Best Resorts in Chester

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
$109 nightly
The price is $122
May 26 - May 27
Total with taxes and fees
The Yankee Inn
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

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
$108 nightly
The price is $121
May 28 - May 29
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Standard Room, 2 Queen Beds, Non Smoking | Pillowtop beds, desk, laptop workspace, blackout drapes

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
$111 nightly
The price is $127
May 31 - Jun 1
Total with taxes and fees
Baldwin Inn & Suites, SureStay Collection by Best Western
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
$111 nightly
The price is $124
May 28 - May 29
Total with taxes and fees
Berkshire Mountain Lodge
Studio Suite, Multiple Beds | Desk, laptop workspace, free WiFi, bed sheets

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
$105 nightly
The price is $117
Jun 4 - Jun 5
Total with taxes and fees
River Valley Inn
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
$125 nightly
The price is $140
May 28 - May 29
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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
$89 nightly
The price is $102
Jun 9 - Jun 10
Total with taxes and fees
Hampton Inn West Springfield
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
$110 nightly
The price is $122
Jun 15 - Jun 16
Total with taxes and fees
Quality Inn Lee - Lenox South
Lobby

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,003 reviews)
"It was a great stay."
United States
Geovani
$114 nightly
The price is $129
May 31 - Jun 1
Total with taxes and fees
Tru by Hilton Chicopee Springfield
Room, 2 Queen Beds, Refrigerator | Premium bedding, desk, laptop workspace, blackout drapes

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
$125 nightly
The price is $139
May 31 - Jun 1
Total with taxes and fees
Hampton Inn Westfield
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (955 reviews)
"Great stay!"
United States
Aditya
$111 nightly
The price is $124
May 25 - May 26
Total with taxes and fees
Berkshires Untold
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

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
$76 nightly
The price is $85
May 25 - May 26
Total with taxes and fees
Monument Mountain Motel
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
$213 nightly
The price is $238
May 25 - May 26
Total with taxes and fees
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
View from property

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (643 reviews)
"The staff is amazing here. So friendly, caring and helpful. The hotel is clean and fresh smelling. "
United States
Jennifer
$127 nightly
The price is $142
Jun 23 - Jun 24
Total with taxes and fees
Fairfield Inn & Suites Springfield Holyoke
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
$98 nightly
The price is $109
Jun 14 - Jun 15
Total with taxes and fees
Quality Inn Westfield - Springfield
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
$74 nightly
The price is $82
May 28 - May 29
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (561 reviews)
"Avoid this place."
United States
Carole
$93 nightly
The price is $104
Jun 11 - Jun 12
Total with taxes and fees
The Little Lion
Room (Louis XIV) | Individually decorated, individually furnished, iron/ironing board

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
$118 nightly
The price is $134
May 25 - May 26
Total with taxes and fees
Naomi's Inn Bed & Breakfast
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
$116 nightly
The price is $130
Jun 1 - Jun 2
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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
$73 nightly
The price is $81
May 25 - May 26
Total with taxes and fees
Berkshire 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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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 10 hours ago
Berkshires Untold

Find out more about Chester

Chester Resorts information

Number of reviews
12,368
Accommodation
8 Resorts
Lowest Price
$81
Highest Price
$238

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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