A snow-covered forest with a narrow stream running through it.

Best Resorts in Chester

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Check prices for these dates

Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6
In one month
Sep 18 - Sep 20
In two months
Oct 16 - Oct 18
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

Front of property

1. Becket Motel

Becket Motel
2.5 star property
Becket
6.6 out of 10, (63 reviews)
"Comfortable stay "
United States
Paul
$127 nightly
The price is $142
Sep 10 - Sep 11
Total with taxes and fees
Becket Motel
Lake view

2. Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.6 out of 10, Exceptional, (12 reviews)
"excellent lakeside view"
United States
mike
$141 nightly
The price is $158
Aug 31 - Sep 1
Total with taxes and fees
Berkshire Lake Lodge
Lobby

3. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,004 reviews)
"Very nice stay"
United States
Christine
$110 nightly
The price is $122
Sep 14 - Sep 15
Total with taxes and fees
Quality Inn Lee - Lenox South
Lobby

4. Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very Good, (900 reviews)
"The breakfast was delicious and the room was very nice and clean."
United States
Ace
$116 nightly
The price is $129
Sep 8 - Sep 9
Total with taxes and fees
Hampton Inn Westfield
Superior Room, 1 King Bed, Jetted Tub | Jetted tub

5. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,017 reviews)
"Very nice and convenient hotel."
United States
Karen
$158 nightly
The price is $176
Sep 14 - Sep 15
Total with taxes and fees
The Yankee Inn
Free daily buffet breakfast

6. Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (984 reviews)
"The rooms were very clean did not smell or anything"
United States
Christopher J.
$110 nightly
The price is $122
Sep 13 - Sep 14
Total with taxes and fees
Quality Inn Westfield - Springfield
Lake

7. 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, (1,009 reviews)
"enjoyable stay"
United States
James
$128 nightly
The price is $142
Sep 14 - Sep 15
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Seasonal outdoor pool

8. Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (435 reviews)
"It was a great stay, close to many amenities. The room was clean, with a comfortable bed."
Canada
Kevin
$108 nightly
The price is $121
Sep 1 - Sep 2
Total with taxes and fees
Sunset Inn
In-room dining

9. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (689 reviews)
"The outside of the hotel needed a lot of upkeep like paint and the stairs were particularly ugly. The inside was clean and neat and the people were wonderful. Great for a budget hotel."
United States
Lynne
$71 nightly
The price is $79
Sep 7 - Sep 8
Total with taxes and fees
Econo Lodge Lee - Great Barrington
Lobby

10. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,086 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
$125 nightly
The price is $139
Aug 31 - Sep 1
Total with taxes and fees
Berkshire Mountain Lodge
Property amenity

11. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
3.5 star property
South Lee
9.2 out of 10, Wonderful, (967 reviews)
"Always a great place to stay."
United States
Claudia
$135 nightly
The price is $150
Aug 31 - Sep 1
Total with taxes and fees
Holiday Inn Club Vacations Oak 'n Spruce Resort
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, desk, laptop workspace, blackout drapes

12. 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, (1,007 reviews)
"Quite comfortable Beds"
United States
Jermaine
$114 nightly
The price is $127
Sep 1 - Sep 2
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Front of property

13. The Ellery

The Ellery
3.5 star property
Northampton
9.2 out of 10, Wonderful, (1,020 reviews)
"Great stay."
United States
Holly
$149 nightly
The price is $166
Sep 9 - Sep 10
Total with taxes and fees
The Ellery
Outdoor spa tub

14. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
$355 nightly
The price is $397
Aug 25 - Aug 26
Total with taxes and fees
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

15. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (7 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$360 nightly
The price is $402
Sep 9 - Sep 10
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
In-room safe, desk, laptop workspace, iron/ironing board

16. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (901 reviews)
"Great hotel for a reasonable price. The only drawback is that they didn’t offer shampoos and body wash like most hotels but otherwise a great value."
United States
Sheila
$79 nightly
The price is $88
Aug 31 - Sep 1
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Lobby lounge

17. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,012 reviews)
"Nice Bar and cozy lobby. Enjoyed my stay."
United States
Pamela
$142 nightly
The price is $159
Sep 9 - Sep 10
Total with taxes and fees
Berkshires Untold
Property grounds

18. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,011 reviews)
"It is a little pricey for what you get but we loved the property and the area and will be back!"
United States
Patricia
$218 nightly
The price is $243
Sep 14 - Sep 15
Total with taxes and fees
The Red Lion Inn
Desk, iron/ironing board, WiFi (free), bed sheets

19. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (883 reviews)
"Well supplied in basics. Comfortable a/c. Downsides: having to call for service at the front door as no one is waiting at the desk, TV & or TV remote control didn’t work. Property needs renovating."
United States
Becky
$61 nightly
The price is $68
Aug 23 - Aug 24
Total with taxes and fees
FairBridge Inn Express
Indoor pool

20. 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, (170 reviews)
"A clean pleasant place to stay"
United States
Ken
$127 nightly
The price is $142
Sep 8 - Sep 9
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-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

FairBridge Inn Express

FairBridge Inn Express

10/10 Excellent
"It was very nice and everyone was extremely helpful"
ERICIA 1-night trip
Posted 8 hours ago
FairBridge Inn Express

Find out more about Chester

Chester Resorts information

Number of reviews
9,099
Accommodation
4 Resorts
Lowest Price
$68
Highest Price
$402

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 highest-rated resorts near Chester: Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA - 15 mi (24.1 km) from Chester. Has a fitness center. July 12-19 2026: Resort with 2 bedrooms and AC in the delightful Berkshires - 15.2 mi (24.4 km) from Chester. Amenities include a fitness center.
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 Glendale Falls.
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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