A nighttime view of a residential area with houses adorned with holiday lights.

Luxury Hotels in Stockbridge, Massachusetts

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Check availability on Stockbridge Luxury Hotels

Next weekend
Jul 31 - Aug 2
In two weeks
Aug 7 - Aug 9

Our top choices for Stockbridge luxury hotels

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, (113 reviews)
  • cleanliness
    Escape to a mountain luxury bed & breakfast where refined elegance meets nature's beauty, just steps from the Norman Rockwell Museum.
The price is P20,420
P24,702 total
includes taxes & fees
Aug 9 - Aug 10
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (99 reviews)
The price is P22,933
P26,897 total
includes taxes & fees
Jul 27 - Jul 28
The Inn at Stockbridge
Front of property - evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (139 reviews)
The price is P25,295
P28,254 total
includes taxes & fees
Aug 25 - Aug 26
Devonfield Inn B&B
Exterior

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (379 reviews)
  • cleanliness
    Boutique Berkshire guesthouse features spacious suites, designer interiors, and easy access to cultural sites.
The price is P6,618
P7,392 total
includes taxes & fees
Jul 27 - Jul 28
The Central Downtown Inn & Suites
Exterior detail

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (44 reviews)
The price is P17,280
P19,302 total
includes taxes & fees
Aug 25 - Aug 26
Hampton Terrace Inn
Breakfast, lunch, dinner and brunch served

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)
The price is P20,409
P24,628 total
includes taxes & fees
Jul 28 - Jul 29
The Old Inn On The Green
Premium bedding, iron/ironing board, WiFi (free), individually decorated

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
The price is P46,268
P51,682 total
includes taxes & fees
Aug 16 - Aug 17
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Pool"
Tatsiana 4-night trip
Posted 2 hours ago
Vacation Village in the Berkshires

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.

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