Find Winery Hotels in Western Massachusetts, MA

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check availability on Western Massachusetts Winery Hotels

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 SAR 1,088
SAR 1,313 total
includes taxes & fees
4 May - 5 May
The Old Inn On The Green

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (410)
"Nice"
Shaker Mill Inn

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1001)
"Friendly check in and nice hotel "
The price is SAR 376
SAR 420 total
includes taxes & fees
4 May - 5 May
Best Western Plus Berkshire Hills Inn & Suites

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (965)
"Easy access to the Massachusetts Turnpike and less than 10 miles away from the tourist options I selected."
The price is SAR 244
SAR 268 total
includes taxes & fees
8 May - 9 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, (710)
"Nice place and surrounding area "
The price is SAR 285
SAR 318 total
includes taxes & fees
8 May - 9 May
Monument Mountain Motel

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (697)
"Nice property right in town. Close to shops and restaurants "
The price is SAR 566
SAR 633 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, (1001)
"Great place to stay. Clean rooms, quiet area"
The price is SAR 284
SAR 317 total
includes taxes & fees
15 May - 16 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.
Don't see what you're looking for?
See all available properties in Western Massachusetts