A lake with a rocky shoreline and a forested island.

Find Romantic Hotels in Western Massachusetts from S$128

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Check availability on Western Massachusetts Romantic Hotels

Tonight
26 Oct - 27 Oct
Tomorrow
27 Oct - 28 Oct
This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Western Massachusetts romantic hotels

Two Adirondack chairs facing a river with a forested hill in the background.
A restaurant interior with white tables, cushioned booths, and a bar area.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

1. The Yankee Inn

The Yankee Inn
Lenox
United States
Basil
S$128
includes taxes & fees
27 Oct - 28 Oct
The Yankee Inn
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A dining area with large windows, wooden furniture, and a view of a lake.
A lakeside lodge with a dock, fishing rods, and outdoor seating.
A lakeside dock with kayaks and a covered boat ramp.

2. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Gustavo
S$155
includes taxes & fees
22 Nov - 23 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
An outdoor patio with white chairs and tables, a central fire feature, and string lights.
A hotel with a sign reading "D. HOTEL & SUITES" on the facade.
A hotel room with a striped sofa, a bed with a decorative headboard, a large wall painting, and a sunburst light fixture.
A bar area with a wooden counter, bar stools, and a variety of bottles and glasses.

3. D. Hotel Suites & Spa

D. Hotel Suites & Spa
Holyoke
United States
Devon
S$171
includes taxes & fees
3 Nov - 4 Nov
D. Hotel Suites & Spa
A two-story house with a red door, green shutters, and a snow-covered front yard.
A dining area with round tables, chairs, and a kitchen counter with a refrigerator.
A wooden gazebo with a peaked roof, surrounded by a gravel area with potted plants.
A red building with white trim, surrounded by lush greenery and fruit trees.

4. Centennial House

Centennial House
Northfield
United Kingdom
Alan
S$228
includes taxes & fees
28 Oct - 29 Oct
Centennial House
Dining
Interior
Room
Interior

5. Garden Gables

Garden Gables
Lenox
S$279
includes taxes & fees
27 Oct - 28 Oct
Garden Gables
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
A cozy library with bookshelves, a fireplace, and comfortable seating.
A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

6. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
S$186
includes taxes & fees
1 Nov - 2 Nov
Berkshires Untold
A large, historic building with a prominent tower and a well-lit entrance labeled "Bollywood".
A modern living room with a sofa, armchairs, a coffee table, and a wine rack.
A spacious outdoor seating area with a fire feature, white brick walls, and multiple windows with shutters.
A long dining table set with white tableware, flanked by windows and a skylight.

7. Inn on Boltwood

Inn on Boltwood
Amherst
United States
Mindy
S$294
includes taxes & fees
1 Nov - 2 Nov
Inn on Boltwood
A bedroom with a bed, a nightstand, a lamp, and a window with curtains.
A residential garden with a lawn, a variety of plants, and a pathway.
A two-story house with a front porch, a number 20 sign, and a pathway leading to the entrance.
A living room with two armchairs, a coffee table, a lamp, a mirror, and a chandelier.

8. Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
Liberty Heights
United States
Peter
S$152
includes taxes & fees
28 Oct - 29 Oct
Naomi's Inn Bed & Breakfast
Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.
A row of colorful Victorian-style houses with a prominent red one labeled "PORCHES."
A hallway with a collection of plates on the walls, leading to a staircase.
Two people sitting by a campfire in a wooded area with benches and a clear view of the surrounding trees.

9. The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
North Adams
United States
Ram
S$221
includes taxes & fees
25 Nov - 26 Nov
The Porches Inn at Mass MoCA
A red building with a sign reading "Shaker Mill Inn."
A cozy room with a bed, a sofa, a small table, and a desk. There are two lamps on the bed and a window with curtains.
A covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.
A cozy living room with a sofa, a small table, and a bookshelf. There is a window with curtains, and a painting on the wall.

10. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Mahadeva
S$160
includes taxes & fees
2 Nov - 3 Nov
Shaker Mill Inn
View all properties

Top Western Massachusetts Hotel Reviews

La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

8/10 Good
"The hotel overall was extremely kid friendly. The pool/arcade were amazing. However, not a huge deal the TV kept cutting out no matter what channel it was on. It was annoying. The staff and the clientele were amazing. We go to the area frequently from CT to go to six flags. This is our go to place."
Catherine 1-night trip
Posted 13 hours ago
La Quinta Inn & Suites by Wyndham Springfield MA
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Everything was absolutely perfect! Staff was extremely friendly and the property is so clean and inviting. We loved it so much that we extended our stay!"
Angelina 7-night trip
Posted 14 hours ago
Vacation Village in the Berkshires

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