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Check prices for these dates

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28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec
In one month
19 Dec - 21 Dec
In two months
16 Jan - 18 Jan

Resorts in Chester

No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

Lobby sitting area
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, (1000)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is AED 240
AED 268 total
includes taxes & fees
24 Nov - 25 Nov
Best Western Plus Berkshire Hills Inn & Suites
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (962)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is AED 324
AED 362 total
includes taxes & fees
21 Nov - 22 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lobby
Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel

2.5 star property
West Springfield
9.6 out of 10, Exceptional, (92)
"Great staff super nice beautiful hotel lots of parking "
United States
Yovelys
The price is AED 395
AED 452 total
includes taxes & fees
10 Dec - 11 Dec
Blue – A Modern Hotel, an Ascend Collection Hotel
Reception
Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western

2.5 star property
West Springfield
7.6 out of 10, Good, (99)
"Clean room, friendly staff, good mattress. Not fancy or plush, but perfect for a one or two night place to land while attending events at the Big E. "
United States
Kim
The price is AED 372
AED 426 total
includes taxes & fees
26 Nov - 27 Nov
Baldwin Inn & Suites, SureStay Collection by Best Western
Lobby
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

2.5 star property
Chicopee
8.8 out of 10, Excellent, (1000)
"Nice place and clean i recommend it. "
Mexico
Jessly
The price is AED 320
AED 363 total
includes taxes & fees
3 Dec - 4 Dec
Tru by Hilton Chicopee Springfield
Room, 1 Queen Bed, 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, (791)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1005)
"Great stay!"
United States
Ann
The price is AED 282
AED 315 total
includes taxes & fees
2 Dec - 3 Dec
The Yankee, Trademark Collection by Wyndham
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, (811)
"Good staff, clean, convenient"
United States
Harlan
The price is AED 391
AED 437 total
includes taxes & fees
10 Dec - 11 Dec
Hampton Inn Westfield
Exterior
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, (695)
"Everything was wonderful....super clean rooms, check-in was fast and smooth, staff was on top of everything. We definitely will be back at Holiday Inn. "
United States
Tabitha
The price is AED 393
AED 439 total
includes taxes & fees
25 Nov - 26 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Indoor pool
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2251)
"Very clean room, great variety of food at breakfast, friendly and helpful staff."
United States
Liz
The price is AED 404
AED 469 total
includes taxes & fees
23 Nov - 24 Nov
D. Hotel Suites & Spa
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, (559)
"The staff were very friendly and accommodating "
United States
Tom
The price is AED 275
AED 308 total
includes taxes & fees
23 Nov - 24 Nov
Travelodge by Wyndham Great Barrington Berkshires
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (824)
"Staff was very friendly and helpful."
United States
Pamela
The price is AED 290
AED 324 total
includes taxes & fees
20 Nov - 21 Nov
Howard Johnson by Wyndham Lenox
Exterior
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, (1000)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is AED 403
AED 450 total
includes taxes & fees
9 Dec - 10 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is AED 496
AED 554 total
includes taxes & fees
4 Dec - 5 Dec
Element Lenox Berkshires
Exterior
Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area

2.5 star property
Hadley
9.0 out of 10, Wonderful, (953)
"Nice hotel, friendly helpful staff"
United States
Tim
The price is AED 438
AED 489 total
includes taxes & fees
11 Dec - 12 Dec
Hampton Inn Hadley-Amherst Area
Basic Studio, 1 King Bed | 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, (97)
"Clean room, comfortable bed, nice shower! Owners were very nice - we will definitely stay here again!"
United States
Deb
The price is AED 400
AED 447 total
includes taxes & fees
20 Nov - 21 Nov
River Valley Inn
Exterior
Candlewood Suites West Springfield by IHG

Candlewood Suites West Springfield by IHG

2.5 star property
West Springfield
8.4 out of 10, Very Good, (785)
"Nice, friendly staff, clean room and comfortable suite.. highly recommend "
United States
Christopher
The price is AED 360
AED 412 total
includes taxes & fees
24 Nov - 25 Nov
Candlewood Suites West Springfield by IHG
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (759)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
Seasonal outdoor pool
Sunset Inn

Sunset Inn

2.0 star property
Lee
7.6 out of 10, Good, (410)
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
The price is AED 314
AED 351 total
includes taxes & fees
3 Dec - 4 Dec
Sunset Inn
Lobby sitting area
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, (60)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is AED 387
AED 432 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"Clean, cozy, workers are very attentive. The bar and activity center is a lot of fun. "
Paige 2-night trip
Posted 2 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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 Littleville Lake 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.