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Check prices for these dates

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28 Nov - 30 Nov
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5 Dec - 7 Dec
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19 Dec - 21 Dec
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16 Jan - 18 Jan

Motels in Chester

Basic Studio, 1 King Bed | Desk, laptop workspace, free WiFi, bed sheets
River Valley Inn

River Valley Inn

2.0 star property
West Hatfield
8.6 out of 10, Excellent, (97)
"Clean room, comfortable bed, nice shower! Owners were very nice - we will definitely stay here again!"
United States
Deb
The price is AED 400
AED 447 total
includes taxes & fees
20 Nov - 21 Nov
River Valley Inn
Room, 1 Queen Bed, 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, (791)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
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, (559)
"The staff were very friendly and accommodating "
United States
Tom
The price is AED 275
AED 308 total
includes taxes & fees
23 Nov - 24 Nov
Travelodge by Wyndham Great Barrington Berkshires
Seasonal outdoor pool
Sunset Inn

Sunset Inn

2.0 star property
Lee
7.6 out of 10, Good, (410)
"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 314
AED 351 total
includes taxes & fees
3 Dec - 4 Dec
Sunset Inn
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (824)
"Staff was very friendly and helpful."
United States
Pamela
The price is AED 290
AED 324 total
includes taxes & fees
20 Nov - 21 Nov
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, (838)
"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 279
AED 312 total
includes taxes & fees
24 Nov - 25 Nov
Berkshire Inn
Exterior
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2.0 star property
West Stockbridge
6.8 out of 10, (1001)
"good average place to stay."
United States
Terry
The price is AED 223
AED 245 total
includes taxes & fees
25 Nov - 26 Nov
Pleasant Valley Motel West Stockbridge
Property grounds
Wagon Wheel Inn

Wagon Wheel Inn

2.0 star property
Lenox
7.0 out of 10, Good, (641)
"Beautiful area. Close to Mt. Greylock, Octobrr Mountain and Pleasant Valley Audubon."
United States
Benjamin
The price is AED 253
AED 283 total
includes taxes & fees
24 Nov - 25 Nov
Wagon Wheel Inn
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

2.0 star property
Lee
6.4 out of 10, (647)
"Great place. , good staff "
United States
ketul
The price is AED 215
AED 241 total
includes taxes & fees
2 Dec - 3 Dec
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

2.0 star property
Great Barrington
9.4 out of 10, Exceptional, (36)
"We had a great stay at East Rock Inn! Newly remodeled, clean room, comfortable bed, easy access to town. I will definitely stay there again."
United States
Laura
The price is AED 463
AED 517 total
includes taxes & fees
20 Dec - 21 Dec
East Rock Inn
Front of property
Becket Motel

Becket Motel

2.5 star property
Becket
6.8 out of 10, (60)
"Comfortable stay "
United States
Paul
The price is AED 328
AED 489 total
includes taxes & fees
20 Nov - 21 Nov
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, (810)
"Room spotless and staff helpful."
United States
William
The price is AED 275
AED 308 total
includes taxes & fees
20 Nov - 21 Nov
FairBridge Inn Express
Exterior
Riverdale Inn

Riverdale Inn

2.0 star property
West Springfield
5.8 out of 10, (1000)
"Staff was nice"
United States
Amanda
The price is AED 308
AED 353 total
includes taxes & fees
20 Nov - 21 Nov
Riverdale Inn
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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"Clean, cozy, workers are very attentive. The bar and activity center is a lot of fun. "
Paige 2-night trip
Posted 2 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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 840 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. FairBridge Inn Express: Free WiFi and free parking are available during your stay, along with room amenities like a microwave. Central Chester is 17.4 mi (28 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 Littleville Lake, Pyramid Lake, 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.