Luxury Hotels in Stockbridge, Massachusetts

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Check availability on Stockbridge Luxury Hotels

Tonight
Feb 6 - Feb 7
Tomorrow
Feb 7 - Feb 8
This weekend
Feb 6 - Feb 8
Next weekend
Feb 13 - Feb 15

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, (110 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 P18,169
P21,980 total
includes taxes & fees
Feb 20 - Feb 21
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
The price is P24,072
P26,888 total
includes taxes & fees
Feb 23 - Feb 24
33 Main
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (291 reviews)
The price is P8,454
P9,916 total
includes taxes & fees
Feb 7 - Feb 8
Lakehouse Inn
Breakfast, lunch, dinner served; American cuisine

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90 reviews)
The price is P17,907
P21,609 total
includes taxes & fees
Feb 8 - Feb 9
The Old Inn On The Green
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
The price is P14,083
P16,517 total
includes taxes & fees
Feb 22 - Feb 23
The Inn at Stockbridge
Exterior detail

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (43 reviews)
The price is P12,909
P14,419 total
includes taxes & fees
Feb 8 - Feb 9
Hampton Terrace Inn
Living room

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (135 reviews)
Devonfield Inn B&B
50-inch flat-screen TV with cable channels, TV, streaming services

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (355 reviews)
  • cleanliness
    Boutique Berkshire guesthouse features spacious suites, designer interiors, and easy access to cultural sites.
The price is P5,930
P6,624 total
includes taxes & fees
Mar 8 - Mar 9
The Central Downtown Inn & Suites
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.
View all properties

Top Stockbridge Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"The staff is very helpful, and always willing to assist with any inquiries. The room was definitely clean and well-stocked throughout our entire stay."
Robin 1-night trip
Posted 1 day ago
The Yankee, Trademark Collection by Wyndham

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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