The Berkshires Hotel Guide - Romantic Hotels in The Berkshires, Massachusetts
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Top The Berkshires Romantic Hotels
Our top choices for The Berkshires romantic hotels

Shaker Mill Inn
Shaker Mill Inn
9.6 out of 10, Exceptional, (421)
The price is €178
includes taxes & fees
4 Sept - 5 Sept

Vacation Village in the Berkshires
Vacation Village in the Berkshires
8.6 out of 10, Excellent, (1961)
The price is €111
includes taxes & fees
7 Sept - 8 Sept

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
8.0 out of 10, Very good, (863)
The price is €104
includes taxes & fees
3 Sept - 4 Sept

The Dewey
The Dewey
8.8 out of 10, Excellent, (321)
The price is €165
includes taxes & fees
15 Sept - 16 Sept

Chestnut Lodge
Chestnut Lodge
2.0 out of 10, (2)

Kemble Inn
Kemble Inn
8.8 out of 10, Excellent, (31)

Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
10.0 out of 10, Exceptional, (96)

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
9.2 out of 10, Wonderful, (105)
The price is €321
includes taxes & fees
3 Sept - 4 Sept
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.
Top The Berkshires Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG
10/10 Excellent
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Hotel Theme
- Adventure Sport Hotels in The Berkshires
- Beach Hotels in The Berkshires
- Boutique Hotels in The Berkshires
- Business Hotels in The Berkshires
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- Golf Hotels in The Berkshires
- Green / Sustainable Hotels in The Berkshires
- Historic Hotels in The Berkshires
- Hotels with Air Conditioning in The Berkshires
- Hotels with Bar in The Berkshires
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- Hotels with Childcare in The Berkshires
- Hotels with Connecting Rooms in The Berkshires
- Hotels with Parking in The Berkshires
- Hotels with Pool in The Berkshires
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- Hotels with Yoga in The Berkshires
- Luxury Hotels in The Berkshires
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- Ski Hotels in The Berkshires
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More top The Berkshires Hotels
- Holiday Inn & Suites Pittsfield-Berkshires by IHG
- The Constance by the Lenox Collection
- Best Western Plus Berkshire Hills Inn & Suites
- Hotel On North
- Jiminy Peak Mountain Resort
- Holiday Inn Express & Suites Pittsfield - Berkshires
- Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
- Courtyard by Marriott Lenox Berkshires
- Monument Mountain Motel
- Cozy Corner Motel
- The Cornell Inn, Lenox & The Berkshires
- The Porches Inn at Mass MoCA
- The Villager Motel
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