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10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
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31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

Motels in Chester

Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (803)
"Great place to stay for overnight stays. Breakfast was appreciated."
The price is AED 290
AED 324 total
includes taxes & fees
19 Oct - 20 Oct
Howard Johnson by Wyndham Lenox
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

2.5 star property
5.4 out of 10, (785)
"Good service and people"
The price is AED 294
AED 329 total
includes taxes & fees
16 Oct - 17 Oct
FairBridge Inn Express
Riverdale Inn
Exterior

Riverdale Inn

2.0 star property
6.0 out of 10, (999)
"How convenient the drive is and how everything is close by "
The price is AED 287
AED 328 total
includes taxes & fees
16 Oct - 17 Oct
Riverdale Inn
Berkshire Inn
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (822)
"The bed was very comfortable."
The price is AED 294
AED 328 total
includes taxes & fees
2 Nov - 3 Nov
Berkshire Inn
River Valley Inn
Basic Studio, 1 King Bed | Desk, laptop workspace, free WiFi, bed sheets

River Valley Inn

2.0 star property
8.6 out of 10, Excellent, (69)
"Great quiet motel. "
The price is AED 474
AED 529 total
includes taxes & fees
5 Oct - 6 Oct
River Valley Inn
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, (759)
"Good value for the price"
Monument Mountain Motel
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, (549)
"Excellent location, friendly service, clean, comfortable room."
The price is AED 275
AED 308 total
includes taxes & fees
5 Oct - 6 Oct
Travelodge by Wyndham Great Barrington Berkshires
The Little Lion
Exterior

The Little Lion

3.0 star property
8.6 out of 10, Excellent, (534)
"Comfy, quiet, and clean "
The price is AED 474
AED 529 total
includes taxes & fees
2 Nov - 3 Nov
The Little Lion
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, (635)
"Easy check in"
The price is AED 230
AED 257 total
includes taxes & fees
2 Nov - 3 Nov
Econo Lodge Lee - Great Barrington
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (628)
"Convenient location for my trip"
The price is AED 290
AED 324 total
includes taxes & fees
5 Oct - 6 Oct
Wagon Wheel Inn
Pleasant Valley Motel West Stockbridge
Exterior

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (1002)
"good average place to stay."
The price is AED 219
AED 240 total
includes taxes & fees
2 Nov - 3 Nov
Pleasant Valley Motel West Stockbridge
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (406)
"The staff is a one man operation,Which he is a very nice man,does a good job keeping up with the cleaning.Location is great walking distance to the town and plenty of restaurants."
The price is AED 367
AED 410 total
includes taxes & fees
6 Oct - 7 Oct
Sunset Inn
East Rock Inn
Premium Apartment | Private kitchen | Electric kettle

East Rock Inn

2.0 star property
9.4 out of 10, Exceptional, (32)
"Room was really comfortable and clean. Beautiful views from the main court yard during the day and at night the sky was full of stars. Amazing. "
The price is AED 473
AED 528 total
includes taxes & fees
2 Nov - 3 Nov
East Rock Inn
Becket Motel
Front of property

Becket Motel

2.5 star property
6.6 out of 10, (58)
"Comfortable stay "
The price is AED 349
AED 513 total
includes taxes & fees
5 Oct - 6 Oct
Becket Motel
Heart of the Berkshires
Economy Cabin | Premium bedding, individually decorated, free WiFi, bed sheets

Heart of the Berkshires

7.2 out of 10, Good, (9)
"Was great comfy quiet "
Heart of the Berkshires
Elm Motel
Reception

Elm Motel

2.0 star property
7.2 out of 10, Good, (123)
"Very clean, lacking bathroom and bathroom storage. Good price."
Elm Motel
Lantern House Motel
Gazebo

Lantern House Motel

2.5 star property
8.2 out of 10, Very Good, (455)
"The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should open the windows. How about I decide that? The room was musty-smelling, and everything was very dated and just didn't feel very clean. There are better options in Great Barrington. This is a place to...
Lantern House Motel
Red Carpet Inn West Springfield
Iron/ironing board, free WiFi

Red Carpet Inn West Springfield

2.0 star property
6.8 out of 10, (207)
"Did not like it bad experience"
Red Carpet Inn West Springfield
The Weathervane Motel
Property grounds

The Weathervane Motel

2.0 star property
7.2 out of 10, Good, (128)
"Booked a king bed but when I got there they told me no cable in that room. They gave me a room with a double bed that were on top of being small were very uncomfortable plus so much dust in air conditioner my allergies were affected plus it stunk couldn’t stay had to repack and go drive around and find a clean hotel plus staff never used a mask or gloves when I went back next day because I forgot my meds in drawer He told me he already cleaned room and there was nothing in the room I walked past...
The Weathervane Motel
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

La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent
"All that was needed is a Hot tub for these elderly bones and raise the temperature in the pool "
Frederick 1-night trip
Posted 22 hours ago
La Quinta Inn & Suites by Wyndham Springfield MA

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 827 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. Riverdale Inn is located 20.2 mi (32.5 km) from the heart of Chester. Enjoy access to the 24-hour front desk, and freebies including WiFi and parking. Howard Johnson by Wyndham Lenox: Free WiFi, free parking, and a 24-hour front desk are available during your stay. Central Chester is 17 mi (27.3 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. Berkshire Inn: Central Chester is 18.4 mi (29.6 km) away. A seasonal outdoor pool and free WiFi are available during your stay, along with room amenities like a microwave. FairBridge Inn Express: 17.4 mi (28 km) from the heart of Chester. Enjoy access to the business center, and freebies including WiFi and parking.
What can I do in Chester?
Some outdoorsy places nearby include Glendale Falls, Pyramid Lake, and Otis Reservoir. You'll find these family-friendly sights in the area: The Bookstore, Congregation Beth Israel, and Bousquet Ski Area. While you're checking out the area, consider visiting Chester Town Hall, Blandford Ski Area, 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.