Search Motels in Chester from CA $91

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Check prices for these dates

Next weekend
May 29 - May 31
In two weeks
Jun 5 - Jun 7
In one month
Jun 19 - Jun 21
In two months
Jul 17 - Jul 19

Our top choices for Chester motels

Room, 2 Queen Beds, Non Smoking

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (855 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is CA $94
CA $105 total
includes taxes & fees
May 25 - May 26
Monument Mountain Motel
Studio Suite, Multiple Beds

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.6 out of 10, Excellent, (152 reviews)
"Welcome Bag and great restaurant recommendations. Enjoyed our stay. "
United States
Ashlyn Jane
The price is CA $159
CA $177 total
includes taxes & fees
Jun 1 - Jun 2
River Valley Inn
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, (579 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 $103
CA $115 total
includes taxes & fees
May 19 - May 20
Travelodge by Wyndham Great Barrington Berkshires
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, (853 reviews)
"Great value"
United States
Ralph
The price is CA $109
CA $121 total
includes taxes & fees
May 19 - May 20
Howard Johnson by Wyndham Lenox
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (561 reviews)
"Avoid this place."
United States
Carole
The price is CA $131
CA $146 total
includes taxes & fees
Jun 11 - Jun 12
The Little Lion
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, (44 reviews)
"The East Rock Inn is great. It's comfortable, clean and close to downtown Great Barrington. This was my second time staying here."
United States
Laura
The price is CA $188
CA $211 total
includes taxes & fees
Jun 2 - Jun 3
East Rock Inn
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (855 reviews)
"Clean comfortable room. Very nice staff. Close to everything in downtown Pittsfield. This is the only place I stay when I’m in Pittsfield. Very peaceful. Excellent place to relax. "
United States
Jennifer
The price is CA $110
CA $123 total
includes taxes & fees
May 20 - May 21
Berkshire Inn
Desk, laptop workspace, blackout drapes, iron/ironing board

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,002 reviews)
"The property is in terrible condition."
United States
Olga V
The price is CA $83
CA $91 total
includes taxes & fees
May 30 - May 31
Pleasant Valley Motel West Stockbridge
Lobby

Elm Motel

Elm Motel
2.0 star property
Westfield
7.2 out of 10, Good, (123 reviews)
"Jeannie at the front desk was helpful and very welcoming. Room was renovated since my last visit. "
United States
WAYNE
The price is CA $122
CA $137 total
includes taxes & fees
May 24 - May 25
Elm Motel
Room amenity

Riverdale Inn

Riverdale Inn
2.0 star property
West Springfield
6.0 out of 10, (1,004 reviews)
"Get breakfast available"
United States
Jesse
The price is CA $106
CA $122 total
includes taxes & fees
May 20 - May 21
Riverdale Inn
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (413 reviews)
"Nice place for a stay"
United States
Jay
The price is CA $145
CA $162 total
includes taxes & fees
Jun 1 - Jun 2
Sunset Inn
In-room dining

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (663 reviews)
"Good to stay. "
United States
Ibinabo
The price is CA $103
CA $115 total
includes taxes & fees
May 19 - May 20
Econo Lodge Lee - Great Barrington
Front of property

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (60 reviews)
"Comfortable stay "
United States
Paul
The price is CA $131
CA $192 total
includes taxes & fees
Jun 2 - Jun 3
Becket Motel
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (819 reviews)
"Scammers!! I booked a night just to shower and refresh. An abandoned public bathroom is 100 times cleaner than their room"
United States
Elie
The price is CA $98
CA $109 total
includes taxes & fees
May 19 - May 20
FairBridge Inn Express
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

Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

4/10 Poor
"The room had a very STRONG unpleasant smell and was told couldn't change rooms because they were completely booked and I booked through a 3rd party. I asked for some kind of disinfectant or smell spray, never received. I had to buy my own and use my expensive parfume to mask the smell. I was up all night coughing from the smell, had to put vicks vapor rub in my noise.I asked for a discount and was told it will go on a card/ not fully funded so that i can go elsewhere but everywhere i looked was booked. I also asked for an iron/ ironing board and was told only certain rooms have them. The bathroom door knob on both sides were broken and a dent in the door, my hubby noticed what looked like slashes from a knife in curtains. I will NEVER stay here again I dont care how reasonable the price is or if they gave me a room for free and I stayed in all types of hotels that are low budget."
Christina 2-night trip
Posted 2 hours ago
Red Roof Inn PLUS+ West Springfield

Find out more about Chester

Chester Motels information

Number of reviews
6,405
Accommodation
19 Motels
Lowest Price
CA $91
Highest Price
CA $211

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 871 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. River Valley Inn is located 18.6 mi (29.9 km) from the heart of Chester. Enjoy access to the 24-hour front desk, 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. Monument Mountain Motel: Enjoy access to the picnic area, and freebies including WiFi and parking. Located 19.5 mi (31.4 km) from the heart of Chester. The Little Lion: Central Chester is 18.4 mi (29.6 km) away. Free WiFi and free parking are available during your stay, along with room amenities like a microwave. Howard Johnson by Wyndham Lenox: 17 mi (27.3 km) from the heart of Chester. Enjoy access to the 24-hour front desk, 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: Berkshire Scenic Railway Museum, The Bookstore, and Congregation Beth Israel. While you're checking out the area, consider visiting Chester Town Hall, Pyramid Lake, and Jacob's Pillow.
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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