Deals on vacations and trips to Chestertown

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Chestertown flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Queensbury/Lake George

Days Inn by Wyndham Queensbury/Lake George

2 out of 5
per person
Jul 11 - Jul 13
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Glens Falls (GFL)
A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A business center, a garden, and a grocery/convenience store are also on offer.
The Queensbury Hotel

The Queensbury Hotel

3 out of 5
per person
Jul 17 - Jul 20
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Glens Falls (GFL)
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.
The Alpine Lodge

The Alpine Lodge

3 out of 5
per person
Jul 11 - Jul 13
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Glens Falls (GFL)
This lodge doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a picnic area, and express check-in are also on offer.
Llama House ADK

Llama House ADK

2.5 out of 5
per person
Jul 11 - Jul 13
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Glens Falls (GFL)
This lodge doesn't skimp on freebies - guests receive free WiFi and free self parking. A lobby fireplace, a communal living room, and a library are also on offer.
Holiday Inn Express Queensbury - Lake George Area by IHG

Holiday Inn Express Queensbury - Lake George Area by IHG

2.5 out of 5
per person
Aug 13 - Aug 16
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Glens Falls (GFL)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

Top Chestertown hotels deals

Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

2 out of 5
5537 State Route 8, Chestertown, NY
Get rates
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
The Queensbury Hotel

The Queensbury Hotel

3 out of 5
88 Ridge St, Glens Falls, NY
Free Cancellation
Reserve now, pay when you stay
Get rates
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
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
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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
Waterfront Home on Lake George w/ Boat Dock!

Waterfront Home on Lake George w/ Boat Dock!

3 out of 5
Get rates
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.
Kitchen
Parking included
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!

HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!

3 out of 5
19 Skyline Drive, PO Box 269, Bolton Landing, NY
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This castle doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace is also provided.
Parking included
Free WiFi
Walk to Million Dollar Beach from this awesome Cottage!

Walk to Million Dollar Beach from this awesome Cottage!

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This cottage features a water park, a garden, and laundry facilities. Barbecue grills are provided for your convenience.
Kitchen
Washer
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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

5/5(3 reviews)

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 $453. 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