Photo by Annette Babek

Find Romantic Hotels in Chester, CT

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Pick from 1 Chester Romantic Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

Stunning Artisan Waterfall Escape [Walk to Downtown]
A few steps away in the backyard you will find a waterfall (& two chairs now).

Stunning Artisan Waterfall Escape [Walk to Downtown]

10.0 out of 10, Exceptional, (42)
"It doesn’t get any better than this if you want to truly enjoy nature and the sweet town of Chester. The location, the accommodations, the thoughtfulness, and the ease of this home area unmatched. We cannot WAIT to return! "
Stunning Artisan Waterfall Escape [Walk to Downtown]
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

Searching for romantic hotels in Chester?
If you and your partner need a romantic vacation, we’ve got just the ticket. If you’d like to explore some of the area’s notable sights, you might make a stop by Cockaponset State Forest, Connecticut River, or Connecticut Valley Railroad State Park Trail. If you’d like to stay close to a certain attraction, you can sort properties by neighborhood or distance to top sights, so you’ll be able to see everything on your list.
When is the best time of year for a romantic getaway to Chester?
If you’re hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures 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 is there to do in Chester?
There’s nothing better than seeing a new destination with your sweetheart, so consider checking out all that Chester has to offer. Cockaponset State Forest, Connecticut River, and Connecticut Valley Railroad State Park Trail are worth a stop when you’re out and about.
What's the best way to get to Chester and around town during my romantic getaway?
This information about transportation options in Chester might help your romantic trip get off to a smooth start: Make your way to Chester with a flight to New Haven, CT (HVN-Tweed - New Haven Regional), which is the closest major airport located 23.1 mi (37.2 km) from the city center. If you’d like to venture out around the area, you may want to rent a car for your trip.