Photo by Elizabeth Massa Peroulakis

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Check prices for these dates

Next weekend
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

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, (716)
"No issues"
The price is SAR 259
SAR 289 total
includes taxes & fees
31 Mar - 1 Apr
Howard Johnson by Wyndham Lenox
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, (706)
"I've stayed here many times for both brief stays and full weeks. Never disappointed. Affordable, clean family-run operation. The only place I stay in the Berkshires. "
The price is SAR 249
SAR 279 total
includes taxes & fees
31 Mar - 1 Apr
Monument Mountain Motel
The Little Lion
Exterior

The Little Lion

3.0 star property
8.8 out of 10, Excellent, (475)
"Enjoyed it alot"
The price is SAR 319
SAR 356 total
includes taxes & fees
6 Apr - 7 Apr
The Little Lion
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 SAR 323
SAR 360 total
includes taxes & fees
31 Mar - 1 Apr
Berkshire Inn
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

2.5 star property
5.4 out of 10, (709)
"Friendly staff and quick checkin "
The price is SAR 259
SAR 289 total
includes taxes & fees
31 Mar - 1 Apr
FairBridge Inn Express
Hatfield Inn
Desk, laptop workspace, free WiFi, bed sheets

Hatfield Inn

8.8 out of 10, Excellent, (3)
"I was very surprised upon arrival how kept the place was. The room had all the heat needed. The most shocking was how hot the water was. I paid for most expensive hotels, and the water was hot like this place. It was pleasant to meet the manager, who went out his way, to make sure i could get a early check-in, during the upcoming snow storm. Thanks for the stay. "
The price is SAR 446
SAR 499 total
includes taxes & fees
30 Mar - 31 Mar
Hatfield Inn
Riverdale Inn
Exterior

Riverdale Inn

2.0 star property
5.8 out of 10, (999)
"Eh"
The price is SAR 366
SAR 419 total
includes taxes & fees
30 Mar - 31 Mar
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 SAR 228
SAR 250 total
includes taxes & fees
29 Mar - 30 Mar
Pleasant Valley Motel West Stockbridge
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.2 out of 10, Good, (600)
"Great location. Pleasant staff."
The price is SAR 259
SAR 289 total
includes taxes & fees
27 Mar - 28 Mar
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, (522)
"The staff are all very nice & the rooms are always clean. The hotel is conveniently located & easy to find. This is our second stay here. "
The price is SAR 281
SAR 314 total
includes taxes & fees
29 Mar - 30 Mar
Travelodge by Wyndham Great Barrington Berkshires
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 SAR 244
SAR 272 total
includes taxes & fees
23 Mar - 24 Mar
Econo Lodge Lee - Great Barrington
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (380)
"The room was clean and perfect for our stay."
The price is SAR 308
SAR 344 total
includes taxes & fees
23 Mar - 24 Mar
Sunset Inn
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 SAR 468
SAR 523 total
includes taxes & fees
14 Apr - 15 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 SAR 317
SAR 411 total
includes taxes & fees
23 Mar - 24 Mar
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 SAR 356
SAR 524 total
includes taxes & fees
2 Apr - 3 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, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is SAR 563
SAR 859 total
includes taxes & fees
23 Mar - 24 Mar
Berkshire Village Carriage House - Super Private!!
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player

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 796 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. The Little Lion is located 18.4 mi (29.6 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. 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. Hatfield Inn: Central Chester is 18.6 mi (29.9 km) away. Free WiFi and free parking are available during your stay, along with room amenities like a microwave. 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: Bousquet Ski Area, Spare Time Bowling, 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.