A lake surrounded by autumn-colored trees and hills.

Search Cheshire Villa Rentals from CA $102

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7
No exact matches found, but these alternatives could be just right

Recommended hotels in Cheshire

A large, two-story house with a front porch and a well-maintained garden with various flowers and shrubs.

1. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.8 out of 10, Exceptional, (58 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is CA $298
CA $314 total
includes taxes & fees
Dec 1 - Dec 2
Harbour House Inn
A patio area with outdoor furniture, a fire pit, and potted plants.

2. The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.2 out of 10, Wonderful, (123 reviews)
"Loved the vibe!"
United States
Elizabeth
The price is CA $133
CA $146 total
includes taxes & fees
Nov 16 - Nov 17
The Springs Motel
A single-story building with a porch, a chimney, and a satellite dish.

3. Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (285 reviews)
"The motel was clean and somewhat updated. Check in and check out was easy. Across the street was a yummy pizzeria."
United States
Joann
The price is CA $91
CA $102 total
includes taxes & fees
Dec 8 - Dec 9
Rodeway Inn
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

4. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (935 reviews)
"Friendly staff"
United States
William
The price is CA $100
CA $112 total
includes taxes & fees
Nov 10 - Nov 11
FairBridge Inn Express
A small, single-story building with a green roof and a white exterior. There are two large trees in front of the building, each with a flower pot on top. The surrounding area has grass, a few pumpkins, and a small garden with red flowers.

5. Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (368 reviews)
"Yes no frills but good for an economic stay. Great coffee at The Coffee Shop Williamstown nearby"
United States
Grantley
The price is CA $118
CA $132 total
includes taxes & fees
Nov 16 - Nov 17
Williamstown Motel
A multi-story hotel with a classic facade, large windows, and a prominent entrance.

6. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (981 reviews)
"Very nice hotel"
United States
Philip
The price is CA $164
CA $183 total
includes taxes & fees
Nov 29 - Nov 30
Hotel On North
A white two-story building with a porch, labeled as a motel.

7. Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (1,002 reviews)
"Outstanding bed and breakfast in Williamstown, walking distance to the college, and also close to Mass MOCA. Will be staying there again. The fresh fruit was absolutely outstanding."
United States
Anuj
The price is CA $119
CA $133 total
includes taxes & fees
Nov 10 - Nov 11
Willows Motel Williamstown
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

8. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,837 reviews)
"Gorgeous setting, comfortable beds and luxurious accommodations."
United States
Carol
The price is CA $114
CA $142 total
includes taxes & fees
Nov 10 - Nov 11
Vacation Village in the Berkshires
A motel with a parking lot, a swimming pool, and outdoor seating.

9. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (942 reviews)
"It was an ok place to stay for 2 nights"
United States
cheryl
The price is CA $117
CA $130 total
includes taxes & fees
Dec 9 - Dec 10
Berkshire Inn
A covered porch with benches and potted plants, overlooking a parking area with cars and a view of hills.

10. Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (966 reviews)
"Very clean and welcoming room. Staff man was very helpful and conscientious"
United States
Frank
The price is CA $106
CA $125 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Corner Motel
A motel named 'The Villager Motel' with a 'VACANCY' sign, a picnic table, and a red planter on the lawn.

11. The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (839 reviews)
"Everything was so clean, staff at the front desk were kind, will definitely be back if we stay in the area again!"
United States
Khileigh
The price is CA $97
CA $109 total
includes taxes & fees
Dec 1 - Dec 2
The Villager Motel
A building with a covered parking area and a grassy front yard.

12. Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (962 reviews)
"Needed a home away from home when a renovation turned into a nightmare. The family who runs this place are lovely and kind, the hotel is clean if a bit older. Solid choice in the area. Will let friends and family know if they are coming, simple clean hotel."
United States
Kate
The price is CA $141
CA $158 total
includes taxes & fees
Nov 26 - Nov 27
Howard Johnson by Wyndham Williamstown
A two-story building with a symmetrical facade, large columns, and a central entrance.

13. The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (46 reviews)
"Room 6 was much larger than expected! We arrived after hours and it was very easy to find our room."
United States
Katrina
The price is CA $212
CA $237 total
includes taxes & fees
Nov 10 - Nov 11
The Revival House
A house with a porch, snow-covered ground, and a Christmas tree with lights.

14. Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (648 reviews)
"Perfect charming little hotel The couple at the front was very nice and helpful"
United States
yeraldine
The price is CA $140
CA $156 total
includes taxes & fees
Nov 10 - Nov 11
Maple Terrace Motel
A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.

15. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (436 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
The price is CA $137
CA $153 total
includes taxes & fees
Nov 11 - Nov 12
The Central Downtown Inn & Suites
A modern hotel building with the name "Hotel Downtown" on the facade.

16. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
9.0 out of 10, Wonderful, (1,006 reviews)
"Had a great time at this wonderful hotel."
United States
marwan
The price is CA $168
CA $188 total
includes taxes & fees
Nov 22 - Nov 23
Hotel Downstreet, an Ascend Collection Hotel
Exterior

17. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,265 reviews)
"Excellent stay!!!!"
United States
Susan J
The price is CA $108
CA $153 total
includes taxes & fees
Dec 6 - Dec 7
Berkshire Mountain Lodge
A white two-story house with a sloped roof, large windows, and a small porch.

18. 1896 House Country Inn & Motels

1896 House Country Inn & Motels
2.5 star property
Williamstown
6.8 out of 10, (459 reviews)
"Decent"
United States
Maryann
The price is CA $122
CA $136 total
includes taxes & fees
Nov 10 - Nov 11
1896 House Country Inn & Motels
A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

19. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.4 out of 10, Very good, (1,002 reviews)
"Room was spacious and clean"
United States
James
The price is CA $132
CA $148 total
includes taxes & fees
Dec 1 - Dec 2
Best Western Plus Berkshire Hills Inn & Suites
A covered balcony with a table and two white wire chairs, a bowl of fruit, and a glass of juice.

20. The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.2 out of 10, Wonderful, (159 reviews)
"Fun decor, friendly staff, great complimentary breakfast, directly on bike path."
United States
Susan
The price is CA $241
CA $269 total
includes taxes & fees
Dec 10 - Dec 11
The Trail in Adams - Berkshires’ Art Hotel
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"The Red lion Inn is a unique historical stay. The hotel is charming with so many historical items to look at every turn. There are plenty of cute shops and great hiking trails right down the road."
Jennifer 1-night trip
Posted 5 hours ago
The Red Lion Inn

Find out more about Cheshire

Cheshire Villas information

Number of reviews
3,331
Accommodation
3 Villas
Lowest Price
CA $102
Highest Price
CA $314

Frequently asked questions

Why book your villa in Cheshire with Expedia?
Booking a villa in Cheshire is as easy as entering your travel dates and selecting an option that has what you need. Looking for something budget friendly or upmarket, or a stay that also includes a kitchenette? Use Expedia's search filters to narrow your results and find the perfect pad.
How can I find cheap villas in Cheshire?
With Expedia's filter tool, reserving cheap villas in Cheshire has never been easier. To discover accommodations that are easy on the wallet, narrow your search results by budget, amenities and star rating.
What is there to do near my villa in Cheshire?
If you'd like to see the sights of Cheshire, check out St Mary's of the Assumption Church. It's popular with locals and tourists alike.

Explore a world of travel with Expedia