Most Romantic Hotels in Western Massachusetts

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Check availability on Western Massachusetts Romantic Hotels

Our top choices for Western Massachusetts romantic hotels

Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1002)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is RM307
RM343 total
includes taxes & fees
24 Dec - 25 Dec
The Yankee, Trademark Collection by Wyndham
Front of property – evening/night
Inn on Boltwood

Inn on Boltwood

Inn on Boltwood
3.0 star property
Amherst
9.4 out of 10, Exceptional, (749)
"Room was clean and the bed was very comfortable. "
United States
Michael
Inn on Boltwood
Exterior
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"The room was very clean. The bed, linens & towels were exceptional. All of the staff were wonderful. "
United States
Joyce
The price is RM611
RM865 total
includes taxes & fees
12 Jan - 13 Jan 2026
The Red Lion Inn
Indoor pool
D. Hotel Suites & Spa

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2248)
"Stayed 3 nights, really great hotel and value. "
United States
Vince
The price is RM448
RM520 total
includes taxes & fees
1 Jan - 2 Jan 2026
D. Hotel Suites & Spa
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (986)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is RM380
RM424 total
includes taxes & fees
16 Dec - 17 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Front of property – evening/night
The Williams Inn

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (549)
"Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!"
United States
Jon
The price is RM808
RM902 total
includes taxes & fees
14 Dec - 15 Dec
The Williams Inn
Lobby lounge
Berkshires Untold

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (815)
"Easiest check in and out. Great food in dining room. "
United States
William
The price is RM449
RM502 total
includes taxes & fees
16 Dec - 17 Dec
Berkshires Untold
Front of property
Hotel Northampton

Hotel Northampton

Hotel Northampton
3.5 star property
Northampton
9.2 out of 10, Wonderful, (1000)
"Beautiful historic property with great dining options."
United States
Mark
Hotel Northampton
Property amenity
Courtyard by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst
3.0 star property
Hadley
9.0 out of 10, Wonderful, (682)
"Nice and quiet and conveniently located very close to UMass"
United States
Connor
The price is RM586
RM655 total
includes taxes & fees
22 Dec - 23 Dec
Courtyard by Marriott Hadley Amherst
Exterior
Harbour House Inn

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people."
United States
alton
The price is RM881
RM931 total
includes taxes & fees
12 Jan - 13 Jan 2026
Harbour House 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.
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Top Western Massachusetts Hotel Reviews

D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"Stayed 3 nights, really great hotel and value. "
Vince 3-night trip
Posted 2 days ago
D. Hotel Suites & Spa
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"The best of the best A definite destination and accommodations"
Seth 1-night trip
Posted 4 days ago
The Red Lion Inn

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