Chester Chalets

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    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

View from room

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
$120 nightly
The price is $134
Jun 1 - Jun 2
Total with taxes and fees
The Yankee Inn
Exterior

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, (1,001 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
$108 nightly
The price is $121
Jun 14 - Jun 15
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Exterior

Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western
2.5 star property
West Springfield
8.0 out of 10, Very Good, (193 reviews)
"Front desk staff was very friendly and informative. Great location for the local colleges."
United States
Chris
$108 nightly
The price is $124
Jun 10 - Jun 11
Total with taxes and fees
Baldwin Inn & Suites, SureStay Collection by Best Western
Exterior

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (857 reviews)
"This is a great choice for folks traveling on a budget. Clean rooms, friendly owners, and nice retro vibe. Will be staying here again on my trips through the Berkshires."
United States
Mark
$86 nightly
The price is $96
Jun 2 - Jun 3
Total with taxes and fees
Monument Mountain Motel
Exterior

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)
"It was a clean, friendly hotel."
United States
Cheri
$113 nightly
The price is $126
Jun 2 - Jun 3
Total with taxes and fees
Quality Inn Lee - Lenox South
Front of property

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2,189 reviews)
"Spacious room, very helpful staff, good coffee and an excellent breakfast."
United States
Clifford
$109 nightly
The price is $122
Jun 2 - Jun 3
Total with taxes and fees
D. Hotel Suites & Spa
Property entrance

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (960 reviews)
"Great location and resort. Very happy with accommodation's"
United States
Robert
$155 nightly
The price is $173
Jun 1 - Jun 2
Total with taxes and fees
Berkshire Mountain Lodge
Exterior

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, (99 reviews)
"This is a great hotel-super clean, nice breakfast, staff very pleasant and helpful. Close to Pittsfield but quieter. Pool and hot tub were great. Highly recommend staying here if you’re in the area."
United States
Kathleen
$135 nightly
The price is $151
Jun 4 - Jun 5
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Exterior

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.6 out of 10, Excellent, (159 reviews)
"Friendly staff, great under the radar spot alternative to chain motels!"
United States
Anthony
$116 nightly
The price is $130
Jun 7 - Jun 8
Total with taxes and fees
River Valley Inn
Children's activities

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"The property is in terrible condition."
United States
Olga V
$70 nightly
The price is $77
Jun 14 - Jun 15
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
Exterior

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,004 reviews)
"It was a great stay."
United States
Geovani
$115 nightly
The price is $131
Jun 22 - Jun 23
Total with taxes and fees
Tru by Hilton Chicopee Springfield
Exterior

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (964 reviews)
"Friendly good location"
United States
Vivian
$119 nightly
The price is $133
Jun 1 - Jun 2
Total with taxes and fees
Berkshires Untold
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, (861 reviews)
"very friendly, room was nice and breakfast was great"
United States
Lawrence
$122 nightly
The price is $136
Jun 28 - Jun 29
Total with taxes and fees
Hampton Inn Westfield
Exterior

TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
3.0 star property
Hadley
9.6 out of 10, Exceptional, (88 reviews)
"Friendly staff, clean room, awesome breakfast"
United States
Matthew
$180 nightly
The price is $201
Jun 14 - Jun 15
Total with taxes and fees
TownePlace Suites by Marriott Hadley Amherst
Exterior

Hampton Inn West Springfield

Hampton Inn West Springfield
2.5 star property
West Springfield
8.2 out of 10, Very Good, (1,002 reviews)
"Our room was very clean, staff was very friendly. We would stay here again."
United States
Sherry
$89 nightly
The price is $101
Jun 9 - Jun 10
Total with taxes and fees
Hampton Inn West Springfield
Porch

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (442 reviews)
"He room was very clean, the staff was engaging and the breakfast was delicious. "
United States
John
$118 nightly
The price is $134
Jun 3 - Jun 4
Total with taxes and fees
Naomi's Inn Bed & Breakfast
Exterior

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (580 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
$79 nightly
The price is $88
Jun 1 - Jun 2
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
Exterior

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (933 reviews)
"Very clean& maintained. Most comfortable bed I've slept in"
United States
Keith
$100 nightly
The price is $112
Jun 21 - Jun 22
Total with taxes and fees
Quality Inn Westfield - Springfield
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,001 reviews)
"a delightful inn centrally located in charming Stockbridge"
United States
molly
$197 nightly
The price is $220
Jun 9 - Jun 10
Total with taxes and fees
The Red Lion Inn
Front of property

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (562 reviews)
"Such a peaceful and easy stay!"
United States
Mia
$110 nightly
The price is $123
Jun 1 - Jun 2
Total with taxes and fees
The Little Lion
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

Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western

2/10 Terrible
"First off the dishwasher was full of dirty dishes and it smelled they had glass cups in the drawer with the silverware just all thrown in one drawer the air conditioner sucked I had to clean the lint out of it to work properly and on the memorial weekend the had no supplies the breakfast was not enough they had no drinks for children other than coffee and hot chocolate and when I asked about it one of the staff that wasn't working that day but showed up to eat for free chimed in to say that they can have hot chocolate I just rolled my eyes and walked away she decided to tell the staff that was working that if she was working she would have punched me in the fn face my son was there and I was disgusted with the whole stay I tried calling management but the female keeps answering the phone and tells me every day that he isn't in maybe tomorrow"
Christine 2-night trip
Posted 1 hour ago
Baldwin Inn & Suites, SureStay Collection by Best Western

Find out more about Chester

Chester Chalets information

Number of reviews
15,898
Accommodation
3 Chalets
Lowest Price
$77
Highest Price
$220

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