Photo by Elizabeth Massa Peroulakis

Best Resorts in Chester

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Dec 19 - Dec 21
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Jan 16 - Jan 18

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
$93 nightly
The price is $104
Nov 23 - Nov 24
Total with taxes and fees
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
$88 nightly
The price is $99
Nov 22 - Nov 23
Total with taxes and fees
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, (1000)
"Nice place and clean i recommend it. "
Mexico
Jessly
$87 nightly
The price is $99
Dec 1 - Dec 2
Total with taxes and fees
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
$110 nightly
The price is $125
Dec 10 - Dec 11
Total with taxes and fees
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
$101 nightly
The price is $116
Nov 26 - Nov 27
Total with taxes and fees
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
$107 nightly
The price is $120
Nov 25 - Nov 26
Total with taxes and fees
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
$77 nightly
The price is $86
Dec 7 - Dec 8
Total with taxes and fees
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)
"Very pet friendly and the night check in agent was super kind and friendly"
United States
olivia townsend
$107 nightly
The price is $120
Dec 10 - Dec 11
Total with taxes and fees
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
$79 nightly
The price is $88
Nov 20 - Nov 21
Total with taxes and fees
Howard Johnson by Wyndham Lenox
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
$75 nightly
The price is $84
Nov 21 - Nov 22
Total with taxes and fees
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
$135 nightly
The price is $151
Nov 30 - Dec 1
Total with taxes and fees
Element Lenox Berkshires
Lobby
Quality Inn

Quality Inn

2.5 star property
Lee
8.4 out of 10, Very Good, (1001)
"Clean room and good breakfast "
United States
Kelly
$93 nightly
The price is $104
Dec 7 - Dec 8
Total with taxes and fees
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
$119 nightly
The price is $133
Dec 11 - Dec 12
Total with taxes and fees
Hampton Inn Hadley-Amherst Area
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.
$67 nightly
The price is $74
Nov 20 - Nov 21
Total with taxes and fees
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
$110 nightly
The price is $122
Dec 10 - Dec 11
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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
$109 nightly
The price is $122
Nov 20 - Nov 21
Total with taxes and fees
River Valley Inn
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
$134 nightly
The price is $150
Nov 23 - Nov 24
Total with taxes and fees
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
$76 nightly
The price is $85
Dec 5 - Dec 6
Total with taxes and fees
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
$118 nightly
The price is $135
Nov 23 - Nov 24
Total with taxes and fees
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
$98 nightly
The price is $109
Dec 3 - Dec 4
Total with taxes and fees
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.
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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

Find out more about Chester

Chester Resorts information

Number of reviews
15,000
Accommodation
5 Resorts
Lowest Price
$74
Highest Price
$151

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.

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