Best Resorts in Chester

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Check prices for these dates

Next weekend
Jan 30 - Feb 1
In two weeks
Feb 6 - Feb 8
In one month
Feb 20 - Feb 22
In two months
Mar 20 - Mar 22
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

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, (1,005 reviews)
"Very friendly and good Breakfast."
United States
Jesse
$94 nightly
The price is $105
Jan 25 - Jan 26
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
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, (723 reviews)
"Always love staying here. The staff is fantastic, amenities are great, and the breakfast is just lovely. Will be returning soon!"
United States
Domenic
$107 nightly
The price is $120
Jan 25 - Jan 26
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (16 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
$139 nightly
The price is $155
Jan 27 - Jan 28
Total with taxes and fees
Element Lenox Berkshires
Indoor pool

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2,235 reviews)
"Great room and location."
United States
Karina
$114 nightly
The price is $128
Jan 22 - Jan 23
Total with taxes and fees
D. Hotel Suites & Spa
Lobby

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,005 reviews)
"Great Breakfast and parking! "
United States
Oluwatimilehin
$89 nightly
The price is $101
Jan 27 - Jan 28
Total with taxes and fees
Tru by Hilton Chicopee Springfield
Lobby

Hampton Inn West Springfield

Hampton Inn West Springfield
2.5 star property
West Springfield
8.2 out of 10, Very Good, (1,000 reviews)
"Very good place to stay"
United States
Gloria
$75 nightly
The price is $86
Feb 16 - Feb 17
Total with taxes and fees
Hampton Inn West Springfield
Front of property

The Ellery

The Ellery
3.5 star property
Northampton
9.2 out of 10, Wonderful, (946 reviews)
"The staff are wonderful and the it is always very clean!"
Canada
Mona
$115 nightly
The price is $128
Jan 26 - Jan 27
Total with taxes and fees
The Ellery
Exterior

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.4 out of 10, Very Good, (103 reviews)
"Clean room, comfortable bed, nice shower! Owners were very nice - we will definitely stay here again!"
United States
Deb
$99 nightly
The price is $111
Jan 21 - Jan 22
Total with taxes and fees
River Valley Inn
Exterior

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,007 reviews)
"The hotel is very nice and clean. From the moment we checked in to check out, we had an amazing time. "
United States
Gina
$93 nightly
The price is $103
Jan 28 - Jan 29
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
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
7.6 out of 10, Good, (109 reviews)
"Clean room and very spacious, staff was friendly, i would only add a small dinning table to the room. "
United States
Tomarie
$101 nightly
The price is $116
Jan 27 - Jan 28
Total with taxes and fees
Baldwin Inn & Suites, SureStay Collection by Best Western
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,001 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
$80 nightly
The price is $89
Feb 5 - Feb 6
Total with taxes and fees
Quality Inn Lee - Lenox South
Lobby

Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel
2.5 star property
West Springfield
9.4 out of 10, Exceptional, (129 reviews)
"Clean, cool rooms. Staff was very welcoming & professional."
United States
David
$119 nightly
The price is $136
Feb 11 - Feb 12
Total with taxes and fees
Blue – A Modern Hotel, an Ascend Collection Hotel
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, (1,006 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
$98 nightly
The price is $109
Jan 23 - Jan 24
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lake

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, (1,003 reviews)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
$101 nightly
The price is $113
Feb 1 - Feb 2
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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, (566 reviews)
"Excellent location!!"
United States
Abdul Samad
$75 nightly
The price is $84
Jan 21 - Jan 22
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (663 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
$128 nightly
The price is $143
Jan 23 - Jan 24
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
Lobby

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very Good, (822 reviews)
"I will stay again"
United States
Jailene
$126 nightly
The price is $141
Jan 30 - Jan 31
Total with taxes and fees
Hampton Inn Westfield
Restaurant

Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area
2.5 star property
Hadley
9.0 out of 10, Wonderful, (972 reviews)
"Best hotel in the area, hands down"
United States
alexander
$122 nightly
The price is $136
Feb 18 - Feb 19
Total with taxes and fees
Hampton Inn Hadley-Amherst Area
Room, 2 Queen Beds, 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, (818 reviews)
"Unbelieveably clean for the price."
United States
Micah
$67 nightly
The price is $74
Jan 21 - Jan 22
Total with taxes and fees
Monument Mountain Motel
Free daily buffet breakfast

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (910 reviews)
"Owner was very rude at check in"
United States
Robert
$94 nightly
The price is $104
Feb 8 - Feb 9
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

Find out more about Chester

Chester Resorts information

Number of reviews
16,010
Accommodation
4 Resorts
Lowest Price
$74
Highest Price
$155

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 Berkshire Scenic Railway Museum for some family fun. In the area, other attractions include Pyramid Lake and Kushi Institute.
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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