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Best Resorts in Cheshire

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Jul 18 - Jul 20
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Jul 25 - Jul 27
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Aug 8 - Aug 10
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Sep 5 - Sep 7

Resorts in Cheshire

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Recommended hotels in Cheshire

Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (50)
"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!! "
$236 nightly
The price is $250
Aug 7 - Aug 8
Total includes taxes and fees
Harbour House Inn
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (103)
"Great Place to stay in Small town"
$138 nightly
The price is $150
Jul 30 - Jul 31
Total includes taxes and fees
Blooming Inn
2.5mi from the lake! Fire pit, arcade, yard games!
Fridge, microwave, oven, stovetop

2.5mi from the lake! Fire pit, arcade, yard games!

10.0 out of 10, Exceptional, (12)
"This place is immaculate and the host is responsive. We stayed here to ski in Mount snow which is about 25 minutes drive. We arrived later in the evening and the place was warm and cozy. "
$564 nightly
The price is $632
Aug 6 - Aug 7
Total includes taxes and fees
2.5mi from the lake! Fire pit, arcade, yard games!
UU Rowe Camp and Conference Center
Front of property

UU Rowe Camp and Conference Center

2.0 star property
UU Rowe Camp and Conference Center
Bear Creek Cabin
Exterior

Bear Creek Cabin

10.0 out of 10, Exceptional, (32)
"Enjoyed our stay"
$536 nightly
The price is $599
Jul 20 - Jul 21
Total includes taxes and fees
Bear Creek Cabin
Becket Motel
Front of property

Becket Motel

2.5 star property
6.6 out of 10, (58)
"Comfortable stay "
$120 nightly
The price is $135
Jul 28 - Jul 29
Total includes taxes and fees
Becket Motel
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Outdoor dining

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

$372 nightly
The price is $416
Jul 28 - Jul 29
Total includes taxes and fees
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Hummingbird Haven is a Berkshires retreat surrounded by nature and local charm.
Property grounds

Hummingbird Haven is a Berkshires retreat surrounded by nature and local charm.

10.0 out of 10, Exceptional, (3)
"This property was amazing! Very clean and spacious, perfect location for a nice peaceful getaway. Kendra was very communicative and made sure our stay was comfortable. 10/10 highly recommend you to stay here. "
$493 nightly
The price is $551
Jul 16 - Jul 17
Total includes taxes and fees
Hummingbird Haven is a Berkshires retreat surrounded by nature and local charm.
Blue Vista Motor Lodge
Single Room | 1 bedroom, in-room safe, desk, free WiFi

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (175)
"Lovely stay!"
$210 nightly
The price is $222
Jul 14 - Jul 15
Total includes taxes and fees
Blue Vista Motor Lodge
Florida Mountain Log Cabin!
Living area

Florida Mountain Log Cabin!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Place was super clean. Beds were comfortable. Location was great."
$420 nightly
The price is $444
Jul 14 - Jul 15
Total includes taxes and fees
Florida Mountain Log Cabin!
The Trail in Adams - Berkshires’ Art Hotel
Terrace/patio

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (130)
"Stayed only one night Very cosy, quiet place "
$176 nightly
The price is $197
Jul 15 - Jul 16
Total includes taxes and fees
The Trail in Adams - Berkshires’ Art Hotel
Park Street Penthouse Apartment
Game room

Park Street Penthouse Apartment

9.8 out of 10, Exceptional, (6)
"We stayed in this beautiful penthouse for an overnight get away- we both walked in and were just in love. The high ceilings and tons of windows made it so open feeling. Stunning place!"
$223 nightly
The price is $249
Jul 14 - Jul 15
Total includes taxes and fees
Park Street Penthouse Apartment
The Revival House
Romantic Room, 1 King Bed (Room 4) | 1 bedroom, desk, iron/ironing board, free WiFi

The Revival House

3.0 star property
9.6 out of 10, Exceptional, (4)
"The Revival House was charming and quiet. It had everything we needed for our short stay. It's only a 6 minute drive to the Bellows Pipe Trail/Mount Greylock, which was a huge plus for us. Wishing all the best for this newly opened hotel!"
$180 nightly
The price is $201
Jul 14 - Jul 15
Total includes taxes and fees
The Revival House
Hotel Downstreet, Ascend Hotel Collection
Hypo-allergenic bedding, laptop workspace, blackout drapes

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1001)
"Fantastic place"
$144 nightly
The price is $160
Aug 12 - Aug 13
Total includes taxes and fees
Hotel Downstreet, Ascend Hotel Collection
The Porches Inn at Mass MoCA
Exterior

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (395)
"Beautiful and peaceful property. Perfect for our last minute mother daughter get away. The staff was friendly and helpful. "
$240 nightly
The price is $268
Aug 12 - Aug 13
Total includes taxes and fees
The Porches Inn at Mass MoCA
Pilgrim Inn
Lobby

Pilgrim Inn

2.5 star property
5.8 out of 10, (309)
"Great location but no staff at check-in or checkout!"
$74 nightly
The price is $83
Aug 3 - Aug 4
Total includes taxes and fees
Pilgrim Inn
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1006)
"Friendly staff, easy parking"
$127 nightly
The price is $141
Jul 28 - Jul 29
Total includes taxes and fees
Quality Inn
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (389)
"No frills but it was a great stay!"
$105 nightly
The price is $118
Aug 11 - Aug 12
Total includes taxes and fees
Sunset Inn
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (740)
"A total dump !"
$69 nightly
The price is $78
Jul 14 - Jul 15
Total includes taxes and fees
FairBridge Inn Express
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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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. Enjoy the sauna, fitness center, and terrace.
What can I do in Cheshire?
Mount Greylock State Reservation and St Mary's of the Assumption Church are a few of the interesting sights to visit. In the area, other attractions include Mount Greylock State Reservation Visitor Center and Mount Greylock.
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.