Chester, CT Resorts

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Compare Resorts in Chester with updated reviews, rates, and availability.

Other property types in Chester

"The Villa was beautiful and immaculately clean. The host, Taylor, was very easy to communicate with. "

SAR 1,214 total

includes taxes & fees

30 Jun - 1 Jul

"This cottage is so adorable and just a short walk to the beach and a local convenience store. This makes it easy to park the car and just walk to get coffee and such. We stayed in October so not much open this time of year, but we were in the area for a family wedding so not much time to hang out anyway. This was the first time I've rented on Vrbo, so I wasn't sure what to expect as have read a lot about obnoxious owners with tons of rules, but Brett is super-chill with only a couple of things...

Montville Vacation Rental | 1BR | 1BA | 625 Sq Ft | Stairs Required to Enter

"Enjoyed our 2 days of quiet and relaxation, especially from the deck with its lovely view!"

Frequently asked questions

What can I expect from a resort vacation in Chester?

You deserve to get away, and a resort is the ideal place to treat yourself to the services and amenities you need for a relaxing trip to Chester. One of the comfortable resort hotels in the surrounding area might be just what you’re searching for, whether you’re hoping for a luxurious suite, blissful spa treatments, or activities for the kids.

What can I do in Chester?

Experience the local theater scene at Norma Terris Theater, or bring the kids to Essex Steam Train for some family fun. A few other attractions you may want to see are Connecticut River and Cockaponset State Forest.

What's the weather like in Chester?

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 35°F. Average annual precipitation for Chester is 54 inches.

What's the best way to get to and around Chester?

Fly into New Haven, CT (HVN-Tweed - New Haven Regional), which is located 23.1 mi (37.2 km) from the city center. You can also search for flights into New London, CT (GON-Groton - New London), which is 23.1 mi (37.2 km) away. If you’d like to venture out around the area, you may want a rental car for your journey.