Search Resort Hotels in Chester from CA $106

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Check prices for these dates

Next weekend
May 29 - May 31
In two weeks
Jun 5 - Jun 7
In one month
Jun 19 - Jun 21
In two months
Jul 17 - Jul 19
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"Breakfast ok, coffee good, staff great"
United States
Peter
The price is CA $176
CA $197 total
includes taxes & fees
Jun 16 - Jun 17
The Yankee Inn
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

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, (1,001 reviews)
"Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant. "
United States
Melinda
The price is CA $152
CA $170 total
includes taxes & fees
May 25 - May 26
Best Western Plus Berkshire Hills Inn & Suites
Terrace/patio

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2,199 reviews)
"Spacious room, very helpful staff, good coffee and an excellent breakfast."
United States
Clifford
The price is CA $115
CA $135 total
includes taxes & fees
May 31 - Jun 1
D. Hotel Suites & Spa
Apartment (0 Bedroom) | Interior

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
3.0 star property
Holyoke
The price is CA $95
CA $327 total
includes taxes & fees
May 26 - May 27
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (946 reviews)
"Clean and great job staffing "
United States
Pedro
The price is CA $121
CA $166 total
includes taxes & fees
May 25 - May 26
Berkshire Mountain Lodge
Room, 2 Queen Beds, Non Smoking

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (856 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is CA $95
CA $106 total
includes taxes & fees
May 31 - Jun 1
Monument Mountain Motel
Standard Room, 2 Queen Beds, Non Smoking

Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western
2.5 star property
West Springfield
8.0 out of 10, Very good, (187 reviews)
"Front desk staff was very friendly and informative. Great location for the local colleges."
United States
Chris
The price is CA $152
CA $174 total
includes taxes & fees
Jun 7 - Jun 8
Baldwin Inn & Suites, SureStay Collection by Best Western
Lobby

Hampton Inn West Springfield

Hampton Inn West Springfield
2.5 star property
West Springfield
8.2 out of 10, Very good, (1,002 reviews)
"The breakfast was great! The rooms and hallways could be cleaner."
United States
Rasha
The price is CA $128
CA $147 total
includes taxes & fees
Jun 9 - Jun 10
Hampton Inn West Springfield
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (955 reviews)
"Great stay!"
United States
Aditya
The price is CA $173
CA $193 total
includes taxes & fees
May 25 - May 26
Berkshires Untold
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (96 reviews)
"This is a great hotel-super clean, nice breakfast, staff very pleasant and helpful. Close to Pittsfield but quieter. Pool and hot tub were great. Highly recommend staying here if you’re in the area."
United States
Kathleen
The price is CA $181
CA $202 total
includes taxes & fees
May 27 - May 28
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
In-room safe, desk, free cribs/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (580 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
The price is CA $104
CA $116 total
includes taxes & fees
May 25 - May 26
Travelodge by Wyndham Great Barrington Berkshires
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,002 reviews)
"Great location "
United States
Edith
The price is CA $156
CA $174 total
includes taxes & fees
May 31 - Jun 1
Quality Inn Lee - Lenox South
Studio Suite, Multiple Beds

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.6 out of 10, Excellent, (156 reviews)
"Friendly staff, great under the radar spot alternative to chain motels!"
United States
Anthony
The price is CA $161
CA $180 total
includes taxes & fees
Jun 3 - Jun 4
River Valley Inn
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (856 reviews)
"Clean comfortable room. Very nice staff. Close to everything in downtown Pittsfield. This is the only place I stay when I’m in Pittsfield. Very peaceful. Excellent place to relax. "
United States
Jennifer
The price is CA $103
CA $115 total
includes taxes & fees
May 25 - May 26
Berkshire Inn
Room (Louis XIV)

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.2 out of 10, Wonderful, (441 reviews)
"He room was very clean, the staff was engaging and the breakfast was delicious. "
United States
John
The price is CA $163
CA $184 total
includes taxes & fees
Jun 18 - Jun 19
Naomi's Inn Bed & Breakfast
Free daily buffet breakfast

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (932 reviews)
"Very clean& maintained. Most comfortable bed I've slept in"
United States
Keith
The price is CA $134
CA $150 total
includes taxes & fees
Jun 14 - Jun 15
Quality Inn Westfield - Springfield
BBQ/picnic area

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.0 out of 10, Very good, (2 reviews)
"After a little snafu with check-in (we had completed the form in advance and never received the room number text), we were able to get checked in with the virtual front desk. The inn was clean and well appointed and centrally located. The common areas felt inviting and useful for both the adults and kids. We would stay again."
United States
Samantha
The price is CA $153
CA $171 total
includes taxes & fees
Jun 9 - Jun 10
Hideaway Inn Lenox
View from property

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (644 reviews)
"The staff is amazing here. So friendly, caring and helpful. The hotel is clean and fresh smelling. "
United States
Jennifer
The price is CA $181
CA $202 total
includes taxes & fees
Jun 22 - Jun 23
Fairfield Inn & Suites Springfield Holyoke
Room, 2 Queen Beds, Refrigerator

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (860 reviews)
"very friendly, room was nice and breakfast was great"
United States
Lawrence
The price is CA $169
CA $189 total
includes taxes & fees
May 31 - Jun 1
Hampton Inn Westfield
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,005 reviews)
"Clean rooms and lovely view"
Canada
Laraib
The price is CA $171
CA $191 total
includes taxes & fees
May 28 - May 29
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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 Chester Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"The room is always clean. We enjoy our stay here every time we visit the Berkshires. We also love the food they serve in the motel restaurant. We love how clean and modern the property looks. Would come back here again when we visit Massachusetts."
Preeyus 2-night trip
Posted 16 hours ago
Berkshires Untold

Find out more about Chester

Chester Resorts information

Number of reviews
13,866
Accommodation
8 Resorts
Lowest Price
CA $106
Highest Price
CA $327

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 top-rated resort near Chester: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 15 mi (24.1 km) from Chester. Has a sauna, a fitness center, and a terrace.
What can I do in Chester?
Experience the local theater scene at Chester Town Hall, or bring the kids to Ashintully Gardens for some family fun. In the area, other attractions include Glendale Falls and Pyramid Lake.
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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