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Best Resorts in Chester

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Check prices for these dates

Next weekend
Jul 17 - Jul 19
In two weeks
Jul 24 - Jul 26
In one month
Aug 7 - Aug 9
In two months
Sep 4 - Sep 6
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (846 reviews)
"Plenty of parking. Staff was friendly"
United States
William
$61 nightly
The price is $69
Jul 8 - Jul 9
Total with taxes and fees
FairBridge Inn Express
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, (1,006 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
$151 nightly
The price is $169
Jul 8 - Jul 9
Total with taxes and fees
The Yankee Inn
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
7.8 out of 10, Good, (224 reviews)
"Every staff member we encountered was very friendly. The property itself was clean but no frills. Continental breakfast was more than adequate. Would stay here again."
United States
Amy
$103 nightly
The price is $118
Jul 8 - Jul 9
Total with taxes and fees
Baldwin Inn & Suites, SureStay Collection by Best Western
Children's activities

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"The property is in terrible condition."
United States
Olga V
$66 nightly
The price is $72
Jul 22 - Jul 23
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
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, (181 reviews)
"It's a really nice place to stay!"
United States
Vidita
$129 nightly
The price is $144
Jul 8 - Jul 9
Total with taxes and fees
River Valley Inn
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (579 reviews)
"Such a peaceful and easy stay!"
United States
Mia
$110 nightly
The price is $122
Jul 22 - Jul 23
Total with taxes and fees
The Little Lion
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (874 reviews)
"I really enjoyed my stay at the Berkshire Inn, it was safe, clean, and in a convenient part of Pittsfield. Parking was a breeze and I was comfortable in my room. I would definitely book again!"
United States
Hannah
$83 nightly
The price is $92
Jul 13 - Jul 14
Total with taxes and fees
Berkshire Inn
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
9.0 out of 10, Wonderful, (446 reviews)
"He room was very clean, the staff was engaging and the breakfast was delicious. "
United States
John
$118 nightly
The price is $134
Jul 8 - Jul 9
Total with taxes and fees
Naomi's Inn Bed & Breakfast
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (420 reviews)
"Nice place for a stay"
United States
Jay
$110 nightly
The price is $123
Jul 13 - Jul 14
Total with taxes and fees
Sunset Inn
Lobby

Hampton Inn West Springfield

Hampton Inn West Springfield
2.5 star property
West Springfield
8.2 out of 10, Very Good, (1,007 reviews)
"Hotel was in a convenient location. However, very outdated."
United States
Faye
$106 nightly
The price is $121
Jul 12 - Jul 13
Total with taxes and fees
Hampton Inn West Springfield
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, (1,004 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
$127 nightly
The price is $142
Jul 8 - Jul 9
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (125 reviews)
"Breakfast was good, good location, friendly staff."
United States
Courtney
$152 nightly
The price is $170
Jul 16 - Jul 17
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,008 reviews)
"Clean room and breakfast"
United States
Raphael
$208 nightly
The price is $232
Jul 8 - Jul 9
Total with taxes and fees
The Red Lion Inn
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (881 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
$98 nightly
The price is $109
Jul 22 - Jul 23
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Terrace/patio

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2,127 reviews)
"Breakfast was excellent."
United States
Candyce
$142 nightly
The price is $158
Jul 12 - Jul 13
Total with taxes and fees
D. Hotel Suites & Spa
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,024 reviews)
"Spacious. Good coffee machine. Easy parking, check in and out."
United States
phyllis
$155 nightly
The price is $173
Aug 6 - Aug 7
Total with taxes and fees
Berkshire Mountain Lodge
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,005 reviews)
"Great lobby and dining room atmosphere!"
United States
Carin
$183 nightly
The price is $205
Jul 12 - Jul 13
Total with taxes and fees
Berkshires Untold
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.4 out of 10, Exceptional, (49 reviews)
"The East Rock Inn is great. It's comfortable, clean and close to downtown Great Barrington. This was my second time staying here."
United States
Laura
$164 nightly
The price is $184
Jul 22 - Jul 23
Total with taxes and fees
East Rock Inn
Lobby

Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield
2.5 star property
West Springfield
7.0 out of 10, Good, (1,011 reviews)
"Love the stay"
United States
Jake
$92 nightly
The price is $106
Jul 13 - Jul 14
Total with taxes and fees
Red Roof Inn PLUS+ West Springfield
Front of property

The Ellery

The Ellery
3.5 star property
Northampton
9.2 out of 10, Wonderful, (1,007 reviews)
"Amazing place to stay and fantastic location. Already wanting to plan my next trip!"
United States
Tara
$133 nightly
The price is $149
Aug 1 - Aug 2
Total with taxes and fees
The Ellery
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Had a lovely 2 night stay at the Red Lion Inn. The front desk staff were very welcoming. The location was convenient to many nice shops and restaurants, as well as sites like the Norman Rockwell museum and the Divine Mercies chapel and grounds. This hotel is a wonderful blend of historic and modern..and the breakfast is great!"
barbara 2-night trip
Posted 1 hour ago
The Red Lion Inn

Find out more about Chester

Chester Resorts information

Number of reviews
15,825
Accommodation
8 Resorts
Lowest Price
$69
Highest Price
$232

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 Becket Land Trust Historic Quarry and Littleville 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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