Find Cheshire motels from $58

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Motels in Cheshire

Exterior
The Villager Motel

The Villager Motel

2.0 star property
Williamstown
8.8 out of 10, Excellent, (764)
"It's very good for stay over"
United States
Frances
$69 nightly
The price is $77
Dec 8 - Dec 9
Total with taxes and fees
The Villager Motel
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn

Berkshire Inn

2.0 star property
Pittsfield
7.8 out of 10, Good, (840)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
$81 nightly
The price is $91
Jan 5 - Jan 6, 2026
Total with taxes and fees
Berkshire Inn
Exterior
Cozy Corner Motel

Cozy Corner Motel

2.0 star property
Williamstown
9.2 out of 10, Wonderful, (884)
"Clean, Great Staff, Quiet"
United States
john
$79 nightly
The price is $88
Dec 10 - Dec 11
Total with taxes and fees
Cozy Corner Motel
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (827)
"Staff was very friendly and helpful."
United States
Pamela
$79 nightly
The price is $88
Dec 8 - Dec 9
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Courtyard
The Springs Motel

The Springs Motel

2.0 star property
New Ashford
9.2 out of 10, Wonderful, (87)
"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
$103 nightly
The price is $114
Dec 9 - Dec 10
Total with taxes and fees
The Springs Motel
Exterior detail
Maple Terrace Motel

Maple Terrace Motel

2.5 star property
Williamstown
9.6 out of 10, Exceptional, (588)
"Reception was great, lovely beds (most important to me), great location, this place is excellent."
United States
William
$99 nightly
The price is $111
Dec 8 - Dec 9
Total with taxes and fees
Maple Terrace Motel
Exterior detail
Williamstown Motel

Williamstown Motel

2.0 star property
Williamstown
9.4 out of 10, Exceptional, (314)
"Was upgraded to a larger room for no special reason. Very nice proprietor. For budget priced accommodations, this is an excellent value. Would definitely stay here again if I am in the area."
United States
DAVID
$84 nightly
The price is $94
Dec 14 - Dec 15
Total with taxes and fees
Williamstown Motel
Exterior
Willows Motel Williamstown

Willows Motel Williamstown

2.0 star property
Williamstown
9.0 out of 10, Wonderful, (992)
"Warm welcome. Great location. Best fresh fruit breakfast ever."
United States
Melissa
$85 nightly
The price is $95
Dec 8 - Dec 9
Total with taxes and fees
Willows Motel Williamstown
Exterior
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2.0 star property
West Stockbridge
6.8 out of 10, (1002)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
$53 nightly
The price is $58
Jan 1 - Jan 2, 2026
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
Single Room | In-room safe, desk, free WiFi, bed sheets
Blue Vista Motor Lodge

Blue Vista Motor Lodge

2.0 star property
North Adams
9.8 out of 10, Exceptional, (195)
"The suite I booked was very spacious and clean. I enjoyed the hot tub and sauna, fire pits and the view. A very relaxing place to stay. "
United States
Jean
$179 nightly
The price is $189
Dec 8 - Dec 9
Total with taxes and fees
Blue Vista Motor Lodge
Seasonal outdoor pool
Sunset Inn

Sunset Inn

2.0 star property
Lee
7.6 out of 10, Good, (410)
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
$90 nightly
The price is $101
Dec 8 - Dec 9
Total with taxes and fees
Sunset Inn
Property grounds
Wagon Wheel Inn

Wagon Wheel Inn

2.0 star property
Lenox
7.0 out of 10, Good, (641)
"Beautiful area. Close to Mt. Greylock, Octobrr Mountain and Pleasant Valley Audubon."
United States
Benjamin
Wagon Wheel Inn
Front of property
Becket Motel

Becket Motel

2.5 star property
Becket
6.8 out of 10, (60)
"Comfortable stay "
United States
Paul
$122 nightly
The price is $137
Dec 14 - Dec 15
Total with taxes and fees
Becket Motel
Pool
Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown

2.0 star property
Williamstown
6.6 out of 10, (899)
"Great affordable place to stay while in the northern Berkshires."
United States
PAUL
$90 nightly
The price is $101
Dec 8 - Dec 9
Total with taxes and fees
Howard Johnson by Wyndham Williamstown
Standard Room, 1 King Bed | Desk, iron/ironing board, free cribs/infant beds, rollaway beds
Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington

2.0 star property
Lee
6.4 out of 10, (650)
"Great place. , good staff "
United States
ketul
$63 nightly
The price is $70
Dec 21 - Dec 22
Total with taxes and fees
Econo Lodge Lee - Great Barrington
Outdoor pool
Berkshire Travel Lodge

Berkshire Travel Lodge

2.5 star property
Austerlitz
5.4 out of 10, (459)
"The parking is right in front of the cabin the breakfast is made to order, very nice place "
United States
William
$76 nightly
The price is $85
Dec 8 - Dec 9
Total with taxes and fees
Berkshire Travel Lodge
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express

FairBridge Inn Express

2.5 star property
Pittsfield
5.4 out of 10, (810)
"Room spotless and staff helpful."
United States
William
$89 nightly
The price is $99
Dec 8 - Dec 9
Total with taxes and fees
FairBridge Inn Express
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 Cheshire Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"I enjoyed the holiday inn. I enjoyed the staff made me fell at home. I enjoyed the comfortable atmosphere and the room was nice and clean. I enjoyed the breakfast very much. The staff was very friendly. "
Brendan 1-night trip
Posted 3 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Find out more about Cheshire

Cheshire Motels information

Number of reviews
10,407
Accommodation
24 Motels
Lowest Price
$58
Highest Price
$189

Frequently asked questions

What is the nightly rate for a motel in Cheshire?
You can find a great deal from $58 on Cheshire motels with Expedia. Typically, prices are higher during popular times – like weekends and holidays – while staying midweek is often cheaper. To find the best nightly rates on Cheshire motels, try to be flexible with travel dates, and sort search results by price from low to high.
Is it better to stay in a Cheshire motel or hotel?
Motels and Hotels have different perks. When you stay at a motel, you're likely to find free parking and an outdoor pool. Staying overnight at a motel, can be handy when requiring easy road access. You'll often have access to your room from outside, and directly from the parking lot. Hotels generally have room access from inside the building. Motels are also often less expensive than hotels. The word "motel" was coined in 1925 by the owner of the Milestone Mo-Tel in San Luis Obispo, California.

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