Photo by Elizabeth Massa Peroulakis

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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 23 Motels in Chester with updated reviews, rates, and availability.

Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (721)
"spacious room. "
The price is AED 253
AED 283 total
includes taxes & fees
11 May - 12 May
Howard Johnson by Wyndham Lenox
The Little Lion
Aerial view

The Little Lion

3.0 star property
8.8 out of 10, Excellent, (483)
"A cozy little inn! I recommend it! "
The price is AED 281
AED 314 total
includes taxes & fees
26 May - 27 May
The Little Lion
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, (712)
"Nice place and surrounding area "
The price is AED 279
AED 312 total
includes taxes & fees
12 May - 13 May
Monument Mountain Motel
River Valley Inn
Desk, laptop workspace, free WiFi, bed sheets

River Valley Inn

7.6 out of 10, Good, (12)
"The new owners of this property have done wonders. It’s clean, comfortable and affordable. It’s an easy ride from Northampton and many restaurants there. The owners were helpful and friendly and have big plans. I look forward to going back and seeing what other improvements they make"
The price is AED 474
AED 529 total
includes taxes & fees
11 May - 12 May
River Valley Inn
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

2.5 star property
5.4 out of 10, (714)
"Friendly staff and quick checkin "
The price is AED 261
AED 292 total
includes taxes & fees
23 May - 24 May
FairBridge Inn Express
Berkshire Inn
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (766)
"They did a fine job. The property was dated, but well kept. There is a bit of road traffic noise. It was a very good value. "
The price is AED 287
AED 321 total
includes taxes & fees
11 May - 12 May
Berkshire Inn
Riverdale Inn
Exterior

Riverdale Inn

2.0 star property
5.8 out of 10, (1000)
"Staff very friendly good cleaning services "
The price is AED 308
AED 353 total
includes taxes & fees
25 May - 26 May
Riverdale Inn
Pleasant Valley Motel West Stockbridge
Garden view

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (965)
"Easy access to the Massachusetts Turnpike and less than 10 miles away from the tourist options I selected."
The price is AED 239
AED 262 total
includes taxes & fees
14 May - 15 May
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, (590)
"Everyone was nice and the service was great"
The price is AED 238
AED 266 total
includes taxes & fees
18 May - 19 May
Econo Lodge Lee - Great Barrington
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (381)
"We had a quick overnight in the area & this motel was a good value. Close to the highway & walking distance to restaurants, coffee & town. Check in was easy, staff is very kind & friendly. Our room was very basic but spacious & clean. We slept well. We would definitely stay here again. "
The price is AED 314
AED 351 total
includes taxes & fees
11 May - 12 May
Sunset Inn
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (603)
"Great location. Pleasant staff."
The price is AED 253
AED 283 total
includes taxes & fees
11 May - 12 May
Wagon Wheel Inn
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, (523)
"The staff was very friendly and the room was clean. "
The price is AED 253
AED 283 total
includes taxes & fees
11 May - 12 May
Travelodge by Wyndham Great Barrington Berkshires
East Rock Inn
Exterior

East Rock Inn

2.0 star property
9.4 out of 10, Exceptional, (24)
"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 AED 469
AED 524 total
includes taxes & fees
15 May - 16 May
East Rock Inn
Heart of the Berkshires
Economy Cabin | Premium bedding, individually decorated, free WiFi, bed sheets

Heart of the Berkshires

9.4 out of 10, Exceptional, (3)
"Was great comfy quiet "
Heart of the Berkshires
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. "
The price is AED 327
AED 365 total
includes taxes & fees
25 May - 26 May
Elm Motel
Express Inn
Standard Double Room | Bathroom | Shower, towels

Express Inn

2.0 star property
2.0 out of 10, (1)
"Gross, gross, gross. "
Express Inn
Becket Motel
Front of property

Becket Motel

2.5 star property
6.6 out of 10, (55)
"Comfortable stay "
The price is AED 349
AED 513 total
includes taxes & fees
18 May - 19 May
Becket 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
Standard Room, 1 Queen Bed, Non Smoking, Jetted Tub | 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
Exterior

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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Other property types in Chester

The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
Deluxe Queen Room with 2 Queen Beds
1 bedroom, WiFi, bed sheets

Deluxe Queen Room with 2 Queen Beds

2.0 star property
The price is AED 437
AED 570 total
includes taxes & fees
11 May - 12 May
Deluxe Queen Room with 2 Queen Beds
Cozy Home in Holyoke with 2 bedrooms
Fridge, microwave, oven, stovetop

Cozy Home in Holyoke with 2 bedrooms

10.0 out of 10, Exceptional, (4)
"We stayed in Holyoke as my daughter was performing at UMASS Amherst and this was a great location only 25 minutes of so away from campus. The home is spacious with two bedrooms and bathrooms. A very clean and well maintained the home. Would definitely recommend and will visit again!! "
The price is AED 477
AED 1,063 total
includes taxes & fees
12 May - 13 May
Cozy Home in Holyoke with 2 bedrooms
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.

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 822 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. Howard Johnson by Wyndham Lenox is located 17 mi (27.3 km) from the heart of Chester. Enjoy access to the 24-hour front desk, and freebies including WiFi and parking. Riverdale Inn: Free WiFi and free parking are available during your stay, along with room amenities like air conditioning. Central Chester is 20.2 mi (32.5 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. 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. Monument Mountain Motel: 19.5 mi (31.4 km) from the heart of Chester. Enjoy access to the picnic area, and freebies including WiFi and parking.
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: Congregation Beth Israel, Bousquet Ski Area, and Spare Time Bowling. While you’re checking out the area, consider visiting Chester Town Hall, Jacob’s Pillow, and County Beach.
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.