Photo by Elizabeth Massa Peroulakis

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Check prices for these dates

Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan
In one month
6 Feb - 8 Feb
In two months
6 Mar - 8 Mar

Our top choices for Chester motels

In-room safe, desk, free cribs/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

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)
"Excellent location!!"
United States
Abdul Samad
The price is AED 275
AED 308 total
includes taxes & fees
6 Jan - 7 Jan
Travelodge by Wyndham Great Barrington Berkshires
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (813)
"Room was very well designed and clean. The woman who worked at the desk was wonderful!"
United States
Cynthia
Monument Mountain Motel
Basic Studio, 1 King Bed | Desk, laptop workspace, free WiFi, bed sheets
River Valley Inn

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.4 out of 10, Very Good, (102)
"Clean room, comfortable bed, nice shower! Owners were very nice - we will definitely stay here again!"
United States
Deb
The price is AED 364
AED 406 total
includes taxes & fees
6 Jan - 7 Jan
River Valley Inn
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
The price is AED 290
AED 324 total
includes taxes & fees
6 Jan - 7 Jan
Howard Johnson by Wyndham Lenox
Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
The Little Lion

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (548)
"Perfect for pets "
United States
Maria
The price is AED 404
AED 451 total
includes taxes & fees
6 Jan - 7 Jan
The Little Lion
Exterior
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1001)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is AED 191
AED 209 total
includes taxes & fees
9 Jan - 10 Jan
Pleasant Valley Motel West Stockbridge
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (841)
"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 AED 300
AED 335 total
includes taxes & fees
20 Jan - 21 Jan
Berkshire Inn
Seasonal outdoor pool
Sunset Inn

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (411)
"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 AED 331
AED 369 total
includes taxes & fees
6 Jan - 7 Jan
Sunset Inn
Reception
Elm Motel

Elm Motel

Elm Motel
2.0 star property
Westfield
7.2 out of 10, Good, (123)
"Very clean, lacking bathroom and bathroom storage. Good price."
United States
Daniel
The price is AED 364
AED 406 total
includes taxes & fees
31 Jan - 1 Feb
Elm Motel
Standard Room, 1 King Bed | Desk, iron/ironing board, free cribs/infant beds, rollaway beds
Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (653)
"The room was clean and the service adequate"
United States
David
The price is AED 263
AED 294 total
includes taxes & fees
18 Jan - 19 Jan
Econo Lodge Lee - Great Barrington
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Private kitchen | Mini-fridge, microwave, electric kettle
East Rock Inn

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (37)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is AED 463
AED 517 total
includes taxes & fees
20 Jan - 21 Jan
East Rock Inn
Exterior
Riverdale Inn

Riverdale Inn

Riverdale Inn
2.0 star property
West Springfield
5.8 out of 10, (1001)
"Staff was nice"
United States
Amanda
The price is AED 256
AED 293 total
includes taxes & fees
11 Jan - 12 Jan
Riverdale Inn
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (811)
"Room spotless and staff helpful."
United States
William
The price is AED 294
AED 329 total
includes taxes & fees
18 Jan - 19 Jan
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

Hotel Northampton

Hotel Northampton

10/10 Excellent
"Cute old hotel, room was small"
Chantal 2-night trip
Posted 16 hours ago
Hotel Northampton

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 843 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. Monument Mountain Motel: Free WiFi, free parking, and a picnic area are available during your stay. Central Chester is 19.5 mi (31.4 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. 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 air conditioning. 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, Chesterfield Gorge, and Otis Reservoir. 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, 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.