Find Winery Hotels in Western Massachusetts, MA

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Check availability on Western Massachusetts Winery Hotels

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Compare Western Massachusetts Winery Hotels room rates, reviews, and availability. Most hotels are fully refundable.

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (83)
"Beautiful place to stay "
The price is AED 973
AED 1,175 total
includes taxes & fees
28 Apr - 29 Apr
The Old Inn On The Green

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (409)
"Beautiful room, very clean. breakfast was not what i was expecting, walk way from parking lot covered with ice and snow, very dangerous to walk, needs to be cleaned or at least put some salt on the ground. other then that everything was excellent. will stay again"
The price is AED 533
AED 584 total
includes taxes & fees
29 Apr - 30 Apr
Shaker Mill Inn

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1002)
" It is a fairly modest motel but everything went fine and I felt we got our money's worth. There was just nothing special about it."
The price is AED 368
AED 411 total
includes taxes & fees
28 Apr - 29 Apr
Best Western Plus Berkshire Hills Inn & Suites

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (964)
"The room and bathroom were very clean. "
The price is AED 239
AED 262 total
includes taxes & fees
1 May - 2 May
Pleasant Valley Motel West Stockbridge

Chesapeake Inn of Lenox

3.0 star property
7.4 out of 10, Good, (8)
"Very convenient location to arts / outdoors events in Lenox area. Available for one night stay, last minute booking. Host very responsive"
Chesapeake Inn of Lenox

Monument Mountain Motel

2.5 star property
9.0 out of 10, Wonderful, (708)
"Manager (owner?) was friendly and helpful. Room was clean and spacious (had corner room). Very good for price. Some annoying ticking sound maybe from room heater throughout the night but otherwise no issues at all. Would stay here again."
The price is AED 244
AED 273 total
includes taxes & fees
28 Apr - 29 Apr
Monument Mountain Motel

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (696)
"Stayed a week while working in the area. Staff was super friendly, rooms were clean & quiet, mattresses pretty comfortable. The only thing keeping it from a solid 5 stars was the breakfast is not so good. Watery eggs just aren't my jam. "
The price is AED 555
AED 620 total
includes taxes & fees
26 May - 27 May
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1002)
"Room was clean and the frig was updated to a larger size, which was nice. There is a bit of a danger with the bathtub. It has a high step in and out of the shower/ tub. Pillows were too soft. There was no neck support."
The price is AED 278
AED 310 total
includes taxes & fees
11 May - 12 May
Quality Inn

Lantern House Motel

2.5 star property
8.2 out of 10, Very Good, (455)
"The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should open the windows. How about I decide that? The room was musty-smelling, and everything was very dated and just didn't feel very clean. There are better options in Great Barrington. This is a place to...
Lantern House Motel

Garden Gables Inn

4.0 star property
9.2 out of 10, Wonderful, (57)
"Rosie the Innkeeper was very friendly and welcoming. The breakfast was outstanding and so was our waitress. Can’t wait to go back again. "
Garden Gables Inn
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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