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Top Chestertown hotels deals

Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

2 out of 5
5537 State Route 8 Chestertown NY
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This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a picnic area, and express check-in are also on offer.
Pet friendly
Parking included
Friends Lake Inn

Friends Lake Inn

4 out of 5
963 Friends Lake Rd Chestertown NY
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A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, and a lobby fireplace are also on offer.
Parking included
Free WiFi
The Fern Lodge

The Fern Lodge

3.5 out of 5
46 Fiddlehead Bay Rd. Chestertown NY
$509 nightly
The price is $566 total per night
$566 total
Dec 21 - Dec 22
Total with taxes and fees
This bed & breakfast's 8 hot tubs and gym are among the featured amenities. Enjoy the sauna and free perks like local cuisine breakfast and free self parking. A bar/lounge, a coffee shop, and a terrace are also provided.
Hot Tub
Breakfast included
Six Flags Great Escape Lodge & Indoor Waterpark

Six Flags Great Escape Lodge & Indoor Waterpark

3.5 out of 5
89 Six Flags Dr Queensbury NY
$169 nightly
The price is $188 total per night
$188 total
Dec 18 - Dec 19
Total with taxes and fees
Free water park access, 3 restaurants, and a lazy river are all featured at this resort. Bring the family and enjoy the children's club, waterslide, and arcade/game room. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.
Parking included
Free WiFi
The Queensbury Hotel

The Queensbury Hotel

3 out of 5
88 Ridge St Glens Falls NY
Free Cancellation
Reserve now, pay when you stay
$104 nightly
The price is $115 total per night
$115 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This Victorian hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and airport shuttle. Relax with a drink at one of the 2 bars/lounges and enjoy perks like free self parking.
Pool
Hot Tub
The Georgian Lakeside Resort

The Georgian Lakeside Resort

2.5 out of 5
384 Canada Street Lake George NY
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A private beach and a gym are featured at this hotel. Enjoy a day at the beach kayaking, or relax with sun loungers. Enjoy a meal from the restaurant and perks like free self parking and free WiFi.
On private beach
Pool
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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.

Popular places to visit

Friends Lake

Commune with nature and explore the great outdoors at Friends Lake during your travels in Chestertown. While you're in the area, stroll along the lakeside.

Friends Lake

Loon Lake

Commune with nature and explore the great outdoors at Loon Lake during your travels in Chestertown. While you're in the area, stroll along the lakeside.

Loon Lake

Loon Lake Beach

If a restful vacation is part of your travel plans, Loon Lake Beach might be the perfect place to seek out during your trip to Chestertown. While you're in the area, stroll along the lakeside.

Loon Lake Beach

Frequently asked questions

How much are vacation packages to Chestertown?
Vacation packages, which include flights and hotels in Chestertown, start from as little as . Make your travel dreams a reality and lock in your trip with Travelocity today.
How long should my Chestertown vacation be?
Generally, 2 nights is what most travelers book for their Chestertown trip. That's a rough guide, but there's so much more to explore if you give yourself a little longer.
Where can I get the best vacation package deals for Chestertown?
For an affordable Chestertown package deal, nothing compares to Travelocity. Take your pick of 400 airlines and 1,000,000 worldwide properties to create the ultimate escape — it couldn't be easier than that.
Why should I book my Chestertown vacation bundle via Travelocity?
With superb service, 24/7 support and some of the most perfect escapes money can buy, you'll never roam alone. And if you happen to find a lower price, we'll match it. That's our Price Match Guarantee.
Will I save money on my Chestertown car rental if I combine it with my hotel or flight?
Bundling your hotel, car and flight into a Chestertown vacation package is a surefire way to land the best deal. Plus, having your own wheels gives you absolute freedom to get to all those big sights you're hoping to check out. Situated 70 mi from Chestertown, The Egg is one attraction that should be on your must-do list. Fill up the tank and make a day trip of it.
Which airport is best for Chestertown?
One of the handiest options is Adirondack Regional Airport (SLK), roughly 55 mi north of the hustle and bustle of downtown Chestertown. Another great choice is Rutland Southern Vermont Regional Airport (RUT), 45 mi away from central Chestertown).
What is there to do in Chestertown?
There's a certain kind of magic as you stroll the streets of Chestertown. Loon Lake Beach and Friends Lake are just a couple of famous attractions that make this city such a sought-after destination, so add them to your to-do list.
Where should I stay when visiting Chestertown?
Many visitors choose to stay at the The Fern Lodge. It's an excellent base for your Chestertown getaway.

Photos of local treasures

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Photo by Julie Miller
Photo by Julie Miller