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Find hotels in Chester, MA from $70

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Check Chester hotel prices

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Jun 8 - Jun 9
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Jun 9 - Jun 10
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Jun 14 - Jun 16

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Compare 758 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior
The Black Swan Lee - Lenox, Ascend Hotel Collection
3.0 star property
9.0 out of 10, Wonderful, (1010)
"We are just stopping overnight, and feel we got lucky. This is a lovely small hotel on a lake with great views, boats to rent, and an excellent restaurant. It would be great for a vacation. "
The price is $127
$141 total
includes taxes & fees
Jun 16 - Jun 17
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Red Lion Inn
Outdoor pool, sun loungers
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (891)
"Always a great HISTORIC INN "
The price is $152
$193 total
includes taxes & fees
Jun 24 - Jun 25
The Red Lion Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
3.5 star property
9.0 out of 10, Wonderful, (479)
"."
The price is $149
$176 total
includes taxes & fees
Jun 11 - Jun 12
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
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Seven Hills Inn
Terrace/patio
Seven Hills Inn
4.0 star property
7.8 out of 10, Good, (467)
"Great breakfast, amazing property, comfortable beds! Water in shower wasn’t hot, had to take a “warm-cold” fast shower but it didn’t matter. The view, the quiet, nature and siting areas made the stay perfect. Will come again!!"
Seven Hills Inn
Lakehouse Inn
Aerial view
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (156)
"The experience was great and the staff were personable, helpful and warm."
The price is $136
$160 total
includes taxes & fees
Jun 10 - Jun 11
Lakehouse Inn
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Reception
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.4 out of 10, Exceptional, (651)
"I loved the staff and the accommodations. I’d recommend this property. "
The price is $188
$210 total
includes taxes & fees
Jun 12 - Jun 13
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
The Cornell Inn, Lenox
Porch
The Cornell Inn, Lenox
3.0 star property
8.8 out of 10, Excellent, (1002)
"The staff was very friendly and the breakfast was delicious. The outdoor areas were beautiful. The room was beautifully designed"
The price is $117
$137 total
includes taxes & fees
Jun 10 - Jun 11
The Cornell Inn, Lenox
Monument Mountain Motel
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel
2.5 star property
9.0 out of 10, Wonderful, (604)
"Cozy little room, very clean and comfortable, close to amenities, would definitely stay here again!"
The price is $95
$106 total
includes taxes & fees
Jun 16 - Jun 17
Monument Mountain Motel
Apple Tree Inn
Seasonal outdoor pool
Apple Tree Inn
3.0 star property
8.2 out of 10, Very Good, (215)
"The Appletree Inn newly aquired by Claire Collery, is a treasure! Claire, has taken every effort to make the Inn welcoming, elegant and comfortable for each guest who comes through their doors. The pool was clean and delightfully refreshing while looking out on the Berkshire Hills. The room in the lodge, was basic, but extremely clean and quiet. The main Inn had their "soft opening" of the bar last night, and it was just lovely, and a delicious breakfast with top notch Depot coffee awaited us...
The price is $179
$200 total
includes taxes & fees
Jun 17 - Jun 18
Apple Tree Inn
Quality Inn
Standard Room, 2 Queen Beds, Non Smoking | 1 bedroom, premium bedding, pillowtop beds, desk
Quality Inn
2.5 star property
8.2 out of 10, Very Good, (1011)
"Really clean and great staff"
The price is $104
$116 total
includes taxes & fees
Jun 16 - Jun 17
Quality Inn
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Standard Room | Premium bedding, pillowtop beds, in-room safe, desk
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, (504)
"Very nice place! Great pool and hot tub. A shower at the pool area would’ve been a nice addition to rinse off chlorine. Overall a great value for the money spent. "
The price is $131
$146 total
includes taxes & fees
Jun 17 - Jun 18
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Chambery Inn
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (356)
"Amazing place.."
The price is $249
$278 total
includes taxes & fees
Jun 10 - Jun 11
Chambery Inn
Blackberry River Inn
Library
Blackberry River Inn
3.0 star property
9.4 out of 10, Exceptional, (32)
"Great and excellent. Breakfast is perfect. "
The price is $182
$209 total
includes taxes & fees
Jun 17 - Jun 18
Blackberry River Inn
Travelodge by Wyndham Great Barrington Berkshires
In-room safe, desk, free cribs/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
7.6 out of 10, Good, (461)
"No amenities but that didn’t matter to us. Just needed a clean and quiet place for the night. I would stay here again"
The price is $75
$84 total
includes taxes & fees
Jun 16 - Jun 17
Travelodge by Wyndham Great Barrington Berkshires
The Briarcliff Motel
Exterior
The Briarcliff Motel
3.0 star property
8.8 out of 10, Excellent, (386)
"Great deal!"
The price is $114
$128 total
includes taxes & fees
Jun 10 - Jun 11
The Briarcliff Motel
The Ponds at Foxhollow by Capital Vacations
Property grounds
The Ponds at Foxhollow by Capital Vacations
3.0 star property
8.6 out of 10, Excellent, (110)
"Comfortable condo accommodations. Ample size, Workable kitchen. Comfortable bed. Lovely setting. And a community facility with a pool, workout equipment, and sauna too! Small but tangible complaint: outside lighting is very bright and shines into BR window. "
The Ponds at Foxhollow by Capital Vacations
Shaker Mill Inn
Garden
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (386)
"Wonderful place to stay in western Massachusetts."
The price is $227
$250 total
includes taxes & fees
Jun 10 - Jun 11
Shaker Mill Inn
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed | Desk, iron/ironing board, free cribs/infant beds, rollaway beds
Econo Lodge Lee - Great Barrington
2.0 star property
6.4 out of 10, (513)
"Good value"
The price is $70
$78 total
includes taxes & fees
Jun 11 - Jun 12
Econo Lodge Lee - Great Barrington
Locust Tree Bed and Breakfast LLC
Miscellaneous
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (326)
"Host was excellent and helpful. Location is quiet and close to nearby towns for activities. "
The price is $105
$121 total
includes taxes & fees
Jun 10 - Jun 11
Locust Tree Bed and Breakfast LLC
The Lenox Collection
Front of property
The Lenox Collection
3.5 star property
8.6 out of 10, Excellent, (214)
"This our second stay in this property. Our room was quite large and we had the lovely balcony overlooking the trees. The Constance is accessible to most of Lenox. The two recommendations would be to have some protein at breakfast, ie eggs, cheese instead of the foods that were laden with sugar and carbs. Also, the lobby noise at night was quite loud; We experienced the piano being played at 10:45pm. We had a hard time getting back to sleep."
The price is $98
$109 total
includes taxes & fees
Jun 16 - Jun 17
The Lenox Collection
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See all available properties in Chester
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.

More cheap stays in Chester

Quality Inn West Springfield

Quality Inn West Springfield

1150 Riverdale St, West Springfield, MA
The price is $80 per night from Jun 23 to Jun 24
$80
$90 total
includes taxes & fees
Jun 23 - Jun 24
7.2/10 Good! (1,017 reviews)

Stay near popular Chester attractions

Image for Chester Town Hall

Chester Town Hall

You can get tickets for a performance at Chester Town Hall during your trip to Chester. Wander the lakeside and forest in this relaxing area.

See properties
Chester Town Hall

Chester Travel Info

Number of reviews
5,896
Accommodation
758 hotels
Highest price
$249
Lowest price
$70
Why to go
Blandford Ski Area and Chester Town Hall

Frequently asked questions

What's the best place to stay in Chester?

D. Hotel Suites & Spa, located 19.1 mi (30.7 km) from the heart of Chester, is a top choice for your stay based on our traveler data. Other good choices for your trip to the area are La Quinta Inn & Suites by Wyndham Springfield MA and Red Roof Inn PLUS+ West Springfield. See all available top hotels, or vacation rentals in Chester.

What are some of the best vacation rentals in Chester?

Cozy apartment located in quiet Williamsburg: This vacation home rental outside of Chester is in a rural location and equipped with air-conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. See all vacation rentals in Chester.

If I need to cancel my hotel reservation in Chester, will I receive a refund?

Yes! Most hotel bookings are fully refundable as long as you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a non-refundable reservation, it may still be possible to cancel it and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

Where can I learn more about changing or cancelling my trip to Chester?

For additional details about picking new dates or cancelling your trip to Chester, go to https://www.expedia.com/service/.

What are some hotels with pools in Chester?

La Quinta Inn & Suites by Wyndham Springfield MA: 3-star hotel located near Springfield Museums. Offers a children's pool, an indoor pool, and a snack bar. Tru by Hilton Chicopee Springfield and D. Hotel Suites & Spa are two additional hotels that feature an onsite pool. View all hotels with pools in Chester.

What's the best accommodation near Logan International Airport (BOS)?

Hilton Boston Logan Airport is a popular 4-star hotel featuring a restaurant and an indoor pool. It's located a short 0.2 mi (0.4 km) from Logan Intl. Airport. Other accommodations close to the airport are Hyatt Regency Boston Harbor and Embassy Suites Boston Logan Airport.

What is staying in Chester like?

Visitors can enjoy all that Chester has to offer including the waterfalls, shopping, and riverfront. Tourists can also enjoy the city's restaurants, theaters, and monuments. In Chester, there are 2 hotels and other accommodations to choose from. Find out more about Chester.

What should I see while I'm in Chester?

A favorite place to visit is Chester Town Hall. You'll also find Jacob's Pillow and Otis Reservoir in the area. Check out what more to see and do in Expedia's Chester guide.

What's the seasonal 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.

Recent reviews of Chester hotels
Expedia verified reviews

The Ellery

The Ellery

5/5 Excellent
"Very friendly staff and I loved the breakfast and cookies"
A verified traveler stayed at The Ellery
Posted 1 day ago
The Ellery