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Find Romantic Hotels in Chestertown, NY

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Check availability on Chestertown Romantic Hotels

Tonight
2 Jul - 3 Jul
Tomorrow
3 Jul - 4 Jul
This weekend
4 Jul - 6 Jul
Next weekend
11 Jul - 13 Jul

Top Chestertown Romantic Hotels

The Fern Lodge
Lake view

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (46)
"We had such a great experience the first night so we moved our plans and stayed a second, next time we will definitely stay even longer."
The Fern Lodge
Sleepy Hollow, Pool/AC/Fireplace,Cabin Steps to Loon Lake
Property grounds

Sleepy Hollow, Pool/AC/Fireplace,Cabin Steps to Loon Lake

9.8 out of 10, Exceptional, (6)
"Our grandkids can’t stop talking about our stay in the Sleepy Hollow cabin. They loved the pool and Loon lake. The evenings around the fire pit were great! A special thanks to Wendy for her hospitality and to Anthony for bringing the marshmallows!"
The price is SAR 1,313
SAR 1,665 total
includes taxes & fees
6 Jul - 7 Jul
Sleepy Hollow, Pool/AC/Fireplace,Cabin Steps to Loon Lake
Trout House Village Resort
Luxury Cabin, 1 Bedroom, Lake View | Living area | 42-inch Smart TV with digital channels, DVD player, streaming services

Trout House Village Resort

3.0 star property
10.0 out of 10, Exceptional, (11)
"Absolutely wonderful place and super friendly staff "
The price is SAR 940
SAR 1,137 total
includes taxes & fees
5 Jul - 6 Jul
Trout House Village Resort
The Queensbury Hotel
Lobby

The Queensbury Hotel

3.0 star property
9.2 out of 10, Wonderful, (1260)
"Beautiful hotel!"
The Queensbury Hotel
The Villas on Lake George
Superior House, 6 Bedrooms, Lake View | Terrace/patio

The Villas on Lake George

2.5 star property
7.6 out of 10, Good, (81)
"Great place for family get away . Beautiful location lake front beach and the pool. Our tradition every year to visit Lake George "
The price is SAR 6,188
SAR 6,869 total
includes taxes & fees
26 Jul - 27 Jul
The Villas on Lake George
Waterfront paradise, hot tub. Saratoga/Lake George. Super clean & sanitized.
Outdoor dining

Waterfront paradise, hot tub. Saratoga/Lake George. Super clean & sanitized.

10.0 out of 10, Exceptional, (24)
"Our stay was perfect. David was an excellent host making me feel welcome and taken care of. "
Waterfront paradise, hot tub. Saratoga/Lake George. Super clean & sanitized.
Warm Secluded Adirondack Chalet with Game Room and Bar/Lounge
Property grounds

Warm Secluded Adirondack Chalet with Game Room and Bar/Lounge

9.8 out of 10, Exceptional, (44)
"Great stay, close to Lake George down town. "
The price is SAR 1,594
SAR 2,444 total
includes taxes & fees
18 Jul - 19 Jul
Warm Secluded Adirondack Chalet with Game Room and Bar/Lounge
Sweet New Cabin With Amazing Views Of The Hudson River
Interior

Sweet New Cabin With Amazing Views Of The Hudson River

9.8 out of 10, Exceptional, (37)
"Perfect place to stay whilst skiing at Gore!"
Sweet New Cabin With Amazing Views Of The Hudson River
Handcrafted mountain cabin with gorgeous views
Miscellaneous

Handcrafted mountain cabin with gorgeous views

9.8 out of 10, Exceptional, (43)
"We really like it there and have come to think of it as or ADK home"
The price is SAR 656
SAR 953 total
includes taxes & fees
6 Jul - 7 Jul
Handcrafted mountain cabin with gorgeous views
Camp Lillian Gorgeous New Cabin with Mountain Views
Outdoor dining

Camp Lillian Gorgeous New Cabin with Mountain Views

9.8 out of 10, Exceptional, (67)
"Beautiful little cabin! Rustic, quaint, and comfortable. Would definitely stay again!"
The price is SAR 638
SAR 928 total
includes taxes & fees
6 Jul - 7 Jul
Camp Lillian Gorgeous New Cabin with Mountain Views
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

Searching for romantic hotels in Chestertown?
If you and your partner need a romantic escape, we've got just the thing. Our guests also enjoy Chestertown for its lakeside setting. You might consider checking out some of the nearby sights and attractions such as Friends Lake, Loon Lake, or Hudson River. If you're interested in staying near a certain attraction, you can sort by neighborhood or distance to top sights, so you'll be able to see everything on your list.
How many romantic hotels are there in Chestertown?
Expedia has 12 romantic Chestertown hotels for you both to enjoy.
When is the best time of year for a romantic getaway to Chestertown?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Chestertown: The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chestertown are January, March, November, and December, with each month seeing an average of 13 inches of snowfall.
What is there to do in Chestertown?
There's nothing better than experiencing a new destination with your sweetheart, so consider checking out all that Chestertown has to offer. Couples looking to get out in nature will enjoy Chestertown for its lakeside setting. If you want to spend a day exploring, you might consider a stop at Friends Lake, Loon Lake, or Hudson River.
What's the best way to get to Chestertown and around town during my romantic getaway?
These transportation options in Chestertown might help your romantic getaway go off without a hitch: Make your way to Chestertown with a flight to Glens Falls, NY (GFL-Floyd Bennett Memorial), which is the closest major airport located 23.6 mi (38 km) from the city center. If you'd like to explore around the area, you may want a rental car for your journey.