Hotels in Stockbridge

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Tonight
Oct 3 - Oct 4
Tomorrow
Oct 4 - Oct 5
Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

Where to stay in Stockbridge?

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A covered porch with wicker furniture and hanging flower baskets.

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
$161
$230 total
includes taxes & fees
Nov 3 - Nov 4
The Red Lion Inn
Front of property
A hallway with wooden bookshelves, a door, and a bedroom with a bed and floral wallpaper.
A living room with a fireplace, leather sofas, and a dog.
A stone fountain surrounded by trees in a park setting.

2. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
$365
$428 total
includes taxes & fees
Nov 1 - Nov 2
The Inn at Stockbridge
A two-story house with a brick entrance and a white facade.
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.
A neatly arranged bedroom with a bed, bedside table, and a dresser.
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.

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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Stockbridge
$382
$462 total
includes taxes & fees
Nov 1 - Nov 2
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lakeside lodge with a dock, fishing rods, and outdoor seating.
A dining area with large windows, wooden furniture, and a view of a lake.
A lodge with a large building and a dock by a lake, surrounded by forest.

4. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
$116
$129 total
includes taxes & fees
Nov 1 - Nov 2
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.
A hotel room with a bed, a desk, a television, a microwave, and a sofa.
A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

5. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
Lee
$110
$122 total
includes taxes & fees
Oct 25 - Oct 26
Quality Inn Lee - Lenox South
A large house with a balcony and a grassy yard.
A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.
A room with a white desk, two floral chairs, a small round table with a plant, a hanging lamp, and two framed artworks on the wall.
A two-story building with a gabled roof and a chimney.

6. The Little Lion

The Little Lion
Great Barrington
$115
$128 total
includes taxes & fees
Oct 18 - Oct 19
The Little Lion
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.

7. The Yankee Inn

The Yankee Inn
Lenox
$106
$118 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.
A motel with a parking lot and several cars parked.
A row of white plastic chairs on a covered outdoor area with a white building in the background.
A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

8. Monument Mountain Motel

Monument Mountain Motel
Great Barrington
$67
$74 total
includes taxes & fees
Nov 1 - Nov 2
Monument Mountain Motel
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
A covered outdoor area with stone pillars and a view of a road and green hills.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A modern restaurant with wooden flooring, bar area, and seating arrangements.

9. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
$126
$140 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Lenox Berkshires
A red building with a sign reading "Shaker Mill Inn."
A covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.
A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.
A cozy living room with a sofa, a small table, and a bookshelf. There is a window with curtains, and a painting on the wall.

10. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
$139
$152 total
includes taxes & fees
Nov 1 - Nov 2
Shaker Mill Inn
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

11. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
$144
$160 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A dining area with a glass table, red walls, and framed artwork.
A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.
A modern living room with a fireplace, comfortable seating, and a large window with curtains.

12. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
$156
$179 total
includes taxes & fees
Oct 27 - Oct 28
The Cornell Inn, Lenox & The Berkshires
A hotel room with a bed, a desk, and two wall-mounted lamps.
A hotel room with a bed, two bedside tables, a desk, two chairs, and a large window with a view of greenery.
A hotel reception desk with an orange counter, a computer, a beverage cooler, and framed awards on the wall.
A coffee station with a Nescafé dispenser, a coffee machine, and a toaster.

13. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
Lee
$65
$73 total
includes taxes & fees
Oct 25 - Oct 26
Econo Lodge Lee - Great Barrington
A large house with a covered patio area featuring outdoor seating and a fire pit.
A corner dining area with a wooden table set for four, surrounded by upholstered chairs.
A cozy lounge area with plush seating, a fireplace, and large windows offering a view of the outdoors.
A sunlit room with large windows, a stone floor, and two rocking chairs.

14. The Whitlock

The Whitlock
Lenox
$131
$146 total
includes taxes & fees
Nov 2 - Nov 3
The Whitlock
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.
A hotel room with a wooden desk, a television, a mirror, and a bathroom visible through an open door.
A hotel room with a bathroom, a bed, a desk, and a nightstand.
A hotel reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.

15. Quality Inn Great Barrington

Quality Inn Great Barrington
Great Barrington
$76
$85 total
includes taxes & fees
Nov 1 - Nov 2
Quality Inn Great Barrington
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.
A grocery store with shelves stocked with snacks and beverages, a refrigerated display case, and a wall with hexagonal patterns.
Pool

16. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
$116
$129 total
includes taxes & fees
Nov 3 - Nov 4
Hampton Inn & Suites Berkshires-Lenox
A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.
A living room with a patterned carpet, two sofas, a dining table, and chairs.
A motel with a two-story structure, multiple rooms with red doors, and a central staircase.
A hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.

17. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
Great Barrington
$79
$88 total
includes taxes & fees
Oct 18 - Oct 19
Travelodge by Wyndham Great Barrington Berkshires
A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.
A hotel room with two beds, a chair, and a bedside table with a phone.
A covered corridor with a metal railing, white walls, and a view of a street with parked cars.
A standard rectangular bathtub with a single faucet, tiled walls, and a geometric patterned floor.

18. Sunset Inn

Sunset Inn
Lee
$84
$94 total
includes taxes & fees
Oct 5 - Oct 6
Sunset Inn
A group of people performing yoga in an outdoor setting with grass and trees.
A motel with a row of rooms, a parking lot, and a hilly backdrop.
A hotel room with a flat-screen TV, a microwave, a refrigerator, a wooden dresser, a bedside lamp, and a framed picture on the wall.
A reception desk with a framed floral painting, a deer head, and a sign about pets.

19. Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
West Stockbridge
$77
$84 total
includes taxes & fees
Oct 4 - Oct 5
Pleasant Valley Motel West Stockbridge
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A garden with wooden Adirondack chairs and a stone pathway.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

20. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
$91
$124 total
includes taxes & fees
Nov 2 - Nov 3
Berkshire Mountain Lodge
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Our prices for hotels in Stockbridge are cheapest in May
Price trends for hotels in Stockbridge
Pricing is based on two traveler single night rates
View properties in October
Typical weather for Stockbridge
October
High 14°C / low 6°C. Sunny most days.
View properties in October
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7°
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-8°
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12°
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19°
8°
23°
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27°
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Monthly weather averages (˚C)

Top landmarks in Stockbridge

Norman Rockwell Museum

9.4/10 (347 reviews)
Norman Rockwell Museum is 0.8 mi (1.2 km) from central Stockbridge, why not stop by during your stay. If you want to experience more of the culture Stockbridge has to offer, head to Berkshire Botanical Garden, Naumkeag Museum, and National Shrine of the Divine Mercy.
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National Shrine of the Divine Mercy

9.0/10 (83 reviews)
If seeing the sights is on your list of things to do, head to National Shrine of the Divine Mercy— just one of the landmarks located 0.5 mi (0.8 km) from central Stockbridge.
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Naumkeag Museum

9.4/10 (10 reviews)
If museums are on your list of things to see, then you might want to head to Naumkeag Museum, located in the heart of Stockbridge.If you want to see more of the museums in Stockbridge, you can easily walk to Mission House.
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Berkshire Botanical Garden

9.4/10 (14 reviews)
Ready for an education in local botany? Berkshire Botanical Garden should make your list of places to visit, located 1.2 mi (2 km) from central Stockbridge. Want to stretch your legs some more? Head to Naumkeag Museum and The Mount, both nearby.
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Stockbridge Bowl

Check out the water views and take some great vacation pics at Stockbridge Bowl in Stockbridge.
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Frelinghuysen Morris House and Studio

8.2/10 (10 reviews)
Frelinghuysen Morris House and Studio is 4.4 mi (7 km) from central Stockbridge, why not stop by during your stay. If you want to experience more of the culture Stockbridge has to offer, head to Tanglewood Music Center, Shakespeare and Company, and Lenox Library.
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Berkshire Theatre Festival

8.8/10 (3 reviews)
Berkshire Theatre Festival is 0.9 mi (1.5 km) from central Stockbridge, why not stop by during your stay. If you enjoy the show and want to see another, Shakespeare and Company and Tanglewood Music Center are both not far.
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Schantz Galleries

7.2/10 (5 reviews)
Art fans might want to browse the collections at Schantz Galleries in Stockbridge. If you want to see more of the art galleries in Stockbridge, Norman Rockwell Museum and Art et Industrie aren't far.
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Learn more about Stockbridge

Wander through Norman Rockwell's America at his museum, where small-town life springs from canvas to memory. The red-brick Main Street looks suspiciously like his famous Christmas painting because, well, it is. Summer brings world-class music when Tanglewood hosts the Boston Symphony Orchestra in nearby Lenox. History buffs can explore the Mission House and Naumkeag's elegant gardens with their curious blue stairs. The Berkshire Botanical Garden offers seasonal splendor without the crowds of bigger attractions. For a perfect afternoon, grab a coffee on Main Street before heading to the Housatonic River, where locals fish in spots they'll reluctantly share if asked nicely.

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

Check out reviews of Stockbridge hotels guests love

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Great location and great amenities!!"
Phillip 1-night trip
Posted less than an hour ago
Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"I have stayed here multiple times. My unit this trip was very clean, well equipped and comfortable. The check in process and front desk staff were terrific. My only issue was a strong smell of marijuana coming through the slider and bedroom window . The staff gave me a fan to blow the smell back out however it was an issue throughout my stay."
Susan 7-night trip
Posted 14 hours ago
Berkshire Mountain Lodge
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"Was only there for one night. But great hotel, room, staff, and breakfast."
Terry 1-night trip
Posted 23 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Hotel On North

Hotel On North

10/10 Excellent
"Delightful place with charm and warmth and character. I would love to come back."
Richard 1-night trip
Posted 2 days ago
Hotel On North
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"Wonderful resort"
Ofer 2-night trip
Posted 4 days ago
Holiday Inn Club Vacations Oak 'n Spruce Resort

Frequently asked questions

What hotels do travelers like in Stockbridge?
Guests like The Red Lion Inn, The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood and Berkshire Mountain Lodge.
Can I book refundable hotels in Stockbridge?
If you want the flexibility to change your plans to Stockbridge, most accommodations offer refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
Where can I stay in Stockbridge if I want a vacation home instead of a hotel?
If you want to find a good alternative to a hotel, review our selection of 35 vacation homes. You can also consider one of the 5 apartments or 9 cottages.
What will the weather in Stockbridge be like during my vacation?
The warmest months in Stockbridge are usually July and August with an average temp of 66°F. January and February are the chilliest months when the average temp is 27°F. The rainiest months are October and July.
Why should I book my Stockbridge hotel with Hotels.com?
There are plenty of reasons to book your Stockbridge travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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