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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

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, (49)
"Nice place for a weekend away."
The price is SAR 886
SAR 936 total
includes taxes & fees
25 Jun - 26 Jun
Harbour House Inn
In town, newly remodeled studio with private balcony
Smart TV, Netflix, streaming services

In town, newly remodeled studio with private balcony

10.0 out of 10, Exceptional, (107)
"Great place. Quiet, clean and spacious - thank you so much "
The price is SAR 357
SAR 587 total
includes taxes & fees
1 Jul - 2 Jul
In town, newly remodeled studio with private balcony
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (97)
"Great Place to stay in Small town"
The price is SAR 331
SAR 516 total
includes taxes & fees
23 Jun - 24 Jun
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. "
The price is SAR 942
SAR 2,152 total
includes taxes & fees
8 Jul - 9 Jul
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
The price is SAR 559
SAR 591 total
includes taxes & fees
2 Jul - 3 Jul
UU Rowe Camp and Conference Center
Bear Creek Cabin
Exterior

Bear Creek Cabin

9.8 out of 10, Exceptional, (30)
"Enjoyed our stay"
The price is SAR 1,501
SAR 2,196 total
includes taxes & fees
22 Jun - 23 Jun
Bear Creek Cabin
Becket Motel
Front of property

Becket Motel

2.5 star property
6.6 out of 10, (55)
"Comfortable stay "
The price is SAR 359
SAR 526 total
includes taxes & fees
20 Jul - 21 Jul
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!

The price is SAR 507
SAR 1,367 total
includes taxes & fees
23 Jun - 24 Jun
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
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, (172)
"Lovely stay!"
The price is SAR 750
SAR 792 total
includes taxes & fees
22 Jun - 23 Jun
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."
The price is SAR 760
SAR 1,537 total
includes taxes & fees
22 Jun - 23 Jun
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, (129)
"Stayed only one night Very cosy, quiet place "
The price is SAR 652
SAR 728 total
includes taxes & fees
22 Jun - 23 Jun
The Trail in Adams - Berkshires’ Art Hotel
Park Street Penthouse Apartment
Game room

Park Street Penthouse Apartment

9.6 out of 10, Exceptional, (4)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
The price is SAR 456
SAR 941 total
includes taxes & fees
22 Jun - 23 Jun
Park Street Penthouse Apartment
Serene 2-bedroom apartment in North Adams.Plenty of off street parking.
Fridge, microwave, oven, stovetop

Serene 2-bedroom apartment in North Adams.Plenty of off street parking.

10.0 out of 10, Exceptional, (2)
"This apartment is roomy and fully appointed. Because of some physical issues we were unable to use the queen bed...it was too high. However, the twin beds were very comfy. The location is just right. So close to the Mohawk Trail, VT border and all the wonderful businesses that revolve around art. Our visits with family and friends were made even better because of our carefree accommodations! Thank you...SandyPeggi & Rick"
The price is SAR 507
SAR 880 total
includes taxes & fees
30 Jun - 1 Jul
Serene 2-bedroom apartment in North Adams.Plenty of off street parking.
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
The price is SAR 630
SAR 704 total
includes taxes & fees
22 Jun - 23 Jun
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, (1000)
"Staff super friendly, most comfortable beds imo I’ve slept in. I sleep better there then at my house."
The price is SAR 539
SAR 602 total
includes taxes & fees
20 Jul - 21 Jul
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, (390)
"Phenomenal room, staff and location! We loved The Porches!!"
The price is SAR 740
SAR 910 total
includes taxes & fees
23 Jun - 24 Jun
The Porches Inn at Mass MoCA
Pilgrim Inn
1 bedroom, individually decorated, individually furnished, desk

Pilgrim Inn

2.5 star property
5.8 out of 10, (308)
"Great location but no staff at check-in or checkout!"
The price is SAR 308
SAR 344 total
includes taxes & fees
23 Jun - 24 Jun
Pilgrim Inn
Deluxe Queen Room with 2 Queen Beds
1 bedroom, WiFi, bed sheets

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...
The price is SAR 447
SAR 583 total
includes taxes & fees
25 Jun - 26 Jun
Deluxe Queen Room with 2 Queen Beds
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1000)
"Friendly staff, easy parking"
The price is SAR 406
SAR 453 total
includes taxes & fees
7 Jul - 8 Jul
Quality Inn
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (381)
"The room was clean and perfect for our stay."
The price is SAR 342
SAR 382 total
includes taxes & fees
7 Jul - 8 Jul
Sunset Inn
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. Access to a sauna, a fitness center, and a 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.