Photo by Tai Bui

Search Resorts in Cheshire

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Check prices for these dates

Next weekend
2 Jum. I - 4 Jum. I
In two weeks
9 Jum. I - 11 Jum. I
In one month
23 Jum. I - 25 Jum. I
In two months
20 Jum. II - 22 Jum. II

Compare 1 Resorts in Cheshire with updated reviews, rates, and availability.

Lakeview Cottage with Dock, Kayaks
Exterior

Lakeview Cottage with Dock, Kayaks

9.6 out of 10, Exceptional, (15)
"Great place to stay and a really great owner. Setting is outstanding and the cabins are very clean and well maintained. We will definitely go back!!"
Lakeview Cottage with Dock, Kayaks
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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Other property types in Cheshire

Quiet 2bd Townhome apt in the heart of Cheshire.
Fridge, microwave, oven, stovetop

Quiet 2bd Townhome apt in the heart of Cheshire.

10.0 out of 10, Exceptional, (1)
"Overall a positive experience. Property was clean and worked out really well for us as location was close to family we were visiting. We are from Florida, and it was cold in CT and the heat worked great so that was really good. Andrew was responsive to requests. Only criticism was in some of the set up. There are no dressers, so you need to stack your clothes on shelves in closet, which was not terrible. Also, the only mirror in the entire place was in the bathroom downstairs (bedrooms...
The price is SAR 409
SAR 718 total
includes taxes & fees
7 May - 8 May
Quiet 2bd Townhome apt in the heart of Cheshire.
New Haven Village Suites
Suite, Multiple Beds | Egyptian cotton sheets, premium bedding, pillowtop beds, desk

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (2025)
"Good stay. "
New Haven Village Suites
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Outdoor pool, a heated pool

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (128)
"having previously rented VRBO properties in Palm Springs, West Palm Beach & Ft. Lauderdale I can confirm this property is exceptional. The studio has 1st tier amenities, waterfront location & in addition the hosts provided most welcoming foods and snacks, an overall wonderful experienceJimBrooklyn, NY"
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
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.

Frequently asked questions

What can I expect from a resort vacation in Cheshire?
You deserve a getaway, and a resort is the ideal place to indulge in all the services and amenities you need for a relaxing stay in Cheshire. One of the comfortable resort hotels in the surrounding area might be just what you’re searching for, whether you’re hoping for great restaurants on site, shopping possibilities, or fun activities to try.
What's the best resort for my stay in Cheshire?
Our highest-rated resort near Cheshire: Lakeview Cottage with Dock, Kayaks - 21.7 mi (34.9 km) from Cheshire.
What can I do in Cheshire?
Discover the shopping possibilities at Maplecroft Plaza Shopping Center, or bring the kids to Barker Character, Comic and Cartoon Museum for some family fun. For more to see in the area, you can spend time at Cheshire Hollow Farm or Drazen Orchards.
What's the weather like in Cheshire?
The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 33°F. Average annual precipitation for Cheshire is 54 inches.
What's the best way to get to and around Cheshire?
Fly into Oxford, CT (OXC-Waterbury - Oxford), which is located 12 mi (19.3 km) from the city center. You can also search for flights into New Haven, CT (HVN-Tweed - New Haven Regional), which is 16.5 mi (26.6 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.