A waterfront town with a pier, dock, and several buildings.

Romantic Hotels & Resorts in Chestertown from NZ$313

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Check availability on Chestertown Romantic Hotels

Tonight
29 Sept - 30 Sept
Tomorrow
30 Sept - 1 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Chestertown romantic hotels

A cozy room with a bed, a sofa, and a balcony with chairs.
A building with a warning sign for falling snow and ice, surrounded by greenery and ferns.
A room with a wooden headboard, two beds with beige bedding, a window with a curtain, and a wall-mounted sign.
A wooden cabin with a green roof, a wooden door, and a window with shutters.

1. ADK Rustic Private Chalet Viewing Two Ponds / Forest 5.3 miles To Gore Mountain

ADK Rustic Private Chalet Viewing Two Ponds / Forest 5.3 miles To Gore Mountain
North Creek
United States
Michael G.
NZ$433
includes taxes & fees
5 Oct - 6 Oct
ADK Rustic Private Chalet Viewing Two Ponds / Forest 5.3 miles To Gore Mountain
A river with large rocks in the foreground and a forested hillside in the background.
A compact kitchen with a sink, a coffee maker, a toaster, and a small refrigerator.
A glamping site named Glamp Richard, featuring a tent with two red Adirondack chairs and a wooden deck.
A wooden room with two large circular windows, a blue floor, and a wooden bench.

2. GLAMP RICHARD ON ADIRONDACK FLOWER FARM

GLAMP RICHARD ON ADIRONDACK FLOWER FARM
North River
United States
Timothy
NZ$313
includes taxes & fees
30 Sept - 1 Oct
GLAMP RICHARD ON ADIRONDACK FLOWER FARM
A wooden room with two large circular windows, a blue floor, and a wooden bench.
A cabin surrounded by dense forest, with a clear view of the surrounding trees and a dirt path leading to the entrance.
A cozy cabin interior with a wooden interior, a kitchenette, a dining area, and a living room with a sofa and a coffee table.
A cozy cabin interior with a wooden bench by a large window, shelves with various items, and a fireplace.

3. Sweet New Cabin With Amazing Views Of The Hudson River

Sweet New Cabin With Amazing Views Of The Hudson River
North River
United States
Dave C.
NZ$484
includes taxes & fees
8 Oct - 9 Oct
Sweet New Cabin With Amazing Views Of The Hudson River
A wooden room with two large circular windows, a blue floor, and a wooden bench.
Two rustic wooden cabins surrounded by a lush forest with a variety of wildflowers.
A cozy, well-lit tent with a kitchen area featuring a sink, stove, and dining table.
An aerial view of a rural property with multiple buildings, including a bathhouse, a lodge, and a pizza hut.

4. GLAMP BERNICE ON BEAUTIFUL ADIRONDACK HOBBY FARM

GLAMP BERNICE ON BEAUTIFUL ADIRONDACK HOBBY FARM
North River
United States
Gretta G.
NZ$313
includes taxes & fees
30 Sept - 1 Oct
GLAMP BERNICE ON BEAUTIFUL ADIRONDACK HOBBY FARM
Two wooden Adirondack chairs facing a lake with a forested hillside in the background.
A room with a large black bathtub, wooden shelves with towels, a wooden bench, and a sign indicating the bathtub is for use.
A wooden room with two large circular windows, a blue floor, and a wooden bench.
A cozy room with a bed, a desk, and a window.

5. ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT

ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT
North River
United States
Amanda B.
NZ$476
includes taxes & fees
30 Sept - 1 Oct
ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT
A rustic outdoor dining area with a wooden table and benches, surrounded by greenery and a small building with large windows.
A room with a large circular black container, wooden walls, a window with blinds, a shelf with dishes, and a blue floor.
A group of people around a pizza oven with a pizza on a tray.
A cozy cabin-style room with a bed, wooden furniture, a kitchenette, and large windows.

6. Camp Lillian Gorgeous New Cabin with Mountain Views

Camp Lillian Gorgeous New Cabin with Mountain Views
North River
United States
Ken B.
NZ$447
includes taxes & fees
5 Oct - 6 Oct
Camp Lillian Gorgeous New Cabin with Mountain Views
A wooden room with two large circular windows, a blue floor, and a wooden bench.
A cozy room with a red door, a sofa with floral upholstery, a small table, and a bench.
Three Adirondack chairs facing a forest with autumn foliage and mountains in the background.
A rural farm with a small wooden house and a fenced vegetable garden.

7. Beautiful cottage on scenic Adirondack hobby farm

Beautiful cottage on scenic Adirondack hobby farm
North River
United States
Lynn V.
NZ$421
includes taxes & fees
30 Sept - 1 Oct
Beautiful cottage on scenic Adirondack hobby farm
A red building with a 'Bossie' sign, a wooden bench outside, and a view of a forested hillside.
A small cabin with a red door and green roof, labeled "BOSSIE," situated in a forested area.
A stone fireplace with a pizza being served.
A room with a large circular water feature in the center, wooden shelves with folded towels, a kettle, and a trash bin.

8. Handcrafted mountain cabin with gorgeous views

Handcrafted mountain cabin with gorgeous views
North River
United States
Anna
NZ$454
includes taxes & fees
1 Oct - 2 Oct
Handcrafted mountain cabin with gorgeous views
A wooden room with two large circular windows, a blue floor, and a wooden bench.
A tented accommodation with two beds, a small table with a lamp, and a view through a door to the outside.
Two rustic wooden cabins surrounded by a lush forest with a variety of wildflowers.
A campsite with tents and a fire.

9. GLAMP SUZANNE: CANVAS CABIN ON PRETTY ADIRONDACK FARM OFFERS PRIVACY AND VIEWS

GLAMP SUZANNE: CANVAS CABIN ON PRETTY ADIRONDACK FARM OFFERS PRIVACY AND VIEWS
North River
United States
Ari
NZ$313
includes taxes & fees
30 Sept - 1 Oct
GLAMP SUZANNE: CANVAS CABIN ON PRETTY ADIRONDACK FARM OFFERS PRIVACY AND VIEWS
A wooden room with two large circular windows, a blue floor, and a wooden bench.
A campfire with a tent in the background.
A room with a large circular black container, wooden walls, a window with blinds, a shelf with dishes, and a blue floor.
A rustic cabin with a green roof, surrounded by a snowy landscape and dense forest.

10. 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
United States
Marcia M.
NZ$466
includes taxes & fees
1 Oct - 2 Oct
RESTORED HISTORIC ADIRONDACK BIRD CAMP NEAR GORE MT WITH LOVELY MOUNTAIN VIEWS
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Top Chestertown Hotel Reviews

Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites

8/10 Good
"The hotel is very well located, and the price-to-value ratio is excellent. The room was clean and comfortable, and the front desk staff was very friendly and helpful. The only minor inconvenience was the parking. The parking area was quite full, so we had to park in a spot that was a little far from our room. However, the parking was still within the hotel property, so it was not a major issue. Overall, we had a very pleasant stay and would definitely consider staying here again."
Maria 1-night trip
Posted less than an hour ago
Adirondack Retreat Inn & Suites
Baymont by Wyndham Queensbury / Lake George

Baymont by Wyndham Queensbury / Lake George

10/10 Excellent
"It was clean and the bed was very comfy"
Carmen 2-night trip
Posted 1 day ago
Baymont by Wyndham Queensbury / Lake George

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 Loon Lake. 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 Loon Lake.
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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