Photo by Ed Gaffny

Search Hotel Resorts in Cheshire

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Browse Select Cheshire Resorts

Holiday Inn Club Vacations Oak 'n Spruce Resort
View from property
Holiday Inn Club Vacations Oak 'n Spruce Resort
2.0 star property
Holiday Inn Club Vacations Oak 'n Spruce Resort
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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.

Other property types in Cheshire

Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, 858 reviews
"Staff were so attentive, even at the late hour we checked in (10pm) the place had everything you need. Amazing views and amenities. Loved it"
The price is ₹13,271
per night
4 Jun - 5 Jun
Jiminy Peak Mountain Resort
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.

Cheshire Resorts information

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 Resorts
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Frequently asked questions

What is Cheshire like for a resort holiday?
You deserve a holiday, and a resort is just the place to find all the amenities and services you need for a relaxing time in Cheshire. One of the comfortable resorts in the area might be just what you’re looking for, whether you’re hoping for an amazing pool, shopping possibilities or activities for the youngsters.
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 temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Cheshire are January, April, March and February, with each month seeing an average of 20 cm 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) away from the heart of the city. You can also search 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.

Cheshire Hotel Reviews
Expedia verified reviews

The Lenox Collection

The Lenox Collection

5/5 Excellent
"This was the best stay we have had in a hotel in a very long time. We were at The Constance for four nights. May 13th with checkout Friday morning, May 17, 2024. The building is very old, and it had a lot of charm and character. Comfortable front porch with plenty of seating, and tables and chairs for your use. There was also a quaint parlor with chairs, couches, fireplace, and piano to the right of the front desk where we spent a rainy afternoon catching up on our reading. The rooms were very accommodating with updated bathrooms, plenty of closet space, and Roku TV. Our bed was very comfortable with full size pillows. When speaking to the staff, it was like speaking with old friends. They are all personable and make you feel like this is your home. Breakfast at The Constance was excellent. No eggs, but they had everything else. Bagels, muffins, coffee, tea, juice, granola, fresh blueberries and Chobani Yogurt. Everything was there for you to enjoy, just like at home."
A verified traveller stayed at The Lenox Collection
Posted 2 days ago
The Lenox Collection