A lake surrounded by autumn-colored trees and hills.

Find Cheshire motels from $68

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Aug 21 - Aug 23
In two weeks
Aug 28 - Aug 30
In one month
Sep 11 - Sep 13
In two months
Oct 9 - Oct 11

Our top choices for Cheshire motels

Desk, iron/ironing board, WiFi (free), bed sheets

1. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (868 reviews)
"Some of the furniture and rugs show age. The bed was comfortable and the staff was always available to help!"
United States
DAVID
$61 nightly
The price is $68
Aug 27 - Aug 28
Total with taxes and fees
FairBridge Inn Express
Courtyard

2. The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.2 out of 10, Wonderful, (111 reviews)
"We enjoyed our stay. Staff was nice and the motel is set between several different towns to explore. We plan to stay again soon!"
United States
Shakeila
$156 nightly
The price is $172
Aug 23 - Aug 24
Total with taxes and fees
The Springs Motel
Desk, iron/ironing board, WiFi (free), bed sheets

3. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (906 reviews)
"Very clean and updated simple motel."
United States
christopher
$90 nightly
The price is $101
Aug 13 - Aug 14
Total with taxes and fees
Berkshire Inn
Gazebo

4. Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (937 reviews)
"Loved this place"
United States
Jeremy
$93 nightly
The price is $104
Sep 9 - Sep 10
Total with taxes and fees
Cozy Corner Motel
Property grounds

5. Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,000 reviews)
"This was an excellent stay in the Berkshires!"
United States
Richard
$109 nightly
The price is $122
Aug 16 - Aug 17
Total with taxes and fees
Willows Motel Williamstown
View from property

6. Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (337 reviews)
"Very clean room and friendly staff. Lots of great restaurants close by."
United States
Robert
$102 nightly
The price is $114
Aug 13 - Aug 14
Total with taxes and fees
Williamstown Motel
In-room safe, desk, laptop workspace, iron/ironing board

7. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (893 reviews)
"Great place"
United States
Luciane
$79 nightly
The price is $88
Aug 31 - Sep 1
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Property grounds

8. Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (630 reviews)
"Great spot with everything we needed"
United States
Christine
$125 nightly
The price is $140
Sep 8 - Sep 9
Total with taxes and fees
Maple Terrace Motel
Reception

9. The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (811 reviews)
"We stayed one night in July. Easy check-in and clean room."
United States
Rebecca
$89 nightly
The price is $99
Sep 1 - Sep 2
Total with taxes and fees
The Villager Motel
Children's activities

10. Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,006 reviews)
"Very comfortable. Will stay there again"
United States
Peter
$69 nightly
The price is $76
Aug 19 - Aug 20
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
Exterior

11. Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (224 reviews)
"Very nice place to stay with captivating view"
United States
Frederic
$246 nightly
The price is $260
Aug 17 - Aug 18
Total with taxes and fees
Blue Vista Motor Lodge
Outdoor pool

12. Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (499 reviews)
"Perfect as I was just needing a place to stay overnight."
United States
Kris
$67 nightly
The price is $76
Aug 25 - Aug 26
Total with taxes and fees
Berkshire Travel Lodge
Seasonal outdoor pool

13. Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (432 reviews)
"It was a great stay, close to many amenities. The room was clean, with a comfortable bed."
Canada
Kevin
$96 nightly
The price is $107
Sep 2 - Sep 3
Total with taxes and fees
Sunset Inn
In-room dining

14. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (687 reviews)
"The outside of the hotel needed a lot of upkeep like paint and the stairs were particularly ugly. The inside was clean and neat and the people were wonderful. Great for a budget hotel."
United States
Lynne
$67 nightly
The price is $75
Sep 7 - Sep 8
Total with taxes and fees
Econo Lodge Lee - Great Barrington
Lake view

15. Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.6 out of 10, Exceptional, (11 reviews)
"The air conditioning was effective and the view of the lake was peaceful and beautiful."
United States
Rita
$155 nightly
The price is $173
Aug 31 - Sep 1
Total with taxes and fees
Berkshire Lake Lodge
Front of property

16. Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (62 reviews)
"Comfortable stay "
United States
Paul
$131 nightly
The price is $146
Aug 30 - Aug 31
Total with taxes and fees
Becket Motel
Mountain view

17. Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (930 reviews)
"Great place"
United States
Donna
$100 nightly
The price is $112
Aug 13 - Aug 14
Total with taxes and fees
Howard Johnson by Wyndham Williamstown
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cheshire Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"Pool and staff was great"
peter 2-night trip
Posted 9 hours ago
Vacation Village in the Berkshires

Find out more about Cheshire

Cheshire Motels information

Number of reviews
6,620
Accommodation
26 Motels
Lowest Price
$68
Highest Price
$260

Frequently asked questions

What is the nightly rate for a motel in Cheshire?
You can find a great deal from $68 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.

Explore a world of travel with Expedia