Search Resort Hotels in Chester from CA $93

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Recommended hotels in Chester

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,002 reviews)
"It was a solid experience at the Best western, staff was super nice, the room was spacious and clean, the breakfast was delicious and the location is superb. Overall it was a great experience and will definitely stay there again "
United States
Kristina
The price is CA $171
CA $191 total
includes taxes & fees
Apr 15 - Apr 16
Best Western Plus Berkshire Hills Inn & Suites

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (838 reviews)
"Nice place and very reasonable for great location "
United States
Raymond
The price is CA $83
CA $93 total
includes taxes & fees
Apr 14 - Apr 15
Monument Mountain Motel

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.6 out of 10, Excellent, (127 reviews)
"Friendly staff, really nice room, quiet. I really enjoyed my stay."
United States
Desiree
The price is CA $149
CA $166 total
includes taxes & fees
Apr 22 - Apr 23
River Valley Inn

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (890 reviews)
"This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again."
United States
Payton
The price is CA $129
CA $144 total
includes taxes & fees
Apr 9 - Apr 10
Berkshires Untold

Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western
2.5 star property
West Springfield
7.8 out of 10, Good, (159 reviews)
"So close to the Big E Fairgroynds, wonderful service, would stay again!"
United States
Terry
The price is CA $141
CA $161 total
includes taxes & fees
Apr 26 - Apr 27
Baldwin Inn & Suites, SureStay Collection by Best Western

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2,231 reviews)
"Very clean, comfortable, and quiet hotel. We enjoyed our visit."
United States
Larry
The price is CA $171
CA $199 total
includes taxes & fees
Apr 21 - Apr 22
D. Hotel Suites & Spa

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (555 reviews)
"Clean … check in , good location for us .. we’ll be back in Maynn"
United States
Kathleen
The price is CA $153
CA $171 total
includes taxes & fees
Apr 15 - Apr 16
The Little Lion

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is CA $199
CA $222 total
includes taxes & fees
Apr 15 - Apr 16
Element Lenox Berkshires

TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
3.0 star property
Hadley
9.8 out of 10, Exceptional, (77 reviews)
"The check in staff were amazing "
United States
mandeep
The price is CA $212
CA $236 total
includes taxes & fees
Apr 15 - Apr 16
TownePlace Suites by Marriott Hadley Amherst

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,000 reviews)
"Great visit all around. Centrally located to the skiing resorts, lots to do in town, decent breakfast spread, clean room, and for a short stay, housekeeping came when unexpected! "
United States
Amy
The price is CA $141
CA $157 total
includes taxes & fees
Apr 21 - Apr 22
Quality Inn Lee - Lenox South

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (431 reviews)
"Breakfast was exceptional. We couldn’t have been happier during our stay."
United States
Robert
The price is CA $156
CA $177 total
includes taxes & fees
Apr 12 - Apr 13
Naomi's Inn Bed & Breakfast

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (896 reviews)
"Overall pleasant stay; great facilities, staff, and location"
United States
Casey
The price is CA $121
CA $166 total
includes taxes & fees
May 7 - May 8
Berkshire Mountain Lodge

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,002 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is CA $99
CA $108 total
includes taxes & fees
Apr 15 - Apr 16
Pleasant Valley Motel West Stockbridge

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (575 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is CA $104
CA $117 total
includes taxes & fees
Apr 8 - Apr 9
Travelodge by Wyndham Great Barrington Berkshires

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (840 reviews)
"We had an excellent experience all around. "
United States
Jennifer
The price is CA $164
CA $183 total
includes taxes & fees
Apr 19 - Apr 20
Hampton Inn Westfield

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (754 reviews)
"Staff was great! Clean room, parking was always available. Breakfast was great. Had a great time!"
United States
Brigid
The price is CA $160
CA $179 total
includes taxes & fees
Apr 20 - Apr 21
Holiday Inn Express Hotel & Suites Great Barrington by IHG

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,003 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
The price is CA $144
CA $161 total
includes taxes & fees
Apr 29 - Apr 30
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,005 reviews)
"Best hotel in area."
United States
William
The price is CA $147
CA $167 total
includes taxes & fees
Apr 21 - Apr 22
Tru by Hilton Chicopee Springfield

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (625 reviews)
"We enjoyed our 3 nights it was quiet and very clean "
United States
Joanne
The price is CA $170
CA $190 total
includes taxes & fees
May 4 - May 5
Fairfield Inn & Suites Springfield Holyoke

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (919 reviews)
"Everything clean "
United States
GLADYS
The price is CA $130
CA $145 total
includes taxes & fees
May 3 - May 4
Quality Inn Westfield - Springfield
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Top Chester Hotel Reviews

Find out more about Chester

Chester Resorts information

Number of reviews
13,954
Accommodation
8 Resorts
Lowest Price
CA $93
Highest Price
CA $236

Frequently asked questions

What is Chester like for a resort vacation?
You deserve to get away, and a resort is the ideal place to find all the amenities and services you need for a relaxing stay in Chester. One of the comfortable resorts in the area might be just what you're looking for, whether you're hoping for great restaurants on site, a state-of-the-art fitness center, or activities for the kids.
What's the best resort for my stay in Chester?
Our highest-rated resort near Chester: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 15 mi (24.1 km) from Chester. Enjoy the sauna, fitness center, and terrace.
What can I do in Chester?
Experience the local theater scene at Chester Town Hall, or bring the kids to Berkshire Scenic Railway Museum for some family fun. In the area, other attractions include Pyramid Lake and Skyline Trail.
What's the weather like in Chester?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Chester are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.
What's the best way to get to and around Chester?
Fly into Westfield, MA (BAF-Barnes Municipal), which is located 15.4 mi (24.7 km) from the heart of the city. You can also search for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 18.9 mi (30.4 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

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