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Check availability on Stockbridge Luxury Hotels

Our top choices for Stockbridge luxury hotels

Suite, Private Bathroom (RedBird Suite) | View from room

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
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (111 reviews)
  • cleanliness
    Escape to a mountain luxury bed & breakfast where refined elegance meets nature's beauty, just steps from the Norman Rockwell Museum.
"The Stockbridge Country Inn is the quintessential New England B&B! The owner, Diane, is the perfect host - very friendly and knowledgeable about the area. We stayed in The Maid's Suite which was extremely comfortable and beautifully decorated. Breakfast was always a delicious treat! The convenient location made access to sightseeing so easy."
United States
Linda
The price is AED 1,137
AED 1,375 total
includes taxes & fees
31 May - 1 Jun
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property - evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (138 reviews)
"Very enjoyable comfortable stay"
United States
Christopher
The price is AED 988
AED 1,104 total
includes taxes & fees
18 May - 19 May
Devonfield Inn B&B
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"We we were in the Out of Africa room, set apart in a complex of 4 suites in a unit apart from the Inn itself. The room was uniquely created to feel like an escape to Africa, and heated by a lovely gas fireplace. The breakfast both mornings, delicious. A perfect getaway!"
United States
Janis
The price is AED 965
AED 1,132 total
includes taxes & fees
21 May - 22 May
The Inn at Stockbridge
Exterior

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (365 reviews)
  • cleanliness
    Boutique Berkshire guesthouse features spacious suites, designer interiors, and easy access to cultural sites.
"We very much enjoyed the comfortable, large king bed and the cushy living room sofa."
United States
Angela
The price is AED 419
AED 468 total
includes taxes & fees
1 Jun - 2 Jun
The Central Downtown Inn & Suites
Thayer House, Room 205, 1 King bed | Premium bedding, individually decorated, individually furnished

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (91 reviews)
"this was a fabulous, relaxing stay in the countryside"
United States
Mary
The price is AED 1,212
AED 1,463 total
includes taxes & fees
18 May - 19 May
The Old Inn On The Green
Exterior detail

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (44 reviews)
"Hot tub in the cottage was wonderful."
United States
Dee
The price is AED 1,006
AED 1,124 total
includes taxes & fees
25 May - 26 May
Hampton Terrace Inn
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"We appreciate the larger room and renovate bathroom."
United States
Sirimon
The price is AED 2,314
AED 2,584 total
includes taxes & fees
25 May - 26 May
33 Main
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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Top Stockbridge Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"The room was nice, didn’t care for the smell in the room but I guess it’s normal. Room was clean. Nice area. Very cute town. Would definitely stay again. Loved the Bible in the drawer."
Tanya 1-night trip
Posted 7 hours ago
Quality Inn Great Barrington

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Frequently asked questions

Are you looking for a luxury hotel for your stay in Stockbridge?
During your visit, you might want to enjoy the bars which Stockbridge is known for.
What's the best high-end hotel in Stockbridge?
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood is a luxury B&B with a seasonal outdoor pool and a terrace, and it's a popular choice for Expedia travelers looking for an elegant place to stay.
When can I expect good weather in Stockbridge?
Planning for the weather is a good way to make your trip to Stockbridge relaxing and enjoyable, especially when you're splurging. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's there to see and do in Stockbridge?
Experience all that Stockbridge has to offer when you visit Naumkeag Museum, National Shrine of the Divine Mercy, and Norman Rockwell Museum. If you have extra time while you're in the area, you might want to see Berkshire Botanical Garden and Stockbridge Bowl.