Photo by Elizabeth Massa Peroulakis

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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

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

FairBridge Inn Express
Room

FairBridge Inn Express

2.5 star property
5.4 out of 10, (703)
"Quiet "
The price is SAR 233
SAR 260 total
includes taxes & fees
2 Mar - 3 Mar
FairBridge Inn Express
Monument Mountain Motel
Room

Monument Mountain Motel

2.5 star property
8.8 out of 10, Excellent, (700)
"Small but clean. Good mattress. Very reasonable price"
The price is SAR 249
SAR 279 total
includes taxes & fees
23 Feb - 24 Feb
Monument Mountain Motel
Howard Johnson by Wyndham Lenox
Outdoor pool

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (713)
"spacious room. "
The price is SAR 296
SAR 331 total
includes taxes & fees
18 Feb - 19 Feb
Howard Johnson by Wyndham Lenox
The Little Lion
Exterior

The Little Lion

3.0 star property
8.8 out of 10, Excellent, (472)
"A cozy quiet charming place to stay."
The price is SAR 239
SAR 267 total
includes taxes & fees
2 Mar - 3 Mar
The Little Lion
Berkshire Inn
Outdoor pool

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (763)
"The room was very clean "
The price is SAR 323
SAR 360 total
includes taxes & fees
18 Feb - 19 Feb
Berkshire Inn
East Rock Inn
Exterior

East Rock Inn

2.0 star property
9.4 out of 10, Exceptional, (21)
"Good "
The price is SAR 457
SAR 510 total
includes taxes & fees
20 Mar - 21 Mar
East Rock Inn
Travelodge by Wyndham Great Barrington Berkshires
Exterior

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.6 out of 10, Good, (517)
"Convenient. Wouldn’t work for me at other visits as I have had to check in late at night and the desk is only staffed certain hours but was perfect for this trip. "
The price is SAR 281
SAR 314 total
includes taxes & fees
23 Feb - 24 Feb
Travelodge by Wyndham Great Barrington Berkshires
Riverdale Inn
Exterior

Riverdale Inn

2.0 star property
5.8 out of 10, (1000)
"Eh"
The price is SAR 330
SAR 377 total
includes taxes & fees
2 Mar - 3 Mar
Riverdale Inn
Wagon Wheel Inn
Exterior

Wagon Wheel Inn

2.0 star property
7.2 out of 10, Good, (599)
"Great location. Pleasant staff."
The price is SAR 259
SAR 289 total
includes taxes & fees
18 Feb - 19 Feb
Wagon Wheel Inn
Pleasant Valley Motel West Stockbridge
Exterior

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (963)
"The room and bathroom were very clean. "
The price is SAR 228
SAR 250 total
includes taxes & fees
22 Feb - 23 Feb
Pleasant Valley Motel West Stockbridge
Econo Lodge Lee - Great Barrington
Exterior

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (585)
"It was close to Butternut on a snowy day. Very good for the value and what it is."
The price is SAR 259
SAR 289 total
includes taxes & fees
18 Feb - 19 Feb
Econo Lodge Lee - Great Barrington
Heart of the Berkshires
Front of property

Heart of the Berkshires

9.4 out of 10, Exceptional, (3)
"Was great comfy quiet "
The price is SAR 277
SAR 363 total
includes taxes & fees
18 Feb - 19 Feb
Heart of the Berkshires
Sunset Inn
Outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (379)
"I think some of the unfavorable reviews I have seen are unfair. Everything is relative and, yes, this is clearly an older property that appears to be privately owned. Notwithstanding its age and some of the dated decor and furnishing, my room was very clean (cleaner than some I have stayed in at upscale hotels). It was one of the coldest nights of the year and the heat worked well and the water was hot. The television and WiFi worked and for my purposes (a one night layover on my way to visit...
The price is SAR 270
SAR 302 total
includes taxes & fees
1 Mar - 2 Mar
Sunset Inn
Express Inn
Exterior

Express Inn

2.0 star property
2.0 out of 10, (1)
"Gross, gross, gross. "
Express Inn
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 371
SAR 415 total
includes taxes & fees
25 Feb - 26 Feb
Elm Motel
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 345
SAR 511 total
includes taxes & fees
18 Feb - 19 Feb
Becket 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

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
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
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is SAR 563
SAR 855 total
includes taxes & fees
20 Feb - 21 Feb
Berkshire Village Carriage House - Super Private!!
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 791 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. FairBridge Inn Express is located 17.4 mi (28 km) from the heart of Chester. Enjoy access to the business center, 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. Monument Mountain Motel: Enjoy access to the picnic area, and freebies including WiFi and parking. Located 19.5 mi (31.4 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 Glendale Falls, Iroquis Waterfront, and Pyramid Lake. 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, Blandford Ski Area, and Jacob’s Pillow.
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.