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Search Resorts in Chester

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Check prices for these dates

Next weekend
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
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, (1001)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is HK$728
HK$813 total
includes taxes & fees
23 Nov - 24 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 HK$695
HK$777 total
includes taxes & fees
29 Nov - 30 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lobby
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

2.5 star property
Chicopee
8.8 out of 10, Excellent, (1001)
"Nice place and clean i recommend it. "
Mexico
Jessly
The price is HK$679
HK$770 total
includes taxes & fees
3 Dec - 4 Dec
Tru by Hilton Chicopee Springfield
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 HK$822
HK$941 total
includes taxes & fees
7 Dec - 8 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, (100)
"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 HK$789
HK$903 total
includes taxes & fees
8 Dec - 9 Dec
Baldwin Inn & Suites, SureStay Collection by Best Western
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 HK$833
HK$931 total
includes taxes & fees
24 Nov - 25 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 HK$598
HK$668 total
includes taxes & fees
4 Dec - 5 Dec
The Yankee, Trademark Collection by Wyndham
Premium bedding, desk, laptop workspace, blackout curtains
Hampton Inn Westfield

Hampton Inn Westfield

2.5 star property
Westfield
8.4 out of 10, Very good, (813)
"Very pet friendly and the night check in agent was super kind and friendly"
United States
olivia townsend
The price is HK$816
HK$912 total
includes taxes & fees
10 Dec - 11 Dec
Hampton Inn Westfield
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 HK$615
HK$687 total
includes taxes & fees
8 Dec - 9 Dec
Howard Johnson by Wyndham Lenox
In-room safe, desk, free cots/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 HK$584
HK$652 total
includes taxes & fees
17 Dec - 18 Dec
Travelodge by Wyndham Great Barrington Berkshires
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 HK$1,020
HK$1,139 total
includes taxes & fees
11 Dec - 12 Dec
Element Lenox Berkshires
Lobby
Quality Inn

Quality Inn

2.5 star property
Lee
8.4 out of 10, Very good, (1002)
"Clean room and good breakfast "
United States
Kelly
The price is HK$721
HK$806 total
includes taxes & fees
7 Dec - 8 Dec
Quality Inn
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 HK$928
HK$1,036 total
includes taxes & fees
11 Dec - 12 Dec
Hampton Inn Hadley-Amherst Area
Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (792)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
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 HK$827
HK$924 total
includes taxes & fees
11 Dec - 12 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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 HK$848
HK$948 total
includes taxes & fees
14 Dec - 15 Dec
River Valley Inn
Indoor pool
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2254)
"Very clean room, great variety of food at breakfast, friendly and helpful staff."
United States
Liz
The price is HK$665
HK$773 total
includes taxes & fees
14 Dec - 15 Dec
D. Hotel Suites & Spa
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 HK$666
HK$744 total
includes taxes & fees
2 Dec - 3 Dec
Sunset Inn
View from property
Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield

3.0 star property
West Springfield
9.2 out of 10, Wonderful, (567)
"Room was clean and staff was super friendly "
United States
Jessuca
The price is HK$920
HK$1,053 total
includes taxes & fees
23 Nov - 24 Nov
Courtyard by Marriott West Springfield
Lobby
Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield

2.5 star property
Westfield
7.2 out of 10, Good, (896)
"Staff was very friendly. Everything was clean and well kept. Small hotel but very cozy and quiet."
United States
Gloria
The price is HK$728
HK$813 total
includes taxes & fees
21 Dec - 22 Dec
Quality Inn Westfield - Springfield
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.
View all properties

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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
"Every thing about the resort is excellent!"
Siobhan 7-night trip
Posted 2 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Find out more about Chester

Chester Resorts information

Number of reviews
14,994
Accommodation
4 Resorts
Lowest Price
HK$652
Highest Price
HK$1,139

Frequently asked questions

What is Chester like for a resort holiday?
You deserve a holiday, and a resort is the perfect place to find all the amenities and services you need for a relaxing time in Chester. One of the comfortable resorts in the area might be just what you're looking for, whether you're hoping for an amazing pool, a state-of-the-art fitness centre or fun activities to try.
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. Has a sauna, a fitness centre and a terrace.
What can I do in Chester?
Experience the local theatre scene at Chester Town Hall, or take the kids to Ashintully Gardens for some family fun. In the area, other attractions include Littleville Lake and Pyramid Lake.
What's the seasonal weather like in Chester?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Chester are January, February, November and March, with each month seeing an average of 15 cm 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) away from the heart of the city. Otherwise, look 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, consider renting a car to explore more sights.

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