Fall Season in Western Massachusetts

Winery Hotels & Resorts in Western Massachusetts from AU$196

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Check availability on Western Massachusetts Winery Hotels

Our top choices for Western Massachusetts hotels with winery

Terrace/patio

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2,205 reviews)
"Breakfast was excellent."
United States
Candyce
The price is AU$202
includes taxes & fees
21 June - 22 June
D. Hotel Suites & Spa
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,004 reviews)
"Great breakfast and coffe is available 24 hours. Nice location to near by restaurants and great view by water."
United States
andrew
The price is AU$227
includes taxes & fees
15 June - 16 June
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Front of property

Hotel Northampton

Hotel Northampton
3.5 star property
Northampton
9.2 out of 10, Wonderful, (1,004 reviews)
"Great location and I had a room with a private deck."
United States
Jonathan
The price is AU$236
includes taxes & fees
14 June - 15 June
Hotel Northampton
Classic Double Room, 2 Queen Beds, Courtyard View | Bathroom

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.4 out of 10, Exceptional, (47 reviews)
"The East Rock Inn is great. It's comfortable, clean and close to downtown Great Barrington. This was my second time staying here."
United States
Laura
The price is AU$210
includes taxes & fees
24 June - 25 June
East Rock Inn
Lobby

Hampton Inn & Suites Springfield/Downtown

Hampton Inn & Suites Springfield/Downtown
2.5 star property
South End
8.6 out of 10, Excellent, (1,001 reviews)
"The room was very clean staff was very nice and the breakfast was very good."
United States
Michele
The price is AU$196
includes taxes & fees
6 July - 7 July
Hampton Inn & Suites Springfield/Downtown
Free daily on-the-go breakfast

Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst
2.5 star property
Northampton
7.2 out of 10, Good, (1,007 reviews)
"Recently renovated Very helpful staff"
United States
Lois
The price is AU$196
includes taxes & fees
1 July - 2 July
Quality Inn & Suites Northampton - Amherst
Exterior

Berkshire Valley Inn

Berkshire Valley Inn
2.5 star property
Williamstown
9.2 out of 10, Wonderful, (570 reviews)
"Innkeeper is friendly and the place was fairly clean. Lovely to have coffee and complimentary breakfast on site. Rooms (especially the bathrooms and baseboard heaters) are somewhat dated and could use a refresh. Visited during a chilly time of the year and thermostat was tricky to operate. Heat was set not to go above 75 degrees, which was less than ideal."
United States
Henrietta
The price is AU$248
includes taxes & fees
18 June - 19 June
Berkshire Valley Inn
View from property

Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield
3.0 star property
West Springfield
9.2 out of 10, Wonderful, (639 reviews)
"Great location and the room was big and spotless."
United States
Carlos
The price is AU$220
includes taxes & fees
2 July - 3 July
Courtyard by Marriott West Springfield
Front of property

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (165 reviews)
"Lovely stay!"
United States
Jiacheng
The price is AU$303
includes taxes & fees
11 June - 12 June
Brook Farm Inn
Interior

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
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$495
includes taxes & fees
11 June - 12 June
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
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

The Yankee Inn

The Yankee Inn

10/10 Excellent
"I got the impression that Yankee Inn has quite a history, although it has been recently updated and renovated. The staff were available and friendly. At times I felt I was on a 1950s movie set, imagining Bing Crosby singing in my head. I ultimately extended my stay because it's location was a hub for the many surrounding activities--it's slightly over an hour drive to Hartford, and I was happy to leave the hustle and bustle of the city and return to the beauty of the Berkshires. I was surrounded by nature, but a grocery store, pharmacy, laundromat, and stores were also a short distance down the road. An extensive daily breakfast selection surpassed any I've recently had, and I've done my fair share of traveling."
Rachel 1-night trip
Posted 2 days ago
The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Excellent location, great low price, VERY Comfortable bed- throwback era motel. Why pay more when it’s all here!"
Alan 1-night trip
Posted 3 days ago
Quality Inn Great Barrington

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