Romantic Hotels in Chestertown, NY

Start date: Check-in selected.
To Date
End date: Check-out

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Top Chestertown Romantic Getaways & Hotels

The Fern Lodge

The Fern Lodge

3.5 out of 5
46 Fiddlehead Bay Rd., Chestertown, NY
$587 nightly
The price is $652 total per night
$652 total
Oct 12 - Oct 13
Total with taxes and fees
Private hot tubs, in-room massages, and a garden await couples visiting this romantic bed & breakfast. The property also offers jetted tubs, in-room fireplaces, ...
Friends Lake Inn

Friends Lake Inn

4 out of 5
963 Friends Lake Rd, Chestertown, NY
$235 nightly
The price is $261 total per night
$261 total
Sep 28 - Sep 29
Total with taxes and fees
A garden, a lobby fireplace, and champagne service await visiting couples at this romantic hotel. The property also offers romance packages and private ...
Don't see what you're looking for?
See all available properties in Chestertown
View all properties
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.

Chestertown hotels essential information

Accommodation
1,545 hotels
Lowest Price
$261
Highest Price
$652
Popular hotels
Friends Lake Inn, The Fern Lodge

Recent Chestertown hotel reviews by fellow wanderers

The Queensbury Hotel

The Queensbury Hotel

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"nicely decorated and meticulously maintained. Beautiful hotel with good rates."
A verified traveler stayed at The Queensbury Hotel
The Queensbury Hotel