A lake surrounded by autumn-colored trees and hills.

Cheshire Castle Hotels

Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10
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
$254 nightly
The price is $268
Nov 30 - Dec 1
Total with taxes and fees
Harbour House Inn
A single-story building with a porch, a chimney, and a satellite dish.

2. 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
$65 nightly
The price is $72
Dec 13 - Dec 14
Total with taxes and fees
Rodeway Inn
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

3. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (936 reviews)
"Friendly staff"
United States
William
$79 nightly
The price is $88
Nov 15 - Nov 16
Total with taxes and fees
FairBridge Inn Express
A patio area with outdoor furniture, a fire pit, and potted plants.

4. The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.0 out of 10, Wonderful, (124 reviews)
"Loved the vibe!"
United States
Elizabeth
$106 nightly
The price is $116
Dec 10 - Dec 11
Total with taxes and fees
The Springs Motel
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, (369 reviews)
"Yes no frills but good for an economic stay. Great coffee at The Coffee Shop Williamstown nearby"
United States
Grantley
$81 nightly
The price is $90
Nov 29 - Nov 30
Total with taxes and fees
Williamstown Motel
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

6. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,841 reviews)
"Gorgeous setting, comfortable beds and luxurious accommodations."
United States
Carol
$108 nightly
The price is $121
Nov 17 - Nov 18
Total with taxes and fees
Vacation Village in the Berkshires
A multi-story hotel with a classic facade, large windows, and a prominent entrance.

7. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (984 reviews)
"Staff very pleasant and accommodating."
United States
Rosemarie
$112 nightly
The price is $125
Nov 29 - Nov 30
Total with taxes and fees
Hotel On North
A motel with multiple rooms, a parking area, and a large tree in the foreground.

8. Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (964 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
$100 nightly
The price is $112
Nov 26 - Nov 27
Total with taxes and fees
Howard Johnson by Wyndham Williamstown
A white two-story building with a porch, labeled as a motel.

9. Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (1,000 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
$89 nightly
The price is $99
Nov 15 - Nov 16
Total with taxes and fees
Willows Motel Williamstown
A motel with a two-story structure, a covered parking area, and a well-maintained lawn with a flower bed.

10. Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (969 reviews)
"Very friendly and helpful"
United States
Adrienne
$79 nightly
The price is $88
Nov 16 - Nov 17
Total with taxes and fees
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)
"Friendly staff, quiet location set back from the road, this is our go-to place in Williamstown."
United States
Miguel
$69 nightly
The price is $77
Dec 1 - Dec 2
Total with taxes and fees
The Villager Motel
A motel with a parking lot, a swimming pool, and outdoor seating.

12. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (944 reviews)
"It was an ok place to stay for 2 nights"
United States
cheryl
$81 nightly
The price is $90
Dec 13 - Dec 14
Total with taxes and fees
Berkshire Inn
A two-story building with a central entrance, a covered porch, and a small balcony.

13. 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
$97 nightly
The price is $109
Nov 17 - Nov 18
Total with taxes and fees
The Central Downtown Inn & Suites
A modern hotel building with the name "Hotel Downtown" on the facade.

14. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
9.0 out of 10, Wonderful, (1,000 reviews)
"Had a great time at this wonderful hotel."
United States
marwan
$119 nightly
The price is $133
Nov 26 - Nov 27
Total with taxes and fees
Hotel Downstreet, an Ascend Collection Hotel
A house with a porch, snow-covered ground, and a Christmas tree with lights.

15. 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
$99 nightly
The price is $111
Nov 15 - Nov 16
Total with taxes and fees
Maple Terrace Motel
A wooden cabin with a porch and steps leading to a door, surrounded by snow.

16. Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.4 out of 10, Very good, (1,004 reviews)
"Nice resort and friendly staff."
United States
Olga
$130 nightly
The price is $145
Nov 20 - Nov 21
Total with taxes and fees
Jiminy Peak Mountain Resort
A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

17. 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, (1,003 reviews)
"Room was spacious and clean"
United States
James
$93 nightly
The price is $104
Dec 1 - Dec 2
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Exterior

18. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,268 reviews)
"Excellent stay!!!!"
United States
Susan J
$106 nightly
The price is $118
Dec 13 - Dec 14
Total with taxes and fees
Berkshire Mountain Lodge
A white two-story house with a sloped roof, large windows, and a small porch.

19. 1896 House Country Inn & Motels

1896 House Country Inn & Motels
2.5 star property
Williamstown
6.8 out of 10, (460 reviews)
"Decent"
United States
Maryann
$99 nightly
The price is $111
Nov 15 - Nov 16
Total with taxes and fees
1896 House Country Inn & Motels
A two-story building with a symmetrical facade, large columns, and a central entrance.

20. The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (46 reviews)
"Nice historic, Inn like feeling. Comfy rooms, easy breakfast until 1pm!! Staff responsive via SMS almost 24/7"
United States
Ruby
$138 nightly
The price is $154
Nov 29 - Nov 30
Total with taxes and fees
The Revival House
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"clean room - pleasant staff"
Tina 1-night trip
Posted 3 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Cheshire

Cheshire Castles information

Number of reviews
1,369
Accommodation
0 Castles
Lowest Price
$72
Highest Price
$268

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