The Berkshires Castles from CA $85

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Recommended hotels in The Berkshires

1. Garden Gables

Lenox

Eyee

CA $303 total

includes taxes & fees

Nov 18 - Nov 19

A hotel with a covered entrance, a registration desk, and a parking area.

2. The Yankee Inn

Lenox

Stephanie

CA $182 total

includes taxes & fees

Nov 20 - Nov 21

A multi-story hotel with a classic facade, large windows, and a prominent entrance.

3. Hotel On North

Pittsfield

Rosemarie

CA $184 total

includes taxes & fees

Nov 16 - Nov 17

A large, modern two-story house with a prominent gable roof, large windows, and a covered porch area.

4. Berkshires Untold

Lenox

Juan

CA $168 total

includes taxes & fees

Nov 17 - Nov 18

A lodge with a large building and a dock by a lake, surrounded by forest.

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

Lee

Tina

CA $169 total

includes taxes & fees

Dec 13 - Dec 14

A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

6. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Joseph

CA $143 total

includes taxes & fees

Dec 7 - Dec 8

A Super 8 motel with a two-story building, a parking lot, and a picnic table.

7. Quality Inn Lee - Lenox South

Lee

Bernardo Jr

CA $136 total

includes taxes & fees

Dec 6 - Dec 7

A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

8. Courtyard by Marriott Lenox Berkshires

Lenox

Vandhana

CA $181 total

includes taxes & fees

Dec 13 - Dec 14

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

9. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

CA $278 total

includes taxes & fees

Nov 16 - Nov 17

A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

10. Monument Mountain Motel

Great Barrington

Martha

CA $95 total

includes taxes & fees

Nov 16 - Nov 17

A large building with a prominent tower, surrounded by trees and a winding road.

11. Berkshire Mountain Lodge

Pittsfield

Susan J

CA $154 total

includes taxes & fees

Dec 6 - Dec 7

A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

12. Vacation Village in the Berkshires

Williamstown

Carol

CA $144 total

includes taxes & fees

Nov 16 - Nov 17

A multi-story building with a symmetrical facade, multiple balconies, and a central tower.

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

South Lee

Michael

CA $204 total

includes taxes & fees

Nov 16 - Nov 17

A hotel entrance with a covered driveway, a sign for Hampton Inn & Suites by Hilton, and a brick building with multiple windows.

14. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

CA $172 total

includes taxes & fees

Dec 15 - Dec 16

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

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

Great Barrington

Md

CA $256 total

includes taxes & fees

Nov 19 - Nov 20

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

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

Pittsfield

Ruth

CA $164 total

includes taxes & fees

Dec 13 - Dec 14

A Quality Inn sign, a brick building, and a parking lot with cars.

17. Quality Inn Great Barrington

Downtown Great Barrington

David

CA $121 total

includes taxes & fees

Dec 6 - Dec 7

A large house with a covered patio area featuring outdoor seating and a fire pit.

18. The Whitlock

Lenox

Beverly

CA $173 total

includes taxes & fees

Dec 1 - Dec 2

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

19. The Red Lion Inn

Stockbridge

Lisabeth

CA $322 total

includes taxes & fees

Nov 29 - Nov 30

A multi-story hotel with a prominent entrance, a parking lot, and a flagpole.

20. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

CA $191 total

includes taxes & fees

Nov 22 - Nov 23

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Learn more about The Berkshires

Tucked in western Massachusetts, this region blends culture and nature with world-class museums and lush hiking trails. Catch a summer concert at Tanglewood, explore Norman Rockwell's art in Stockbridge, or ski the slopes at Jiminy Peak in nearby Hancock.

See all hotels in The Berkshires

A large white building with multiple chimneys, surrounded by lush gardens with various flowers.

Top reviews in The Berkshires

A large, two-story house with a well-maintained lawn and a fence.

Devonfield Inn B&B

Lee

10/10 Excellent

We stayed at the Devonfield Inn in mid-October during peak foliage season. The hotel is a wonderful historic home built in 1800 with much of its historic character preserved. Our hosts were so welcoming and made us feel at home. The room was very comfortable and breakfast was fantastic. In the morning, we got a special surprise to see a bear on the patio drinking from the fountain and robbing the bird feeder. Overall we highly recommend the Devonfield. We will definitely go back.