
includes taxes & fees
9 Nov - 10 Nov
Secluded Family Home in Serene Stockbridge Woods
A glass-fronted cabinet with multiple shelves, each holding folded towels.

7. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
United States
Eric H.
The price is €265
includes taxes & fees
8 Nov - 9 Nov
Sweet Cozy Victorian in Housatonic. Close to everything.
A residential garden with a stone border, various plants, and a house in the background.

8. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is €292
includes taxes & fees
9 Nov - 10 Nov
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A modern living room with a sofa, armchair, coffee table, and TV.

9. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
9.6 out of 10, Exceptional, (4 reviews)
"house was very clean, spacious and well equipped with everything we needed. Great communication with the host. Perfect location for our trip to Tanglewood."
United States
neil s.
Spacious Central Berkshires Home for Groups
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

10. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.8 out of 10, Excellent, (8 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is €179
includes taxes & fees
7 Nov - 8 Nov
NEW RENO - Chalet-style farm loft near Tanglewood
A living room with a sofa, armchairs, a coffee table, and a television.

11. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
10.0 out of 10, Exceptional, (12 reviews)
"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."
United States
Patricia O.
The price is €530
includes taxes & fees
8 Nov - 9 Nov
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

12. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is €289
includes taxes & fees
9 Nov - 10 Nov
Home in Great Barrington
A dining area with a wooden table and chairs, a view of greenery and mountains through large windows, and a balcony with a railing.

13. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!
Richmond
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay in the Berkshires! The house was lovely, very clean, and such a cozy place to spend a fall weekend. The overlook was absolutely stunning, especially with all the beautiful fall foliage! We loved that the property felt peaceful and tucked away while still being a short drive to Lenox, nearby towns, and plenty of great hiking trails. The host was so kind and always quick to respond, which made everything easy from start to finish. We really enjoyed our stay and would...
United States
Delaney M.
Ellie’s Overlook, best view in the Berkshires!
A modern living room with a sectional sofa, wooden beams, a large window, and a view of the outdoors.

14. Beautiful and Private Home Centrally Located in the Berkshires

Beautiful and Private Home Centrally Located in the Berkshires
West Stockbridge
The price is €1,163
includes taxes & fees
16 Nov - 17 Nov
Beautiful and Private Home Centrally Located in the Berkshires
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

15. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is €246
includes taxes & fees
9 Nov - 10 Nov
Real Estate: Therapy - Lake, Laundry, Love it
A spacious living room with a dining area, a kitchen, and a large window.

16. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is €194
includes taxes & fees
8 Nov - 9 Nov
1800s Carriage house in Berkshires / Hudson Valley
A modern kitchen with a dining area, built-in shelves, and a large window.

17. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Lenox
The price is €264
includes taxes & fees
7 Nov - 8 Nov
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

18. 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, (10 reviews)
"My wife and I had a lovely time staying here. Great location, only a couple of miles away from Jacobs Pillow. The lakes are clean and great for paddle boarding. Check in and out was a breeze, Nicole was a pleasure to work with. Thanks for a nice get away."
United States
Brian C.
The price is €322
includes taxes & fees
8 Nov - 9 Nov
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

19. 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, (10 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 €1,121
includes taxes & fees
8 Nov - 9 Nov
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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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Find out more about Stockbridge

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 €89 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 in Stockbridge close to Berkshire Botanical Garden, 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?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside Stockbridge is located near skiing, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Stockbridge?

Choose from 35 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 Berkshire Botanical Garden, or simply take in cultural attractions like Norman Rockwell Museum and Berkshire Theatre Festival. National Shrine of the Divine Mercy and Stockbridge Bowl 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.