A lake with a rocky shoreline and a forested island.

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Check availability on Western Massachusetts Romantic Hotels

Tonight
Oct 10 - Oct 11
Tomorrow
Oct 11 - Oct 12
Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

Our top choices for Western Massachusetts romantic hotels

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
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
₩142,068
₩158,690 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A two-story house with a red door, green shutters, and a snow-covered front yard.
A group of women in formal attire standing in a garden with a house in the background.
A golf course with a brick pathway, wooden boxes, and a tee box.
A red building with white trim, surrounded by lush greenery and fruit trees.

2. Centennial House

Centennial House
Northfield
United Kingdom
Alan
₩240,548
₩254,259 total
includes taxes & fees
Oct 26 - Oct 27
Centennial House
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 dock with kayaks and a covered boat ramp.
A lakeside lodge with a dock, fishing rods, and outdoor seating.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Bob
₩157,212
₩175,606 total
includes taxes & fees
Nov 10 - Nov 11
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 room with a striped sofa, a bed with a decorative headboard, a large wall painting, and a sunburst light fixture.
A hotel with a sign reading "D. HOTEL & SUITES" on the facade.
A bar area with a wooden counter, bar stools, and a variety of bottles and glasses.

4. D. Hotel Suites & Spa

D. Hotel Suites & Spa
Holyoke
United States
Jim
₩163,022
₩190,754 total
includes taxes & fees
Oct 26 - Oct 27
D. Hotel Suites & Spa
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".

5. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
₩174,487
₩194,902 total
includes taxes & fees
Nov 8 - Nov 9
Berkshires Untold
A large, historic building with a prominent tower and a well-lit entrance labeled "Bollywood".
A long dining table set with white tableware, flanked by windows and a skylight.
A spacious outdoor seating area with a fire feature, white brick walls, and multiple windows with shutters.
A spacious living room with a fireplace, comfortable seating, and elegant chandeliers.

6. Inn on Boltwood

Inn on Boltwood
Amherst
United States
pam
₩276,627
₩309,001 total
includes taxes & fees
Nov 1 - Nov 2
Inn on Boltwood
Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.
Two people sitting by a campfire in a wooded area with benches and a clear view of the surrounding trees.
A hallway with a collection of plates on the walls, leading to a staircase.
A cozy living room with a fireplace, a red armchair, a bookshelf, and a coffee table.

7. The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
North Adams
United States
Ram
₩199,123
₩252,362 total
includes taxes & fees
Nov 10 - Nov 11
The Porches Inn at Mass MoCA
A red building with a sign reading "Shaker Mill Inn."
A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.
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.

8. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Steven
₩174,234
₩191,135 total
includes taxes & fees
Nov 10 - Nov 11
Shaker Mill Inn
A bedroom with a bed, a nightstand, a lamp, and a window with curtains.
A two-story house with a front porch, a number 20 sign, and a pathway leading to the entrance.
A residential garden with a lawn, a variety of plants, and a pathway.
A living room with two armchairs, a coffee table, a lamp, a mirror, and a chandelier.

9. Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
Liberty Heights
United States
Peter
₩140,727
₩159,665 total
includes taxes & fees
Oct 18 - Oct 19
Naomi's Inn Bed & Breakfast
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A covered porch with wicker furniture and hanging flower baskets.
A bar with wooden floors and shelves filled with bottles.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

10. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
₩211,118
₩302,403 total
includes taxes & fees
Nov 3 - Nov 4
The Red Lion Inn
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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 staff was excellent and very friendly. Always greeted me when I came in the hotel, so the acknowledgement was nice. The room was very clean, but the rug in the hallway had a musty smell to it."
Leslie 2-night trip
Posted 1 hour ago
La Quinta Inn & Suites by Wyndham Springfield MA
D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"I love this hotel. The fall decorations are adorable. When I checked in the room was clean but there had obviously been a work crew in the bathroom caulking and hadn’t fully cleaned up. I alerted the front desk and was immediately moved to a lovely cleaned suite. The onsite restaurant is also great."
Marissa 1-night trip
Posted 12 hours ago
D. Hotel Suites & Spa
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"
Joanne 1-night trip
Posted 4 days ago
The Red Lion Inn

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