Photo by Elizabeth Massa Peroulakis

Find hotels in Chester, MA from 2.196.756 ₫

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Tonight
3 Jul - 4 Jul
Tomorrow
4 Jul - 5 Jul
This weekend
4 Jul - 6 Jul
Next weekend
11 Jul - 13 Jul

Filter by

Guest rating
Guest rating
Property class

Top 10 Chester hotels and places to stay

The Constance by the Lenox Collection
Free WiFi, bed sheets

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (484)
"Had a fantastic stay, love this property. Cant wsit to go back"
The price is 4.784.349 ₫
5.344.117 ₫ total
includes taxes & fees
15 Jul - 16 Jul
The Constance by the Lenox Collection
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Nice place to stay. Good breakfast. "
The price is 4.209.191 ₫
4.701.667 ₫ total
includes taxes & fees
13 Jul - 14 Jul
The Yankee, Trademark Collection by Wyndham
The Black Swan Lee - Lenox, Ascend Hotel Collection
Lunch and dinner served, Indian cuisine

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Great place"
The price is 5.092.823 ₫
5.688.683 ₫ total
includes taxes & fees
13 Jul - 14 Jul
The Black Swan Lee - Lenox, Ascend Hotel Collection
Berkshires Untold
Lobby

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (621)
"Great place stay after an evening at Tanglewood!"
The price is 9.395.492 ₫
10.494.765 ₫ total
includes taxes & fees
5 Jul - 6 Jul
Berkshires Untold
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1000)
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
The price is 4.225.697 ₫
5.744.432 ₫ total
includes taxes & fees
14 Jul - 15 Jul
The Cornell Inn, Lenox & The Berkshires
Travelodge by Wyndham Great Barrington Berkshires
In-room safe, desk, free cots/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.6 out of 10, Good, (530)
"The staff was very friendly and the room was clean. "
The price is 2.590.236 ₫
2.893.215 ₫ total
includes taxes & fees
6 Jul - 7 Jul
Travelodge by Wyndham Great Barrington Berkshires
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed | Desk, iron/ironing board, free cots/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (604)
"Good location. Nice for an evening after a show at Tanglewood. "
The price is 1.670.314 ₫
1.865.741 ₫ total
includes taxes & fees
3 Aug - 4 Aug
Econo Lodge Lee - Great Barrington
Candlewood Suites West Springfield by IHG
Exterior

Candlewood Suites West Springfield by IHG

2.5 star property
8.4 out of 10, Very good, (725)
"A bit older facilities but otherwise meets all the basic needs and is easy on and off the 91 highway "
The price is 2.567.698 ₫
2.938.731 ₫ total
includes taxes & fees
13 Jul - 14 Jul
Candlewood Suites West Springfield by IHG
The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"I had excellent stay at the Red Lion Inn "
The price is 5.738.019 ₫
7.579.949 ₫ total
includes taxes & fees
4 Aug - 5 Aug
The Red Lion Inn
Red Roof Inn PLUS+ West Springfield
Lobby

Red Roof Inn PLUS+ West Springfield

2.5 star property
7.0 out of 10, Good, (1000)
"Rooms were clean and the staff was nice. "
The price is 2.448.950 ₫
2.802.823 ₫ total
includes taxes & fees
10 Jul - 11 Jul
Red Roof Inn PLUS+ West Springfield
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (808)
"Staff was welcoming and informative "
The price is 3.222.723 ₫
3.599.782 ₫ total
includes taxes & fees
13 Jul - 14 Jul
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1002)
"Great place to stay "
The price is 3.091.277 ₫
3.452.957 ₫ total
includes taxes & fees
13 Jul - 14 Jul
Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Standard Room | 1 bedroom, premium bedding, pillow-top beds, in-room safe

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (632)
"great place to stay"
The price is 4.343.224 ₫
4.851.381 ₫ total
includes taxes & fees
20 Jul - 21 Jul
Holiday Inn Express Hotel & Suites Great Barrington by IHG
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (733)
"Shampoo and toilet paper should have been In the room."
The price is 1.860.260 ₫
2.077.944 ₫ total
includes taxes & fees
17 Jul - 18 Jul
FairBridge Inn Express
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (367)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
Chambery Inn
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (558)
"The hotel is very clean, well-managed, and quiet, and it's conveniently located near Tanglewood and other attractions. The room is clean, and the staff are all extremely kind and attentive to our needs (special thanks to Tapan!) We will definitely be coming back!"
The price is 5.546.768 ₫
6.195.739 ₫ total
includes taxes & fees
15 Jul - 16 Jul
Courtyard by Marriott Lenox Berkshires
Quality Inn West Springfield
Seasonal outdoor pool

Quality Inn West Springfield

2.5 star property
7.0 out of 10, Good, (1000)
"Clean beds, great AC in room, good breakfast, pool was perfect. "
The price is 2.334.509 ₫
2.671.846 ₫ total
includes taxes & fees
13 Jul - 14 Jul
Quality Inn West Springfield
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (664)
"We love this place. It's a wonderful location in the Berkshires, easy to get to all of the surrounding towns and attractions. The amenities are awesome, the units are spotless, and the service is friendly and prompt. Have stayed twice and cannot wait to return again!"
The price is 4.131.191 ₫
4.979.790 ₫ total
includes taxes & fees
9 Jul - 10 Jul
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Hotel On North
Front of property – evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (742)
"Great boutique hotel"
The price is 4.944.996 ₫
5.523.482 ₫ total
includes taxes & fees
21 Jul - 22 Jul
Hotel On North
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Lobby

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (710)
"Nice outdoor seating areas, big pool, clean nicely appointed toom"
The price is 5.415.948 ₫
6.049.614 ₫ total
includes taxes & fees
9 Jul - 10 Jul
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Hotels with a spa in Chester may fit your trip

D. Hotel Suites & Spa
Indoor pool

D. Hotel Suites & Spa

3.0 star property
9.4 out of 10, Exceptional, (2282)
D. Hotel Suites & Spa
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.

Learn more about Chester

Experience the hiking, camping and monuments in Chester!

See all hotels in Chester
Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis

Frequently asked questions

What's the 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.