Photo by Elizabeth Massa Peroulakis

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Compare 19 Motels in Chester with updated reviews, rates, and availability.

Howard Johnson by Wyndham Lenox
Outdoor pool

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (703)
"Manager was helpful. The heating system was loud and although the manager tried to fix it , the noise disrupted sleep. "
The price is AED 290
AED 324 total
includes taxes & fees
2 Jan - 3 January 2025
Howard Johnson by Wyndham Lenox
Monument Mountain Motel
Room

Monument Mountain Motel

2.5 star property
8.8 out of 10, Excellent, (691)
"went for a quick ski overnight. the motel was very clean, in good shape, quiet, pleasant check in/out experience, free coffee, everything in the room worked, the water was hot the pressure was good there was a fridge and microwave and blowdryer, comfy bed, plenty of hanging closet space, a little table and chair area by the front window, a nice view of the playground, good heating unit, and very convenient to everything you need and want to do here, and most of all affordable including my...
The price is AED 244
AED 273 total
includes taxes & fees
1 Jan - 2 January 2025
Monument Mountain Motel
Riverdale Inn
Exterior

Riverdale Inn

2.0 star property
5.8 out of 10, (997)
"Never cleaned my room "
The price is AED 359
AED 411 total
includes taxes & fees
26 Dec - 27 Dec
Riverdale Inn
FairBridge Inn Express
Room

FairBridge Inn Express

2.5 star property
5.4 out of 10, (686)
"I don’t know so many complaints. Bed was good, clean. Plenty of park. Provided what we paid for and was expecting. "
The price is AED 253
AED 283 total
includes taxes & fees
27 Dec - 28 Dec
FairBridge Inn Express
The Little Lion
Exterior

The Little Lion

3.0 star property
8.8 out of 10, Excellent, (443)
"The location was great, and being pet friendly was a Pius."
The price is AED 281
AED 314 total
includes taxes & fees
7 Jan - 8 January 2025
The Little Lion
Berkshire Inn
Outdoor pool

Berkshire Inn

2.0 star property
7.6 out of 10, Good, (753)
"This is a nice motel, though there is no continental breakfast. There is a pot of coffee made at 7am. The rooms are clean and updated, the mattress is good, airconditioner in back wall, simple round thermostat for hot water radiator heating, mini-fridge is compressor type, microwave."
The price is AED 316
AED 353 total
includes taxes & fees
30 Dec - 31 Dec
Berkshire Inn
Econo Lodge Lee - Great Barrington
Exterior

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (581)
"Was convenient and inexpensive. The back stairs were a little rickety. Also had to ring the bell to check in later in the evening, but was fine. Room was just the basics, but served the purpose for my one night stay. "
The price is AED 220
AED 246 total
includes taxes & fees
30 Dec - 31 Dec
Econo Lodge Lee - Great Barrington
Travelodge by Wyndham Great Barrington Berkshires
Exterior

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.6 out of 10, Good, (512)
"Room was very clean and reception most welcome, and a very reasonable price and stay."
The price is AED 253
AED 283 total
includes taxes & fees
29 Dec - 30 Dec
Travelodge by Wyndham Great Barrington Berkshires
Wagon Wheel Inn
Exterior

Wagon Wheel Inn

2.0 star property
7.2 out of 10, Good, (597)
"Great location. Pleasant staff."
The price is AED 253
AED 283 total
includes taxes & fees
31 Dec - 1 January 2025
Wagon Wheel Inn
Pleasant Valley Motel West Stockbridge
Exterior

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (956)
"Well located near attractions "
The price is AED 217
AED 238 total
includes taxes & fees
31 Dec - 1 January 2025
Pleasant Valley Motel West Stockbridge
East Rock Inn
Front of property

East Rock Inn

2.0 star property
9.4 out of 10, Exceptional, (13)
"Love this motel. Visit the area monthly, this was my 5th visit at East Rock, every time has been perfect."
The price is AED 436
AED 487 total
includes taxes & fees
13 Jan - 14 January 2025
East Rock Inn
Sunset Inn
Outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (376)
"When we arrived, the receptionist was pleasant and kind, our room was ready. When we asked for more towels, we did not have to wait for more than 5 minutes and we had them. The restaurant next door, Rose's cafe, is amazing!"
The price is AED 293
AED 328 total
includes taxes & fees
1 Jan - 2 January 2025
Sunset Inn
Express Inn
Exterior

Express Inn

2.0 star property
2.0 out of 10, (1)
"Gross, gross, gross. "
Express Inn
Heart of the Berkshires
Front of property

Heart of the Berkshires

The price is AED 232
AED 310 total
includes taxes & fees
30 Dec - 31 Dec
Heart of the Berkshires
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 338
AED 501 total
includes taxes & fees
28 Dec - 29 Dec
Becket Motel
Elm Motel
Exterior

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"
The price is AED 327
AED 365 total
includes taxes & fees
24 Jan - 25 January 2025
Elm Motel
Lantern House Motel
Room

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
Front of property

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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Other property types in Chester

Cozy Berkshires Vacation Rental Near Hiking!
Chester Vacation Rental | 2BR | 1BA | 2,000 Sq Ft | Stairs Required

Cozy Berkshires Vacation Rental Near Hiking!

10.0 out of 10, Exceptional, (1)
"The stay at the property was enjoyable. The space was large, spacious and very clean. Two people were able to stay quite comfortably."
Cozy Berkshires Vacation Rental Near Hiking!
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (232)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is AED 536
AED 821 total
includes taxes & fees
30 Dec - 31 Dec
Berkshire Village Carriage House - Super Private!!
Peace and quiet on the lake
Exterior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (200)
"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"
Peace and quiet on the lake
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 793 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. Monument Mountain Motel is located 19.5 mi (31.4 km) from the heart of Chester. Enjoy access to the picnic area, and freebies including WiFi and parking. Howard Johnson by Wyndham Lenox: Free WiFi, free parking, and a 24-hour front desk are available during your stay. Central Chester is 17 mi (27.3 km) away. Riverdale Inn: Enjoy access to the 24-hour front desk, and freebies including WiFi and parking. Located 20.2 mi (32.5 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. The Little Lion: 18.4 mi (29.6 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 Skyline Trail. 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, 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.