Photo by Elizabeth Massa Peroulakis

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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

Compare 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, (717)
"Staff friendly. Room comfortable. Location great."
The price is AED 275
AED 308 total
includes taxes & fees
1 May - 2 May
Howard Johnson by Wyndham Lenox
The Little Lion
Aerial view

The Little Lion

3.0 star property
8.8 out of 10, Excellent, (477)
"Enjoyed it alot"
The price is AED 281
AED 314 total
includes taxes & fees
23 Apr - 24 Apr
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, (708)
"Manager (owner?) was friendly and helpful. Room was clean and spacious (had corner room). Very good for price. Some annoying ticking sound maybe from room heater throughout the night but otherwise no issues at all. Would stay here again."
The price is AED 244
AED 273 total
includes taxes & fees
10 Apr - 11 Apr
Monument Mountain Motel
Hatfield Inn
Desk, laptop workspace, free WiFi, bed sheets

Hatfield Inn

8.4 out of 10, Very Good, (6)
"I slept like a rock. The bed was comfy and the room was clean and quiet."
The price is AED 437
AED 488 total
includes taxes & fees
10 Apr - 11 Apr
Hatfield Inn
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

2.5 star property
5.4 out of 10, (711)
"Friendly staff and quick checkin "
The price is AED 255
AED 285 total
includes taxes & fees
11 Apr - 12 Apr
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, (764)
"The room was very clean "
The price is AED 316
AED 353 total
includes taxes & fees
10 Apr - 11 Apr
Berkshire Inn
Riverdale Inn
Exterior

Riverdale Inn

2.0 star property
5.8 out of 10, (1000)
"Was able to check in super early. Outside looks blah. Inside is super clean and nice"
The price is AED 308
AED 353 total
includes taxes & fees
22 Apr - 23 Apr
Riverdale Inn
Pleasant Valley Motel West Stockbridge
Garden view

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (964)
"The room and bathroom were very clean. "
The price is AED 223
AED 245 total
includes taxes & fees
14 Apr - 15 Apr
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, (587)
"While the gentleman at the front desk can be a bit cold, the women that work at the property are very pleasant. They were super accommodating and did a nice job cleaning the room during our stay. The room was a good value and provided a nice place for our family of 5 plus a small dog to lay our heads at night."
The price is AED 248
AED 277 total
includes taxes & fees
16 Apr - 17 Apr
Econo Lodge Lee - Great Barrington
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (380)
"Quick and easy check in! The manager was friendly and helpful. "
The price is AED 307
AED 343 total
includes taxes & fees
13 Apr - 14 Apr
Sunset Inn
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (601)
"Great location. Pleasant staff."
The price is AED 217
AED 242 total
includes taxes & fees
10 Apr - 11 Apr
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 275
AED 308 total
includes taxes & fees
10 Apr - 11 Apr
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 459
AED 512 total
includes taxes & fees
23 Apr - 24 Apr
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 "
The price is AED 342
AED 439 total
includes taxes & fees
10 Apr - 11 Apr
Heart of the Berkshires
Elm Motel
Reception

Elm Motel

2.0 star property
7.0 out of 10, Good, (122)
"Cute remodeled rooms, the exterior reminds you of a 60's motel, but step inside to a cute remodeled room, new floors, new fixtures, bathroom, I will definitely stay there again"
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)
"I liked how there was walking trails and shopping near by. "
The price is AED 349
AED 513 total
includes taxes & fees
10 Apr - 11 Apr
Becket Motel
Lantern House Motel
Exterior

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
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (241)
"This beautiful carriage house is ingeniously designed with no wasted space. Surrounded by nature, it is totally private, yet it is two minutes from shops and restaurants. The window seats are sublime and the heated floors offered relief after afternoons spent hiking in the cold. "
The price is AED 551
AED 841 total
includes taxes & fees
10 Apr - 11 Apr
Berkshire Village Carriage House - Super Private!!
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Terrace/patio

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (61)
"3 day holiday getaway, my husband and our 2 pups. A hike in nearby trails in the woods, enjoyed Lee downtown eateries and shops. Beautiful winter wonderland in the Berkshires. The guest rental was perfect!!! Warm, spacious, comfortable, perfect location. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
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 801 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. 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. Hatfield 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. 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. FairBridge Inn Express: 17.4 mi (28 km) from the heart of Chester. Enjoy access to the business center, 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.