Photo by Elizabeth Massa Peroulakis

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Check prices for these dates

Next weekend
4 Jul - 6 Jul
In two weeks
11 Jul - 13 Jul
In one month
25 Jul - 27 Jul
In two months
22 Aug - 24 Aug

Motels in Chester

Riverdale Inn
Exterior

Riverdale Inn

2.0 star property
5.8 out of 10, (1000)
"It’s a great place to stay "
The price is SAR 315
SAR 360 total
includes taxes & fees
29 Jun - 30 Jun
Riverdale Inn
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (728)
"Friendly staff and quick checkin "
The price is SAR 267
SAR 298 total
includes taxes & fees
10 Jul - 11 Jul
FairBridge Inn Express
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (740)
"Was great loved the jacuzzi tub "
The price is SAR 371
SAR 415 total
includes taxes & fees
29 Jun - 30 Jun
Howard Johnson by Wyndham Lenox
Berkshire Inn
1 bedroom, desk, iron/ironing board, free WiFi

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (774)
"The motel was nicely done and clean. The beds were comfortable "
The price is SAR 338
SAR 377 total
includes taxes & fees
8 Jul - 9 Jul
Berkshire Inn
The Little Lion
Pet-friendly

The Little Lion

3.0 star property
8.8 out of 10, Excellent, (501)
"Convenience of contactless check in and driving up to door"
The price is SAR 600
SAR 670 total
includes taxes & fees
1 Jul - 2 Jul
The Little Lion
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, (528)
"No rooms available despite reservations "
The price is SAR 371
SAR 415 total
includes taxes & fees
30 Jun - 1 Jul
Travelodge by Wyndham Great Barrington Berkshires
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
8.8 out of 10, Excellent, (721)
"Clean, warm, comfy bedding. Bathroom spotless. Friendly management."
Monument Mountain Motel
Pleasant Valley Motel West Stockbridge
Garden view

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (973)
"Great location for my activities."
The price is SAR 261
SAR 286 total
includes taxes & fees
6 Jul - 7 Jul
Pleasant Valley Motel West Stockbridge
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
6.2 out of 10, (600)
"Affordable"
The price is SAR 239
SAR 267 total
includes taxes & fees
10 Jul - 11 Jul
Econo Lodge Lee - Great Barrington
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (381)
"The room was clean and perfect for our stay."
The price is SAR 356
SAR 398 total
includes taxes & fees
7 Jul - 8 Jul
Sunset Inn
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (606)
"Fix sink faucet in room #2. Otherwise worked great for just a place to sleep. Shower made up for having to shave in cold water."
The price is SAR 259
SAR 289 total
includes taxes & fees
29 Jun - 30 Jun
Wagon Wheel Inn
River Valley Inn
1 bedroom, desk, laptop workspace, free WiFi

River Valley Inn

2.0 star property
8.2 out of 10, Very Good, (20)
"Thoroughly enjoyed my stay at the River Valley Inn. Our hosts were very pleasant. The room was clean and comfortable. Will definitely stay again when in the area. "
The price is SAR 484
SAR 540 total
includes taxes & fees
29 Jun - 30 Jun
River Valley Inn
East Rock Inn
Premium Apartment | Private kitchen | Electric kettle

East Rock Inn

2.0 star property
9.4 out of 10, Exceptional, (25)
"The property is well maintained and set back from the road. It was very quiet and the rooms are fantastic. A must stay if you are going to be in the area. "
The price is SAR 630
SAR 704 total
includes taxes & fees
2 Jul - 3 Jul
East Rock Inn
Becket Motel
Front of property

Becket Motel

2.5 star property
6.6 out of 10, (55)
"Comfortable stay "
The price is SAR 370
SAR 539 total
includes taxes & fees
2 Jul - 3 Jul
Becket Motel
Elm Motel
Reception

Elm Motel

2.0 star property
7.0 out of 10, Good, (122)
"Jeannie at the front desk was helpful and very welcoming. Room was renovated since my last visit. "
Elm Motel
Express Inn
Exterior

Express Inn

2.0 star property
2.0 out of 10, (1)
"Gross, gross, gross. "
Express Inn
Heart of the Berkshires
Economy Cabin | 1 bedroom, premium bedding, individually decorated, free WiFi

Heart of the Berkshires

7.2 out of 10, Good, (5)
"Was great comfy quiet "
Heart of the Berkshires
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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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. 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. 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. Pleasant Valley Motel West Stockbridge: 19.8 mi (31.9 km) from the heart of Chester. Enjoy access to the free WiFi and free parking, as well as room amenities like a microwave.
What can I do in Chester?
Some outdoorsy places nearby include Glendale Falls, Iroquis Waterfront, and Pyramid Lake. 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, Jacob's Pillow, and Otis Ridge.
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.