Find Romantic Hotels in The Berkshires, MA

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Check availability on The Berkshires Romantic Hotels

Tonight
Sep 7 - Sep 8
Tomorrow
Sep 8 - Sep 9
Next weekend
Sep 12 - Sep 14
In two weeks
Sep 19 - Sep 21

Top The Berkshires Romantic Hotels

Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (425)
"Very casual and easy check in and out; lovely and substantial breakfast"
The price is ￥22,652
￥24,849 total
includes taxes & fees
Sep 10 - Sep 11
Shaker Mill Inn
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1993)
"Beautiful location!"
The price is ￥12,807
￥15,922 total
includes taxes & fees
Sep 21 - Sep 22
Vacation Village in the Berkshires
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (870)
"Consistently a clean room with welcoming staff."
The price is ￥16,070
￥17,950 total
includes taxes & fees
Sep 10 - Sep 11
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Dewey
Exterior

The Dewey

3.5 star property
8.6 out of 10, Excellent, (323)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is ￥27,127
￥30,301 total
includes taxes & fees
Sep 15 - Sep 16
The Dewey
Chestnut Lodge
Property grounds

Chestnut Lodge

3.5 star property
2.0 out of 10, (2)
"An absolutely horrible experience! My family (2 adults and my 6 year old son) had reserved this so-called hotel for $284 in June for a 13th Aug stay. After a full day at the Berkshires, we checked-in at 6 pm. This place is in a terrible location (unpaved roads, still-in construction steps). To our horror we found that the room had No Air-Conditioning. It was 90 degrees outside and all they had in the room was a ceiling fan. There were bugs in the room due to the heat. On top of it all the...
Chestnut Lodge
Kemble Inn
Exterior

Kemble Inn

3.5 star property
8.8 out of 10, Excellent, (31)
"Memorable. A wonderful hotel I every aspect. Faultless service from Scoyt and the team"
Kemble Inn
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Fridge, microwave, oven, stovetop

Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

10.0 out of 10, Exceptional, (97)
"amazing home, great communication with the host. "
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business center

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is ￥45,625
￥55,194 total
includes taxes & fees
Sep 22 - Sep 23
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (128)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
The Ponds at Foxhollow
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1002)
"Wonderful old inn; chock full of charm."
The price is ￥24,418
￥33,863 total
includes taxes & fees
Sep 10 - Sep 11
The Red Lion Inn
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Very enjoyable stay in a beautiful location! Clean, comfy, and nicely decorated condo! The staff is so helpful, and absolutely amazing. Couldn’t have had a better place to stay!"
Sandra 6-night trip
Posted 5 days ago
Vacation Village in the Berkshires
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

10/10 Excellent
"Fantastic breakfast, perfect location, fun vibe, beautiful pool area, an environment that encourages conversation with other guests. Room was spacious but needed a nightstand on either side of the bed. "
Leigh 1-night trip
Posted 2 weeks ago
The Porches Inn at Mass MoCA

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