Find Hotels & Resorts for Couples in The Berkshires, MA

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Top The Berkshires Hotels & Resorts for Couples

Beautifully Renovated Colonial Home
5/5 Exceptional! (10 reviews)
Wonderful location
"Comfy, spacious house with a lots of character. Very central location for many Berkshire towns. Lovely grounds. Enjoyed our time there very much,"

Reviewed on Sep 4, 2021

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Beautifully Renovated Colonial Home
Federal House Inn
3.5 out of 5
1560 Pleasant Street, Route 102, South Lee, MA
4.8/5 Exceptional! (178 reviews)
"Beautiful old house. Personable, helpful and accommodating staff. Wonderful homemade breakfast, wine hour and snacks. We had a great stay."

Reviewed on Dec 8, 2019

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Federal House Inn
Courtyard by Marriott Lenox Berkshires
3 out of 5
70 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is $118 per night from Nov 1 to Nov 1
4.6/5 Wonderful! (333 reviews)
"Convenient location to downtown Lenox and surrounding towns we visited on our trip. Would have been nice if there was a restaurant inside the hotel. Breakfast options limited to Starbucks for a limited time in the morning. We did enjoy the pool and hot tub and the outdoor patio area was ..."

Reviewed on Oct 9, 2021

Courtyard by Marriott Lenox Berkshires
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The Cornell Inn, Lenox
3 out of 5
203 Main St, Lenox, MA
The price is $201 per night from Nov 8 to Nov 8
4.6/5 Wonderful! (311 reviews)
"My wife and I just spent three wonderful days at the Cornell Inn. The decor is beautiful and unique. The breakfasts were delicious and creative. The staff was friendly, helpful and attentive. And the location is very convenient."

Reviewed on Oct 19, 2021

The Cornell Inn, Lenox
Club Wyndham Bentley Brook
3 out of 5
1 Corey Road, Hancock, MA
4.6/5 Wonderful! (270 reviews)
"Everything one needs is at your disposal. It was peaceful, wonderful surroundings, great staff we couldn't have asked for a better place to stay! We can't wait to go back!!"

Reviewed on Oct 2, 2021

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Club Wyndham Bentley Brook
Birchwood Inn
3.5 out of 5
7 Hubbard Street, Lenox, MA
The price is $170 per night from Oct 27 to Oct 27
4.6/5 Wonderful! (78 reviews)
"Wonderful atmosphere and property history…close to other venues."

Reviewed on Oct 4, 2021

Birchwood Inn
Hampton Inn & Suites Berkshires Lenox
2.5 out of 5
445 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is $97 per night from Nov 1 to Nov 1
4.6/5 Wonderful! (749 reviews)
"Everything was good. The bed was not comfortable too soft"

Reviewed on Oct 15, 2021

Hampton Inn & Suites Berkshires Lenox
Berkshire Valley Inn
2.5 out of 5
2541 Hancock Rd, Williamstown, MA
The price is $119 per night from Nov 3 to Nov 3
4.5/5 Wonderful! (335 reviews)
"Found location ideal for going north to Williamstown ( check out Para Bistro for dining) or south to Lenox and Lee ( Starving Artist crepes!)"

Reviewed on Oct 18, 2021

Berkshire Valley Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is $160 per night from Nov 1 to Nov 1
4.3/5 Excellent! (482 reviews)
"Red Lion is one of a kind, Sitting on the porch is extremely relaxing."

Reviewed on Sep 28, 2021

The Red Lion Inn
Cozy Corner Motel
2 out of 5
284 Sand Springs Rd. Rte 7, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is $62 per night from Nov 7 to Nov 7
4.3/5 Excellent! (358 reviews)
"Very basic motel but very clean with a lovely friendly staff. It is set back off of a busy street. Very good value."

Reviewed on Oct 14, 2021

Cozy Corner Motel
The Black Swan Lee - Lenox, Ascend Hotel Collection
3 out of 5
435 Laurel St, Lee, MA
Fully refundableReserve now, pay when you stay
The price is $110 per night from Nov 3 to Nov 3
4.3/5 Excellent! (757 reviews)
"Great location, beautiful views, nice rooms, great staff"

Reviewed on Oct 14, 2021

The Black Swan Lee - Lenox, Ascend Hotel Collection
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Hancock, MA
4.2/5 Excellent! (1,437 reviews)
"Very nice property - clean, staff very friendly"

Reviewed on Oct 13, 2021

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Vacation Village in the Berkshires
Conroy's B&B
3.5 out of 5
11 East Street (Route 7), Stockbridge, MA
4.2/5 Excellent! (22 reviews)
"We were informed that the bathroom would be shared; it was unfortunate that there was no private bathroom option."

Reviewed on Oct 6, 2019

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Conroy's B&B
The Orchards Hotel
3.5 out of 5
222 Adams Rd, Williamstown, MA
4.2/5 Excellent! (448 reviews)
"A little dated. Restaurant shut down for renovations, disappointing"

Reviewed on Mar 9, 2020

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The Orchards Hotel
Yankee Inn
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
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The price is $85 per night from Nov 4 to Nov 4
4.2/5 Excellent! (948 reviews)
"Beautiful room and friendly staff, only stayed for one night but it was great and we will be back!"

Reviewed on Oct 20, 2021

Yankee Inn
Jiminy Peak Mountain Resort
3 out of 5
37 Corey Rd, Hancock, MA
The price is $139 per night from Oct 27 to Oct 27
4/5 Very Good! (734 reviews)
"Beautiful area!! Room was clean and comfortable, loved having the kitchenette and sitting area. We went in what I would say was "off" season and the restaurants at the hotel weren't open. Google said they were but they were not. Other than that, beautiful place!"

Reviewed on Oct 9, 2021

Jiminy Peak Mountain Resort
Days Inn by Wyndham Great Barrington
2 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is $67 per night from Nov 1 to Nov 1
3.8/5 Good! (728 reviews)
"A little challenge locating as pix shown is rear view not seen from Main St. # not shown. Too bad local business / restaurant info not available in lobby."

Reviewed on Oct 16, 2021

Days Inn by Wyndham Great Barrington
Berkshire Inn
2 out of 5
150 W Housatonic St, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is $69 per night from Nov 1 to Nov 1
3.7/5 Good! (410 reviews)
"The location is very convenient being so close to downtown Pittsfield and easy to get into the rural surroundings. Room was comfortable, no breakfast at present due to COVID"

Reviewed on Oct 12, 2021

Berkshire Inn
Chesapeake Inn of Lenox
3 out of 5
210 West Street, P.O. Box 1920, Lenox, MA
3.6/5 Good! (8 reviews)
"Very convenient location to arts / outdoors events in Lenox area. Available for one night stay, last minute booking. Host very responsive"

Reviewed on Oct 14, 2019

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Chesapeake Inn of Lenox
Chestnut Lodge
3.5 out of 5
75 Chestnut Street, Lee, MA
1/5 (2 reviews)
Complete Rip Off!
"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 ..."

Reviewed on Aug 14, 2016

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Chestnut Lodge
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