Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

Romantic Hotels & Resorts in Chestertown from NZ$247

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Check availability on Chestertown Romantic Hotels

Our top choices for Chestertown romantic hotels

Lake George Water Front Cabin Spectacular Views

Lake George Water Front Cabin Spectacular Views
Ticonderoga
9.6 out of 10, Exceptional, (35 reviews)
"Super pretty views and a very quiet and tranquil stay :)"
United States
Mackenzie C.
The price is NZ$1,972
includes taxes & fees
16 June - 17 June
Lake George Water Front Cabin Spectacular Views

Secluded retreat. Great for families. Walk to Trout lake. High Speed Internet.

Secluded retreat. Great for families. Walk to Trout lake. High Speed Internet.
Diamond Point
9.8 out of 10, Exceptional, (59 reviews)
"We enjoyed our trip and the house was very comfortable and clean and well updated."
United States
Nuala D.
The price is NZ$1,575
includes taxes & fees
11 June - 12 June
Secluded retreat. Great for families. Walk to Trout lake. High Speed Internet.

ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT

ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT
North River
10.0 out of 10, Exceptional, (99 reviews)
"This cabin was so cute and comfortable! It had everything we needed plus a view! Can’t wait to stay again "
United States
Amanda B.
The price is NZ$409
includes taxes & fees
12 June - 13 June
ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT

GLAMP RICHARD ON ADIRONDACK FLOWER FARM

GLAMP RICHARD ON ADIRONDACK FLOWER FARM
North River
9.4 out of 10, Exceptional, (21 reviews)
"Peaceful weekend with family. "
United States
Timothy
The price is NZ$247
includes taxes & fees
11 June - 12 June
GLAMP RICHARD ON ADIRONDACK FLOWER FARM

GLAMP BERNICE ON BEAUTIFUL ADIRONDACK HOBBY FARM

GLAMP BERNICE ON BEAUTIFUL ADIRONDACK HOBBY FARM
North River
9.8 out of 10, Exceptional, (41 reviews)
"We had such a wonderful time! The location is so peaceful and scenic and the drive to 13th lake for swimming was just a few minutes. Absolutely hope to stay again!"
United States
Gretta G.
The price is NZ$315
includes taxes & fees
11 June - 12 June
GLAMP BERNICE ON BEAUTIFUL ADIRONDACK HOBBY FARM

Camp Lillian Gorgeous New Cabin with Mountain Views

Camp Lillian Gorgeous New Cabin with Mountain Views
North River
9.8 out of 10, Exceptional, (81 reviews)
"Beautiful place and the cabin was perfect for local skiing and hiking."
United States
Ken B.
The price is NZ$409
includes taxes & fees
11 June - 12 June
Camp Lillian Gorgeous New Cabin with Mountain Views

Beautiful cottage on scenic Adirondack hobby farm

Beautiful cottage on scenic Adirondack hobby farm
North River
9.6 out of 10, Exceptional, (67 reviews)
"Cozy cabin, attentive host, wonderful amenities "
United States
Margaret P.
The price is NZ$376
includes taxes & fees
11 June - 12 June
Beautiful cottage on scenic Adirondack hobby farm

Handcrafted mountain cabin with gorgeous views

Handcrafted mountain cabin with gorgeous views
North River
10.0 out of 10, Exceptional, (51 reviews)
"Wonderful cabin, very peaceful. "
United States
Anna
The price is NZ$420
includes taxes & fees
11 June - 12 June
Handcrafted mountain cabin with gorgeous views

Sweet New Cabin With Amazing Views Of The Hudson River

Sweet New Cabin With Amazing Views Of The Hudson River
North River
9.8 out of 10, Exceptional, (47 reviews)
"Fab cabin and loved the Japanese hot tub. Close to restaurants short drive and also close to gore mountain. We loved our stay!! "
United States
Ashling
The price is NZ$474
includes taxes & fees
14 June - 15 June
Sweet New Cabin With Amazing Views Of The Hudson River

RESTORED HISTORIC ADIRONDACK BIRD CAMP NEAR GORE MT WITH LOVELY MOUNTAIN VIEWS

RESTORED HISTORIC ADIRONDACK BIRD CAMP NEAR GORE MT WITH LOVELY MOUNTAIN VIEWS
North River
9.2 out of 10, Wonderful, (67 reviews)
"Had a great stay. Camp had rustic feel and was off the beaten path. Would stay again."
United States
Marcia M.
The price is NZ$451
includes taxes & fees
11 June - 12 June
RESTORED HISTORIC ADIRONDACK BIRD CAMP NEAR GORE MT WITH LOVELY 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.

Top Chestertown Hotel Reviews

Frequently asked questions

Searching for romantic hotels in Chestertown?
If you and your partner need a romantic escape, we'd like to help you plan for it. Our guests also enjoy Chestertown for its lakeside setting. You might consider checking out some of the nearby sights and attractions such as Loon Lake Beach, Friends Lake or Hudson River. If you're interested in staying close to a certain attraction, you can sort properties by neighbourhood or distance to top sights, so you and your partner will get to see everything on your list.
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, take a look at these details about year-round temperatures in Chestertown: The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chestertown are January, March, November and December, with each month seeing an average of 33 cm of snowfall.
What is there to do in Chestertown?
There's nothing better than seeing 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 stopping at Loon Lake Beach, Friends 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 trip 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 centre. If you'd like to explore around the area, consider renting a car to explore more sights.

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