A lake with a rocky shoreline and a forested island.

Search Winery Hotels in Western Massachusetts

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Check availability on Western Massachusetts Winery Hotels

Tonight
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Western Massachusetts hotels with winery

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 lodge with a large building and a dock by a lake, surrounded by forest.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Gustavo
£97
includes taxes & fees
8 Nov - 9 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A multi-story hotel with a prominent "Hotel Northampton" sign, featuring a classic architectural style with a brick facade and multiple windows.
A hotel room with a desk, chair, lamp, and a large mirror. There is a staircase leading to an outdoor area with a railing.
An outdoor cafe with tables and chairs, surrounded by hanging flower baskets and a brick building in the background.
A hotel lobby with a glass vase of white flowers on a table, red chairs, and a wooden reception desk.

2. Hotel Northampton

Hotel Northampton
Northampton
United States
Beth
£125
includes taxes & fees
14 Oct - 15 Oct
Hotel Northampton
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 bar area with a wooden counter, bar stools, and a variety of bottles and glasses.
A hotel with a sign reading "D. HOTEL & SUITES" on the facade.

3. D. Hotel Suites & Spa

D. Hotel Suites & Spa
Holyoke
United States
Jim
£108
includes taxes & fees
28 Oct - 29 Oct
D. Hotel Suites & Spa
An outdoor patio area with seating, a fire feature, and a view of the building's exterior.
A modern reception area with a wooden reception desk, seating area with sofas and chairs, and large windows providing natural light.
A hotel room with two beds, a large window with a view of trees, and a wall mural.
A modern bar area with a long counter, multiple screens, and a seating area with metal chairs.

4. Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield
West Springfield
United States
Amy
£113
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott West Springfield
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.
A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A sign for East Rock Inn with a mountainous logo, surrounded by lush greenery and a gravel path leading to a building.

5. East Rock Inn

East Rock Inn
Great Barrington
United States
ERIK
£108
includes taxes & fees
12 Nov - 13 Nov
East Rock Inn
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.
A bed with a white lace bedspread, a tray with cookies and a bottle, and two glasses of red wine.
A cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.
A loft bedroom with a sloped ceiling, a ceiling fan, a floor lamp, a bed with a patterned bedspread, a chair, and a small table.

6. Brook Farm Inn

Brook Farm Inn
Lenox
United States
Carrie
£170
includes taxes & fees
2 Nov - 3 Nov
Brook Farm Inn
An indoor swimming pool with a pool lift, a changing room, and a view of the outside.
A reception area with a wooden reception desk, framed pictures on the wall, a small plant, and a hallway leading to an exit.
A hotel room with two beds, a desk with a flat-screen TV, a chair, and a bedside table with lamps.
A spacious dining area with multiple tables and chairs, a sofa, and patterned curtains.

7. Hampton Inn & Suites Springfield/Downtown

Hampton Inn & Suites Springfield/Downtown
South End
United States
James
£98
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn & Suites Springfield/Downtown
A modern restaurant with high tables and bar stools, a fireplace, and a TV mounted on the wall.
A room with a grey sofa, a small table, a lamp, a door, and a framed abstract artwork on the wall.
A hotel room with two beds, a microwave, a small table with a phone and a coffee maker, a sink, and a large window with curtains.
A vending machine stocked with snacks and beverages, and shelves with packaged goods.

8. Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst
Northampton
United Kingdom
Glenn
£103
includes taxes & fees
8 Nov - 9 Nov
Quality Inn & Suites Northampton - Amherst
A cozy room with two beds, large windows, and a view of a snowy landscape.
A wooden deck with a green metal table and chairs, surrounded by a wooden railing.
A pond with a stone border, surrounded by lush greenery and trees.
A building with a covered outdoor area, a railing, and a Christmas tree.

9. The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
United States
Paula
£206
includes taxes & fees
14 Oct - 15 Oct
The Creation Station is a cozy place so make yourself at home.
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.
A triangular-shaped building with a balcony and a wooden picnic table in front.
A cozy living room with a grey sofa, a patterned throw blanket, and a wooden ceiling.
A cozy interior with a loft bed, a small kitchenette, and a welcoming 'Welcome' mat.

10. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
United States
Sharon K.
£282
includes taxes & fees
14 Oct - 15 Oct
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
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Top Western Massachusetts Hotel Reviews

The Yankee Inn

The Yankee Inn

8/10 Good
"Everything at the Yankee Inn was very good with the exception of, wasn’t the most comfortable bed I’ve ever slept in, but everything else was very good"
Mark 1-night trip
Posted 5 hours ago
The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Beds were comfortable, room was clean, train was not often"
Patricia 3-night trip
Posted 6 hours ago
Quality Inn Great Barrington

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