A lake surrounded by autumn-colored trees and hills.

Cheshire Condominium Resorts to Rent

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28
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
$226 nightly
The price is $239
Dec 1 - Dec 2
Total with taxes and fees
Harbour House Inn
A hotel room with a bed, two bedside lamps, a chair, a dresser, a mirror, and a painting on the wall.

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 7 - Dec 8
Total with taxes and fees
Rodeway Inn
A patio area with outdoor furniture, a fire pit, and potted plants.

3. 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
$89 nightly
The price is $97
Nov 9 - Nov 10
Total with taxes and fees
The Springs Motel
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
$79 nightly
The price is $88
Nov 8 - Nov 9
Total with taxes and fees
FairBridge Inn Express
A blue wooden deck with white picket railings, surrounded by a well-maintained lawn and colorful autumn foliage.

5. Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (367 reviews)
"Excellent service, excellent stay."
United States
Ahmet
$80 nightly
The price is $89
Nov 8 - Nov 9
Total with taxes and fees
Williamstown Motel
A hotel room with a large bed, two bedside tables with lamps, a desk with a chair, and a small window.

6. Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (959 reviews)
"Room was very clean. Tastefully decorated. Beds were comfortable. Would stay there next time we go to Williamstown,Mass."
United States
Barbara
$100 nightly
The price is $112
Nov 26 - Nov 27
Total with taxes and fees
Howard Johnson by Wyndham Williamstown
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, (981 reviews)
"Very nice hotel"
United States
Philip
$119 nightly
The price is $133
Nov 29 - Nov 30
Total with taxes and fees
Hotel On North
A patio area with wooden chairs and tables, surrounded by dense greenery and trees.

8. 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
$89 nightly
The price is $99
Nov 8 - Nov 9
Total with taxes and fees
Willows Motel Williamstown
A kitchen with a countertop, a refrigerator, and a window.

9. 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
$69 nightly
The price is $77
Dec 1 - Dec 2
Total with taxes and fees
The Villager Motel
Indoor pool

10. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,835 reviews)
"Great resort, great location very spacious."
United States
Marcos
$122 nightly
The price is $136
Dec 8 - Dec 9
Total with taxes and fees
Vacation Village in the Berkshires
A fenced outdoor area with a pool, lounge chairs, and umbrellas.

11. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (941 reviews)
"It was an ok place to stay for 2 nights"
United States
cheryl
$80 nightly
The price is $89
Dec 8 - Dec 9
Total with taxes and fees
Berkshire Inn
An outdoor seating area with Adirondack chairs and potted plants.

12. 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
$79 nightly
The price is $88
Nov 16 - Nov 17
Total with taxes and fees
Cozy Corner Motel
A hotel room with a bed, a sofa, a TV, and a desk with a lamp.

13. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
9.0 out of 10, Wonderful, (1,003 reviews)
"Had a great time at this wonderful hotel."
United States
marwan
$119 nightly
The price is $133
Nov 22 - Nov 23
Total with taxes and fees
Hotel Downstreet, an Ascend Collection Hotel
A covered porch with white furniture and green chairs, surrounded by lush greenery.

14. 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
$99 nightly
The price is $111
Nov 8 - Nov 9
Total with taxes and fees
1896 House Country Inn & Motels
A garden with a swing set, a blue chair, and a flower bed.

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 8 - Nov 9
Total with taxes and fees
Maple Terrace Motel
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

16. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (435 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
$89 nightly
The price is $100
Nov 26 - Nov 27
Total with taxes and fees
The Central Downtown Inn & Suites
An indoor swimming pool with clear water, tiled floors, and a blue wall.

17. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (257 reviews)
"The room was clean and well kept, breakfast was amazing!"
United States
Ruth
$103 nightly
The price is $115
Dec 6 - Dec 7
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A living room with a fireplace, two sofas, and four black side tables.

18. The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (44 reviews)
"Room 6 was much larger than expected! We arrived after hours and it was very easy to find our room."
United States
Katrina
$150 nightly
The price is $168
Nov 12 - Nov 13
Total with taxes and fees
The Revival House
A wooden cabin with a porch and steps leading to a door, surrounded by snow.

19. Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.4 out of 10, Very good, (1,003 reviews)
"Nice resort and friendly staff."
United States
Olga
$130 nightly
The price is $145
Nov 17 - Nov 18
Total with taxes and fees
Jiminy Peak Mountain Resort
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

20. 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
$93 nightly
The price is $104
Dec 1 - Dec 2
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Gorgeous setting, comfortable beds and luxurious accommodations."
Carol 1-night trip
Posted 8 hours ago
Vacation Village in the Berkshires

Find out more about Cheshire

Cheshire Condo Resorts information

Number of reviews
1,930
Accommodation
0 Condo Resorts
Lowest Price
$72
Highest Price
$239

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