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
12 Oct - 13 Oct
Tomorrow
13 Oct - 14 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 lodge with a large building and a dock by a lake, surrounded by forest.
A lakeside dock with kayaks and a covered boat ramp.
A dining area with large windows, wooden furniture, and a view of a lake.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Bob
£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.
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.
A hotel room with a desk, chair, lamp, and a large mirror. There is a staircase leading to an outdoor area with a railing.

2. Hotel Northampton

Hotel Northampton
Northampton
United States
Beth
£125
includes taxes & fees
13 Oct - 14 Oct
Hotel Northampton
An outdoor patio with white chairs and tables, a central fire feature, and string lights.
A bedroom with a four-poster bed, a leather sofa, a wooden coffee table, and a view of greenery through the window.
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.

3. D. Hotel Suites & Spa

D. Hotel Suites & Spa
Holyoke
United States
Jim
£108
includes taxes & fees
26 Oct - 27 Oct
D. Hotel Suites & Spa
An outdoor patio area with seating, a fire feature, and a view of the building's exterior.
A hotel room with two beds, a large window with a view of trees, and a wall mural.
A modern reception area with a wooden reception desk, seating area with sofas and chairs, and large windows providing natural light.
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 grassy outdoor area with four blue Adirondack chairs arranged in a circle.
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.

5. East Rock Inn

East Rock Inn
Great Barrington
United States
ERIK
£106
includes taxes & fees
11 Nov - 12 Nov
East Rock Inn
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.
A dining table set with a vase of flowers, a book, and cutlery.
A bed with a white lace bedspread, a tray with cookies and a bottle, and two glasses of red wine.
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 narrow hallway with two beverage dispensers and a snack shelf.
A spacious dining area with multiple tables and chairs, a sofa, and patterned curtains.
A reception area with a wooden reception desk, framed pictures on the wall, a small plant, and a hallway leading to an exit.

7. Hampton Inn & Suites Springfield/Downtown

Hampton Inn & Suites Springfield/Downtown
South End
United States
James
£99
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 lobby with a reception desk, seating area, and a large aquarium.
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.

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 pond with a stone border, surrounded by lush greenery and trees.
A wooden deck with a green metal table and chairs, surrounded by a wooden railing.
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
13 Oct - 14 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 cabin in a forest with a dirt path leading to it, surrounded by trees.
A triangular-shaped building with a balcony and a wooden picnic table in front.
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

Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"First, this is an absolutely gorgeous place! The outside areas are beautiful with comfy furniture, flowers and fire pits. Inside is a small intimate restaurant and bar, plus sitting area. With books and plants, very nice. We had dinner there which was excellent, and loved cocktails and sunset outside by the fire pits. When we checked in, we were assigned one of their premium rooms, which sounded great. However, it was on the second floor, at the very end of a long outside corridor, accessible only by stairs near the lobby. There is no elevator. We did go to the room, lugging our bags and a cooler. Unpleasant, as we are somewhat older. We concluded that we did not want to be that far from the main area, so asked to be moved, and were accommodated. We found the new room the same, but lacking a luggage rack and a coffee service (those were only available in the premium rooms at the end of the long corridor). We were given a luggage rack, and complimentary coffee was available in the restaurant in the morning, but it seemed odd that those were considered premium in such a nice place. Otherwise we loved the hotel, room was very nice with a comfortable bed and a very updated bath with a walk in shower. The real star of the hotel is the lobby restaurant and outdoor space - that was just perfect!"
William 1-night trip
Posted 14 hours ago
Quality Inn Great Barrington

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