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Search Motels in Chester from CA $97

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Check prices for these dates

Next weekend
Jul 24 - Jul 26
In two weeks
Jul 31 - Aug 2
In one month
Aug 14 - Aug 16
In two months
Sep 11 - Sep 13

Our top choices for Chester motels

Studio Suite, Multiple Beds

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.6 out of 10, Excellent, (187 reviews)
"It's a really nice place to stay!"
United States
Vidita
The price is CA $149
CA $167 total
includes taxes & fees
Aug 12 - Aug 13
River Valley Inn
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (855 reviews)
"Some of the furniture and rugs show age. The bed was comfortable and the staff was always available to help!"
United States
DAVID
The price is CA $87
CA $97 total
includes taxes & fees
Aug 13 - Aug 14
FairBridge Inn Express
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (425 reviews)
"It was a great stay, close to many amenities. The room was clean, with a comfortable bed."
Canada
Kevin
The price is CA $125
CA $140 total
includes taxes & fees
Jul 22 - Jul 23
Sunset 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, (1,000 reviews)
"Very comfortable. Will stay there again"
United States
Peter
The price is CA $95
CA $104 total
includes taxes & fees
Jul 19 - Jul 20
Pleasant Valley Motel West Stockbridge
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (885 reviews)
"Great place"
United States
Luciane
The price is CA $139
CA $155 total
includes taxes & fees
Jul 19 - Jul 20
Howard Johnson by Wyndham Lenox
Room, 2 Queen Beds, Non Smoking

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (881 reviews)
"I was pleasantly surprised how clean,spacious,quiet and comfortable the room was ( two queens) Loved the place."
United States
Yekaterina
The price is CA $156
CA $174 total
includes taxes & fees
Jul 30 - Jul 31
Monument Mountain Motel
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (880 reviews)
"Clean, quiet, friendly, no frills but everything needed. Mattresses were very good."
United States
James
The price is CA $126
CA $141 total
includes taxes & fees
Jul 20 - Jul 21
Berkshire Inn
Lake view

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.4 out of 10, Exceptional, (6 reviews)
"Everything was perfect!!"
United States
Grzegorz
The price is CA $286
CA $319 total
includes taxes & fees
Jul 19 - Jul 20
Berkshire Lake Lodge
Room amenity

Riverdale Inn

Riverdale Inn
2.0 star property
West Springfield
6.0 out of 10, (999 reviews)
"Grwat"
United States
Israel
The price is CA $106
CA $121 total
includes taxes & fees
Jul 18 - Jul 19
Riverdale Inn
In-room safe, desk, cribs (free), rollaway beds (free)

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.4 out of 10, Good, (593 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
The price is CA $139
CA $155 total
includes taxes & fees
Aug 2 - Aug 3
Travelodge by Wyndham Great Barrington Berkshires
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.4 out of 10, Exceptional, (50 reviews)
"Virtual check in. I prefer real staff."
United States
Eleanor
The price is CA $238
CA $265 total
includes taxes & fees
Aug 3 - Aug 4
East Rock Inn
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (583 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is CA $177
CA $198 total
includes taxes & fees
Aug 9 - Aug 10
The Little Lion
Front of property

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (61 reviews)
"Comfortable stay "
United States
Paul
The price is CA $148
CA $213 total
includes taxes & fees
Jul 20 - Jul 21
Becket Motel
In-room dining

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (676 reviews)
"Good location to towns in area"
United States
William
The price is CA $118
CA $132 total
includes taxes & fees
Aug 11 - Aug 12
Econo Lodge Lee - Great Barrington
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"The staff were very friendly and helpful. It’s a rustic style hotel room but having the full kitchen was amazing! Great location and cozy room."
Jamie 2-night trip
Posted 11 hours ago
Berkshire Mountain Lodge

Find out more about Chester

Chester Motels information

Number of reviews
7,405
Accommodation
19 Motels
Lowest Price
CA $97
Highest Price
CA $319

Frequently asked questions

What can I expect from a motel trip to Chester?
If you're having a hard time finding motels in Chester, let Expedia help you find a motel or something similar from over 875 lodging options in the larger area. Just use our search tools to filter by price per night or cost-saving amenities such as free parking and free airport transportation.
What is a motel?
When you stay at a motel, you'll often find an outdoor pool and free parking. With a stay at a motel, you'll usually access your room directly from the parking lot. Starting in the early 1950s, customized neon signs often lit up the roadside motels, and you can see these today along the historic U.S. Route 66.
What are the best motels in Chester?
These are some of our customers' favorite motels to book in the larger area. FairBridge Inn Express is located 17.4 mi (28 km) from the heart of Chester. Enjoy access to the business center, and freebies including WiFi and parking. Riverdale Inn: Free WiFi and free parking are available during your stay, along with room amenities like air conditioning. Central Chester is 20.2 mi (32.5 km) away. River Valley Inn: Enjoy access to the 24-hour front desk, and freebies including WiFi and parking. Located 18.6 mi (29.9 km) from the heart of Chester. Howard Johnson by Wyndham Lenox: Central Chester is 17 mi (27.3 km) away. Free parking and a 24-hour front desk are available during your stay, along with room amenities like a soaking tub. The Little Lion: 18.4 mi (29.6 km) from the heart of Chester. Enjoy access to the picnic area, and freebies including WiFi and parking.
What can I do in Chester?
Some outdoorsy places nearby include Littleville Lake, Glendale Falls, and Iroquis Waterfront. You'll find these family-friendly sights in the area: Bousquet Ski Area, Berkshire Museum, and Land of Providence. While you're checking out the area, consider visiting Chester Town Hall, Pyramid Lake, and Skyline Trail.
What's the weather like in Chester?
Weather can make or break a roadtrip, so here's some data about year-round temperatures in Chester to help you plan yours: 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 are my options for getting around Chester when staying in a motel?
We've gathered some information about getting around Chester to help you navigate your stay: Fly into Westfield, MA (BAF-Barnes Municipal), which is located 15.4 mi (24.7 km) from the city center. Otherwise, look for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 18.9 mi (30.4 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

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