A snow-covered forest with a narrow stream running through it.

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Check prices for these dates

Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1

Our top choices for Chester motels

A building with a flat roof, multiple windows, and a satellite dish.

1. Becket Motel

Becket Motel
2.5 star property
Becket
6.6 out of 10, (63 reviews)
"Comfortable stay "
United States
Paul
The price is CA $137
CA $199 total
includes taxes & fees
Sep 8 - Sep 9
Becket Motel
A calm lake at dusk with a wooden dock and two chairs facing the water.

2. Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.6 out of 10, Exceptional, (14 reviews)
"excellent lakeside view"
United States
mike
The price is CA $190
CA $212 total
includes taxes & fees
Sep 7 - Sep 8
Berkshire Lake Lodge
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

3. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (908 reviews)
"Stay again"
United States
irene
The price is CA $108
CA $121 total
includes taxes & fees
Sep 7 - Sep 8
Howard Johnson by Wyndham Lenox
A round wooden table with two wine glasses and a green bottle, set against a window with a view of a blue railing and trees.

4. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (693 reviews)
"Have stayed here several times and it is a basic, decent place. It is in a great location, relatively clean and comfortable. Would return again."
United States
Anna
The price is CA $91
CA $101 total
includes taxes & fees
Sep 27 - Sep 28
Econo Lodge Lee - Great Barrington
A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.

5. Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (439 reviews)
"Host was very pleasant and extremely help with directions. Would definitely recommend"
United States
Joann
The price is CA $117
CA $131 total
includes taxes & fees
Sep 9 - Sep 10
Sunset Inn
A hotel room with two beds, a desk, a chair, a television, and a window with curtains.

6. River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.4 out of 10, Very good, (239 reviews)
"Big rooms, reasonable price, run by a nice family."
United States
Michael
The price is CA $126
CA $141 total
includes taxes & fees
Oct 7 - Oct 8
River Valley Inn
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

7. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (906 reviews)
"This motel is simple but has everything that you need for an inexpensive stay near Great Barrington."
United States
Charlie
The price is CA $118
CA $132 total
includes taxes & fees
Sep 7 - Sep 8
Monument Mountain Motel
A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

8. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.4 out of 10, Good, (612 reviews)
"Adequate but tired hotel. Not exceptionally clean."
United States
Nancy
The price is CA $116
CA $130 total
includes taxes & fees
Sep 7 - Sep 8
Travelodge by Wyndham Great Barrington Berkshires
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

9. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (917 reviews)
"Quiet location set back from road, comfortable beds and nice shower. Located right on Rt. 20 and near downtown."
United States
Ellen
The price is CA $115
CA $129 total
includes taxes & fees
Oct 7 - Oct 8
Berkshire Inn
A large house with a balcony and a grassy yard.

10. The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (607 reviews)
"Great location. Functional and affordable. Pet friendly."
United States
Anne
The price is CA $153
CA $171 total
includes taxes & fees
Sep 7 - Sep 8
The Little Lion
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

11. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (892 reviews)
"It was very nice and everyone was extremely helpful"
United States
ERICIA
The price is CA $84
CA $94 total
includes taxes & fees
Sep 7 - Sep 8
FairBridge Inn Express
A group of people performing yoga in an outdoor setting with grass and trees.

12. Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"The best aspect of this motel is the price. It is very close to the Tanglewood concert space and in West Stockbridge, a quaint town with galleries, a good bookstore, the excellent Turnpark Outdoor Sculpture Garden and "Amici" a nice Italian restaurant, etc."
United States
James
The price is CA $103
CA $113 total
includes taxes & fees
Sep 7 - Sep 8
Pleasant Valley Motel West Stockbridge
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

13. East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (53 reviews)
"great place!"
United States
ERIK
The price is CA $226
CA $252 total
includes taxes & fees
Sep 28 - Sep 29
East Rock Inn
A dark wooden TV stand with a flat-screen TV, a remote, and two cups.

14. Riverdale Inn

Riverdale Inn
2.0 star property
West Springfield
6.0 out of 10, (1,003 reviews)
"Staff is great ac works good rooms are just rooms parking is good very quiet for a night is just fine"
United States
renee
The price is CA $87
CA $100 total
includes taxes & fees
Oct 7 - Oct 8
Riverdale Inn
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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Top Chester Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"Excellent staff and excellent Indian restaurant!!! Hotel a little dated, but beds were comfortable and staff was great!"
Susan 1-night trip
Posted 3 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Chester

Chester Motels information

Number of reviews
3,855
Accommodation
23 Motels
Lowest Price
CA $94
Highest Price
CA $252

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 880 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. 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. River Valley 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. The Little Lion: Central Chester is 18.4 mi (29.6 km) away. Free WiFi and free parking are available during your stay, along with room amenities like a microwave. Howard Johnson by Wyndham Lenox: 17 mi (27.3 km) from the heart of Chester. Enjoy access to the free parking, 24-hour front desk, and coffee in the lobby.
What can I do in Chester?
Some outdoorsy places nearby include Becket Land Trust Historic Quarry, Otis Reservoir, and Goose Pond Reservation. You'll find these family-friendly sights in the area: Bousquet Ski Area, Berkshire Museum, and Berkshire Scenic Railway 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.

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