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Best Resorts in Cheshire

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Resorts in Cheshire

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Recommended hotels in Cheshire

Harbour House Inn
3.5 star property
9.4 out of 10, Exceptional, (52)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
United States
Lorie
$252 nightly
The price is $267
Oct 27 - Oct 28
Total with taxes and fees
Harbour House Inn
Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
8.6 out of 10, Excellent, (1020)
"Good breakfast; pleasant staff on duty 24/7; convenient location."
United States
Dan and Alice
$102 nightly
The price is $114
Nov 2 - Nov 3
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
The Springs Motel
2.0 star property
9.2 out of 10, Wonderful, (83)
"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
$94 nightly
The price is $104
Oct 28 - Oct 29
Total with taxes and fees
The Springs Motel
Quality Inn
2.5 star property
8.4 out of 10, Very Good, (1001)
"Staff was very helpful - easy location - clean rooms!"
United States
Karen
$93 nightly
The price is $104
Nov 9 - Nov 10
Total with taxes and fees
Quality Inn
Blooming Inn
3.0 star property
9.2 out of 10, Wonderful, (115)
"Lovely Inn and very responsive and approachable staff. "
United States
Jesse
$139 nightly
The price is $150
Nov 2 - Nov 3
Total with taxes and fees
Blooming Inn
Howard Johnson by Wyndham Lenox
2.0 star property
7.6 out of 10, Good, (815)
"Staff was very friendly and helpful."
United States
Pamela
$79 nightly
The price is $88
Oct 27 - Oct 28
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Element Lenox Berkshires
3.0 star property
9.4 out of 10, Exceptional, (6)
"New hotel very nice"
United States
joel
$135 nightly
The price is $151
Nov 2 - Nov 3
Total with taxes and fees
Element Lenox Berkshires
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very Good, (919)
"Friendly staff and clean rooms. Loved the onsite restaurant & bar."
United States
Carmen
$103 nightly
The price is $115
Nov 2 - Nov 3
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Villager Motel
2.0 star property
8.8 out of 10, Excellent, (750)
"It's very good for stay over"
United States
Frances
$75 nightly
The price is $84
Nov 16 - Nov 17
Total with taxes and fees
The Villager Motel
The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
9.0 out of 10, Wonderful, (1006)
"Great Indian restaurant in the hotel!"
United States
Chris
$106 nightly
The price is $119
Nov 2 - Nov 3
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
In town, newly remodeled studio with private balcony
10.0 out of 10, Exceptional, (119)
"Beautiful, clean, perfect for a relaxing getaway! The little porch was my favorite place to read, have a glass of wine, and in the morning enjoy my coffee. The property was walking distance to everything I needed! "
United States
Caroline L.
$131 nightly
The price is $146
Nov 3 - Nov 4
Total with taxes and fees
In town, newly remodeled studio with private balcony
Hampton Inn & Suites Berkshires-Lenox
2.5 star property
9.2 out of 10, Wonderful, (1005)
"The staff is very friendly and helpful "
United States
karin
$111 nightly
The price is $124
Nov 9 - Nov 10
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (430)
"Very casual and easy check in and out; lovely and substantial breakfast"
United States
Jamie
$103 nightly
The price is $114
Nov 4 - Nov 5
Total with taxes and fees
Shaker Mill Inn
Sunset Inn
2.0 star property
7.6 out of 10, Good, (408)
"That can be reserved at any time"
United States
Felicita
$84 nightly
The price is $94
Nov 24 - Nov 25
Total with taxes and fees
Sunset Inn
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (786)
"Clean room, great location. Restaurant phenomenal "
United States
Mary
$98 nightly
The price is $110
Nov 11 - Nov 12
Total with taxes and fees
Hotel On North
Cozy Corner Motel
2.0 star property
9.2 out of 10, Wonderful, (877)
"Very nice staff, nice breakfast"
United States
Kerri
$79 nightly
The price is $88
Nov 2 - Nov 3
Total with taxes and fees
Cozy Corner Motel
Williamstown Motel
2.0 star property
9.4 out of 10, Exceptional, (307)
"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
$91 nightly
The price is $102
Oct 27 - Oct 28
Total with taxes and fees
Williamstown Motel
Howard Johnson by Wyndham Williamstown
2.0 star property
6.6 out of 10, (894)
"Great affordable place to stay while in the northern Berkshires."
United States
PAUL
$120 nightly
The price is $134
Oct 27 - Oct 28
Total with taxes and fees
Howard Johnson by Wyndham Williamstown
Berkshire Inn
2.0 star property
7.8 out of 10, Good, (835)
"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
$77 nightly
The price is $87
Nov 24 - Nov 25
Total with taxes and fees
Berkshire Inn
Willows Motel Williamstown
2.0 star property
9.0 out of 10, Wonderful, (971)
"Very friendly staff and fresh fruit at breakfast!"
United States
Justin
$99 nightly
The price is $111
Oct 27 - Oct 28
Total with taxes and fees
Willows Motel 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.
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Top Cheshire Hotel Reviews

Find out more about Cheshire

Cheshire Resorts information

Number of reviews
12,332
Accommodation
34 Resorts
Lowest Price
$84
Highest Price
$267

Frequently asked questions

What is Cheshire like for a resort vacation?
You deserve a vacation, and a resort is just the place to find all the amenities and services you need for a relaxing trip to Cheshire. One of the comfortable resorts in the area might be just what you're looking for, whether you're hoping for a luxurious suite, shopping possibilities, or fun activities to try.
What's the best resort for my stay in Cheshire?
Here's our top-rated resort near Cheshire: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 20.6 mi (33.2 km) from Cheshire. Access to a sauna, a fitness center, and a terrace.
What can I do in Cheshire?
Mount Greylock State Reservation, St Mary's of the Assumption Church, and Mount Greylock State Reservation Visitor Center are a few interesting places to visit nearby. In the area, other attractions include Mount Greylock and Brodie Mountain.
What's the weather like in Cheshire?
The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to get to and around Cheshire?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 11.5 mi (18.5 km) from the city center. Otherwise, look for flights into Hudson, NY (HCC-Columbia County), which is 33.6 mi (54 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.

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