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Check prices for these dates

Next weekend
30 Jan - 1 Feb
In two weeks
6 Feb - 8 Feb
In one month
20 Feb - 22 Feb
In two months
20 Mar - 22 Mar

Our top choices for Chester motels

Exterior

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.4 out of 10, Very Good, (103 reviews)
"Clean room, comfortable bed, nice shower! Owners were very nice - we will definitely stay here again!"
United States
Deb
The price is SAR 371
SAR 415 total
includes taxes & fees
1 Feb - 2 Feb
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, (566 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is SAR 281
SAR 314 total
includes taxes & fees
25 Jan - 26 Jan
Travelodge by Wyndham Great Barrington Berkshires
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (818 reviews)
"Unbelieveably clean for the price."
United States
Micah
Monument Mountain Motel
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, (829 reviews)
"Staff was very friendly and helpful."
United States
Pamela
The price is SAR 296
SAR 331 total
includes taxes & fees
30 Jan - 31 Jan
Howard Johnson by Wyndham Lenox
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (841 reviews)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is SAR 306
SAR 342 total
includes taxes & fees
25 Jan - 26 Jan
Berkshire Inn
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (549 reviews)
"Perfect for pets "
United States
Maria
The price is SAR 412
SAR 461 total
includes taxes & fees
25 Jan - 26 Jan
The Little Lion
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (37 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is SAR 491
SAR 548 total
includes taxes & fees
25 Jan - 26 Jan
East Rock 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, (1,001 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is SAR 219
SAR 241 total
includes taxes & fees
22 Jan - 23 Jan
Pleasant Valley Motel West Stockbridge
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (411 reviews)
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
The price is SAR 356
SAR 398 total
includes taxes & fees
24 Jan - 25 Jan
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, (654 reviews)
"The room was clean and the service adequate"
United States
David
The price is SAR 253
SAR 283 total
includes taxes & fees
27 Jan - 28 Jan
Econo Lodge Lee - Great Barrington
Lobby

Elm Motel

Elm Motel
2.0 star property
Westfield
7.2 out of 10, Good, (123 reviews)
"Very clean, lacking bathroom and bathroom storage. Good price."
United States
Daniel
The price is SAR 334
SAR 373 total
includes taxes & fees
22 Jan - 23 Jan
Elm Motel
Room amenity

Riverdale Inn

Riverdale Inn
2.0 star property
West Springfield
5.8 out of 10, (1,001 reviews)
"Great people and wonderful room!!"
United States
Jeffrey
The price is SAR 256
SAR 293 total
includes taxes & fees
17 Feb - 18 Feb
Riverdale 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, (811 reviews)
"Room spotless and staff helpful."
United States
William
The price is SAR 300
SAR 336 total
includes taxes & fees
4 Feb - 5 Feb
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Best, kindest, most capable and courteous staff I’ve encountered in a long while. "
Matthew 1-night trip
Posted 1 day ago
The Yankee, Trademark Collection by Wyndham

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 834 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. The Little Lion: Free WiFi and free parking are available during your stay, along with room amenities like air conditioning. Central Chester is 18.4 mi (29.6 km) away. Howard Johnson by Wyndham Lenox: Enjoy access to the 24-hour front desk, and freebies including WiFi and parking. Located 17 mi (27.3 km) from the heart of Chester. Monument Mountain Motel: Central Chester is 19.5 mi (31.4 km) away. Free WiFi and free parking are available during your stay, along with room amenities like free wired internet. River Valley Inn: 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.
What can I do in Chester?
Some outdoorsy places nearby include Pyramid Lake, County Beach, and Chesterfield Gorge. You'll find these family-friendly sights in the area: Berkshire Scenic Railway Museum, The Bookstore, and Bousquet Ski Area. While you're checking out the area, consider visiting Chester Town Hall, Kushi Institute, and Blandford Ski Area.
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.