Photo by Ed Gaffny

Find 4 Star Hotels in Cheshire, MA from SAR 388

  • 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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check availability on Cheshire 4 Star Hotels

Compare Cheshire 4 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

The Williams Inn
Front of property - evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (449)
"Great location and nice accommodations."
The price is SAR 998
SAR 1,115 total
includes taxes & fees
13 May - 14 May
The Williams Inn
Lakehouse Inn
Aerial view

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (257)
"Wonderful Location"
The price is SAR 728
SAR 853 total
includes taxes & fees
25 May - 26 May
Lakehouse Inn
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (279)
"The big plus about the whole stay was "
The price is SAR 388
SAR 434 total
includes taxes & fees
25 May - 26 May
The Central Downtown Inn & Suites
33 Main
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

4.0 star property
10.0 out of 10, Exceptional, (70)
"Beautiful place. Everything was perfect and so pretty. Great location, too. Will definitely return. "
The price is SAR 1,471
SAR 1,644 total
includes taxes & fees
15 May - 16 May
33 Main
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (125)
"Very enjoyable comfortable stay"
The price is SAR 1,009
SAR 1,127 total
includes taxes & fees
14 May - 15 May
Devonfield Inn B&B
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business center

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is SAR 2,584
SAR 3,126 total
includes taxes & fees
15 May - 16 May
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Seven Hills Inn
Terrace/patio

Seven Hills Inn

4.0 star property
7.8 out of 10, Good, (467)
"Great location, nice breakfast and clean rooms"
Seven Hills Inn
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"We we were in the Out of Africa room, set apart in a complex of 4 suites in a unit apart from the Inn itself. The room was uniquely created to feel like an escape to Africa, and heated by a lovely gas fireplace. The breakfast both mornings, delicious. A perfect getaway!"
The Inn at Stockbridge
Hampton Terrace Inn
Seasonal outdoor pool

Hampton Terrace Inn

4.0 star property
9.0 out of 10, Wonderful, (42)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
Hampton Terrace Inn
General Williams Estate House Lenox/Stockbridge
Exterior

General Williams Estate House Lenox/Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (110)
"The house was beautiful, the outdoor space was gorgeous, and the pool was amazing! I highly recommend this charming spot."
General Williams Estate House Lenox/Stockbridge
Garden Gables Inn
Front of property - evening/night

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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking, and lake views.

See all hotels in Cheshire
The road less traveled sometimes is absolutely beautiful. In a month this will be a great spot for Autumn. I will repost the exact same foliage shot and see if I am correct. Excited to do it actually..
Photo by Ed Gaffny
Open Photo by Ed Gaffny