A stone staircase leading up to a blue arched entrance, surrounded by lush greenery and birch trees.

Stockbridge Vacation Rentals

Dates

November 2026

December 2026

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We are not like the others - we include taxes and fees

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Our top choices for Stockbridge vacation 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!

Stockbridge

Anonymous traveler

$718 nightly

Dec 1 - Dec 2

Total with taxes and fees

2. Berkshire Mountain Lodge

Pittsfield

Susan J

$106 nightly

Dec 10 - Dec 11

Total with taxes and fees

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Great Barrington

bob i.

$102 nightly

Nov 16 - Nov 17

Total with taxes and fees

4. Vacation Village in the Berkshires

Williamstown

Carol

$122 nightly

Dec 10 - Dec 11

Total with taxes and fees

A sandy beach with a lake and forest in the background.

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

Great Barrington

Kristin O.

$283 nightly

Nov 10 - Nov 11

Total with taxes and fees

A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

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

Housatonic

Eric H.

$257 nightly

Nov 10 - Nov 11

Total with taxes and fees

A dining area with a wooden table, chairs, and a ceiling fan.

7. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

$262 nightly

Nov 10 - Nov 11

Total with taxes and fees

A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

8. Secluded Family Home in Serene Stockbridge Woods

Stockbridge

Ofer C.

$534 nightly

Nov 10 - Nov 11

Total with taxes and fees

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

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

New Lebanon

Joanna P.

$190 nightly

Nov 10 - Nov 11

Total with taxes and fees

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

10. Home in Great Barrington

Great Barrington

Janet G.

$281 nightly

Nov 10 - Nov 11

Total with taxes and fees

A spacious living room with a dining area, a kitchen, and a large window.

11. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

$204 nightly

Nov 10 - Nov 11

Total with taxes and fees

A living room with a sofa, armchairs, a coffee table, and a television.

12. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

$526 nightly

Nov 10 - Nov 11

Total with taxes and fees

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Sherwood Forest

William C B.

$250 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

West Stockbridge

$1,149 nightly

Nov 16 - Nov 17

Total with taxes and fees

A modern kitchen with a dining area, built-in shelves, and a large window.

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

Lenox

$264 nightly

Nov 11 - Nov 12

Total with taxes and fees

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.

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

Sherwood Forest

Brian C.

$311 nightly

Nov 10 - Nov 11

Total with taxes and fees

A hot tub with a string of lights above it, set against a dark night sky.

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

Sherwood Forest

Frank M.

$326 nightly

Nov 10 - Nov 11

Total with taxes and fees

A cozy living room with a large window, wooden walls, and a television.

18. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Hancock

Maura D.

$185 nightly

Nov 10 - Nov 11

Total with taxes and fees

A bedroom with a wooden bed frame, a large window, and a painting of mountains on the wall.

19. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Hancock

patricia f.

$185 nightly

Nov 10 - Nov 11

Total with taxes and fees

A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

20. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington

Mary R.

$581 nightly

Nov 16 - Nov 17

Total with taxes and fees

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Find vacation rentals that suit your style

Top Stockbridge Hotel Reviews

The Inn at Stockbridge

Stockbridge

10/10 Excellent

Kevin

A two-story house with a brick entrance and a white facade.

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Stockbridge

10/10 Excellent

Charles

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

The Red Lion Inn

Stockbridge

10/10 Excellent

Michael

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

Devonfield Inn B&B

Lee

10/10 Excellent

Anonymous traveler

Shaker Mill Inn

West Stockbridge

10/10 Excellent

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...

Joe

A two-story building with a sign reading "Chambéry Inn".

Chambery Inn

Lee

10/10 Excellent

Elaine

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

Brook Farm Inn

Lenox

10/10 Excellent

roberta

A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

Inn at Silver Maple Farm

East Chatham

10/10 Excellent

Michelle

Wilder House Berkshires

Sheffield

10/10 Excellent

Liliana

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

10/10 Excellent

We were greeted by extremely friendly staff. Check in and check out was seamless. Room was very nice and immaculate. We especially liked the bathroom design - didn't have to trip over the toilet to get in the shower as in most hotels! Free breakfast was the usual fare, but in a very pleasant and uncrowded room. Appreciated the free US News and NY Times Beautiful indoor pool - wish we'd brought our bathing suits!

Anonymous traveler

A snow-covered outdoor area with a patio, seating, and a covered dining area.

The Cornell Inn, Lenox & The Berkshires

Lenox

10/10 Excellent

Lawrence

A building entrance with a large planter with purple flowers and a small tree.

Hotel On North

Pittsfield

10/10 Excellent

The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...

Steve

A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

Little Cat Lodge

Copake Falls

10/10 Excellent

Elisabeth

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

10/10 Excellent

Sheila

A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

South Lee

10/10 Excellent

I love this place and have stayed here before. Even with the precautions for COVID-19, my kids and I still had a great time. The check-in was smooth and safe. The room was clean and sanitized. In fact, we had to "break the seal" on the door to enter and the seal was evidence of the cleaning that was done. Of course, the arcade and movie theatre were closed, but that was no surprise. The pools were open and reservations required to ensure everyone could be safe and still have fun. Lots of...

David

Find out more about Stockbridge

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 low season months. For more hustle and bustle, you may prefer to visit Stockbridge in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $118 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

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

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?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental outside Stockbridge is located near skiing 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 35 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 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 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.

Stockbridge Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Stockbridge vacation rentals

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

2. Berkshire Mountain Lodge

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

4. Vacation Village in the Berkshires

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

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

7. Leaf-Peeper Paradise in the Berkshires

8. Secluded Family Home in Serene Stockbridge Woods

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

10. Home in Great Barrington

11. 1800s Carriage house in Berkshires / Hudson Valley

12. Sun Filled Lenox Retreat - Minutes to Tanglewood!

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

14. Beautiful and Private Home Centrally Located in the Berkshires

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

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

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

18. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

19. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

20. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Find vacation rentals that suit your style

Top Stockbridge Hotel Reviews

The Inn at Stockbridge

10/10 Excellent

Find out more about Stockbridge

Everything you need to know about Stockbridge vacation rentals

Stockbridge vacation rentals: An excellent choice for every season

How to find incredible deals on Stockbridge rentals

Frequently Asked Questions

Can I find a vacation rental in Stockbridge?

What are some of the best vacation rentals in Stockbridge?

How many vacation rentals will I find in Stockbridge?

What’s there to see and do in Stockbridge?

What’s a vacation rental in Stockbridge like?

Explore a world of travel with Expedia