A person snowboarding down a snowy slope.

Find Romantic Hotels in The Berkshires, MA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Romantic Hotels

Our top choices for The Berkshires romantic hotels

Front of property - evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (139 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is AED 1,612
AED 1,801 total
includes taxes & fees
21 Jul - 22 Jul
Devonfield Inn B&B
Desk, laptop workspace, iron/ironing board (on request), WiFi (free)

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (102 reviews)
"Beautiful home with warm and friendly hosts. The rooms were tastefully designed, the bed was very comfortable and the large bathroom was luxurious. The breakfast was absolutely delicious. We will definitely stay again next time we are in Great Barrington. "
United States
Nicole
The price is AED 826
AED 923 total
includes taxes & fees
27 Jul - 28 Jul
Granville House
Luxury Room, 1 King Bed, Bathtub | Premium bedding, iron/ironing board, WiFi (free), individually decorated

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is AED 2,748
AED 3,069 total
includes taxes & fees
16 Aug - 17 Aug
33 Main
Exterior

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (220 reviews)
"Great facilities, fantastic views and neighborhood. Everything is so neat and clean. Live it and will come back."
United States
Meng
The price is AED 873
AED 923 total
includes taxes & fees
21 Jul - 22 Jul
Blue Vista Motor Lodge
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (99 reviews)
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
United States
Stephen
The price is AED 1,362
AED 1,597 total
includes taxes & fees
27 Jul - 28 Jul
The Inn at Stockbridge
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (58 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is AED 701
AED 783 total
includes taxes & fees
27 Jul - 28 Jul
Wilder House Berkshires
Exterior

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.8 out of 10, Exceptional, (35 reviews)
"Great stay!"
United States
Conor
The price is AED 1,537
AED 1,840 total
includes taxes & fees
19 Aug - 20 Aug
Prospect Berkshires
Lobby

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (28 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is AED 841
AED 940 total
includes taxes & fees
27 Jul - 28 Jul
Element by Marriott Lenox Berkshires
Property entrance

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (877 reviews)
"Beautiful room with an amazing lobby."
United States
Dragana
The price is AED 915
AED 1,022 total
includes taxes & fees
29 Jul - 30 Jul
Hotel On North
Property grounds

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (624 reviews)
"I was very satisfied with the stay. The room was extremely clean and comfortable. The outdoor space was very pleasant and peaceful; a beautiful setting. The staff was courteous and helpful."
United States
james
The price is AED 511
AED 570 total
includes taxes & fees
21 Jul - 22 Jul
Maple Terrace Motel
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 The Berkshires Hotel Reviews

The Red Lion Inn

The Red Lion Inn

8/10 Good
"Dinner in the main dining room was amazing! Food delicious and staff attentive. We stayed in the Stephen’s House and arrived in the dark. It was not well lighted and 184 was up a huge flight of stairs. We had to haul up too many bags! We would have done a sm. 1 night bag If we had known this was a second floor. Beds were very uncomfortable soft and towels with stains. The kitchen area was without a refrigerator turned on and no ice. The front desk attendant was very efficient and ran some ice over! We love Red Lion Inn and found some things a bit off this time."
Patricia 1-night trip
Posted 21 hours ago
The Red Lion Inn

Explore a world of travel with Expedia