Photo by Elizabeth Massa Peroulakis

Search Motels in Chester

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

Monument Mountain Motel
Room

Monument Mountain Motel

2.5 star property
8.8 out of 10, Excellent, (697)
"Rooms have been recently renovated and were clean and spotless. Great comfortable room with convenient gas station and sandwich shop across the street as well as several other eateries close by. Owner and staff were very friendly and made me feel welcome. I will definitely come back here in the future...... Good job 👍"
The price is SAR 250
SAR 279 total
includes taxes & fees
12 Jan - 13 Jan
Monument Mountain Motel
FairBridge Inn Express
Room

FairBridge Inn Express

2.5 star property
5.4 out of 10, (695)
"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 SAR 259
SAR 289 total
includes taxes & fees
12 Jan - 13 Jan
FairBridge Inn Express
The Little Lion
Exterior

The Little Lion

3.0 star property
8.8 out of 10, Excellent, (446)
"It was fine for the price and location Would stay there again! "
The price is SAR 239
SAR 267 total
includes taxes & fees
26 Jan - 27 Jan
The Little Lion
Riverdale Inn
Exterior

Riverdale Inn

2.0 star property
5.8 out of 10, (999)
"Never cleaned my room "
The price is SAR 367
SAR 420 total
includes taxes & fees
12 Jan - 13 Jan
Riverdale Inn
Howard Johnson by Wyndham Lenox
Outdoor pool

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (705)
"The room was clean and spacious. The parking lot still had a lot of snow and especially ice"
The price is SAR 297
SAR 331 total
includes taxes & fees
12 Jan - 13 Jan
Howard Johnson by Wyndham Lenox
Berkshire Inn
Outdoor pool

Berkshire Inn

2.0 star property
7.6 out of 10, Good, (759)
"Nice area "
The price is SAR 323
SAR 361 total
includes taxes & fees
13 Jan - 14 Jan
Berkshire Inn
East Rock Inn
Exterior

East Rock Inn

2.0 star property
9.2 out of 10, Wonderful, (15)
"Love this motel. Visit the area monthly, this was my 5th visit at East Rock, every time has been perfect."
The price is SAR 476
SAR 532 total
includes taxes & fees
28 Jan - 29 Jan
East Rock Inn
Econo Lodge Lee - Great Barrington
Exterior

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (582)
"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 SAR 225
SAR 252 total
includes taxes & fees
12 Jan - 13 Jan
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, (514)
"Very clean and staff very helpful"
The price is SAR 282
SAR 315 total
includes taxes & fees
12 Jan - 13 Jan
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 SAR 259
SAR 289 total
includes taxes & fees
12 Jan - 13 Jan
Wagon Wheel Inn
Pleasant Valley Motel West Stockbridge
Exterior

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (958)
"The room and bathroom were very clean. "
The price is SAR 221
SAR 243 total
includes taxes & fees
16 Jan - 17 Jan
Pleasant Valley Motel West Stockbridge
Sunset Inn
Outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (378)
"Quick and easy check in! The manager was friendly and helpful. "
The price is SAR 288
SAR 322 total
includes taxes & fees
14 Jan - 15 Jan
Sunset Inn
Heart of the Berkshires
Front of property

Heart of the Berkshires

9.0 out of 10, Wonderful, (2)
"Very cute décor, not the most comfortable or fresh, but clean and easy self check in/out system (door has a code which is communicated in advance). Lots of food options short drive away."
The price is SAR 261
SAR 345 total
includes taxes & fees
14 Jan - 15 Jan
Heart of the Berkshires
Express Inn
Exterior

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 SAR 364
SAR 533 total
includes taxes & fees
12 Jan - 13 Jan
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 SAR 334
SAR 373 total
includes taxes & fees
12 Jan - 13 Jan
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, (234)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is SAR 563
SAR 851 total
includes taxes & fees
12 Jan - 13 Jan
Berkshire Village Carriage House - Super Private!!
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
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 794 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. 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. The Little Lion: Enjoy access to the picnic area, and freebies including WiFi and parking. Located 18.4 mi (29.6 km) from the heart of Chester. Howard Johnson by Wyndham Lenox: Central Chester is 17 mi (27.3 km) away. Free WiFi and free parking are available during your stay, along with room amenities like a soaking tub. Berkshire Inn: 18.4 mi (29.6 km) from the heart of Chester. Enjoy access to the seasonal outdoor pool, and freebies including WiFi and parking.
What can I do in Chester?
Some outdoorsy places nearby include Iroquis Waterfront, Otis Reservoir, and October Mountain State Forest. You’ll find these family-friendly sights in the area: The Bookstore, Bousquet Ski Area, and Berkshire Museum. 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.