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Chestertown

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Cheap Flights to Chestertown

Fall in love at first flight with your vacation to Chestertown by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Chestertown on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Chestertown, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Chestertown

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chestertown with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the GFL airport.

What is the cheapest month to fly to Chestertown?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Chestertown are in , but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chestertown?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find  to choose from for your flight to Chestertown.

What airport is best to fly into Chestertown?

When you’re planning your trip to Chestertown, convenience is the name of the game. Luckily, Chestertown Floyd Bennett Memorial Airport is nearby so you can deplane and get going on checking off everything on your Chestertown must-do list.

How much are flights to Chestertown?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chestertown on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as , you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Chestertown?

The trick to saving a stack of cash on your flight to Chestertown? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as  right now, why wait?

Chestertown Flight Information
Destination airport
Chestertown
Destination airport IATA code
GFL

Last Minute Hotel Deals in Chestertown

Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

2 out of 5
5537 State Route 8 Chestertown NY
Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Loon Lake Beach and Loon Lake are located ...
9.2/10 Wonderful! (146 reviews)
We attended the Warrensburg Largest Garage Sale Weekend. The Motel is only 20 minutes away from the event. Located near Chestertown so you can go out to eat or grab groceries at the local Grocery Store. Motel is Dog Friendly and we did not have any issues with the Wi-Fi.

Reviewed on Oct 5, 2025

Pine Tree Motel & Cabins
Friends Lake Inn

Friends Lake Inn

4 out of 5
963 Friends Lake Rd Chestertown NY
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Friends Lake and Loon Lake Beach are located ...
8.6/10 Excellent! (102 reviews)
Staff was great. The inn is unique. Perfect!

Reviewed on Sep 7, 2025

Friends Lake Inn
The Fern Lodge

The Fern Lodge

3.5 out of 5
46 Fiddlehead Bay Rd. Chestertown NY
Book a stay at this beach B&B in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Friends Lake and Loon Lake Beach are located ...
9.8/10 Exceptional! (45 reviews)
Absolutely beautiful

Reviewed on Oct 22, 2025

The Fern Lodge
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
Book a stay at this family-friendly resort in Queensbury. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the breakfast and the helpful staff ...
7.8/10 Good! (1,392 reviews)
Todo muy bien lo único que no me gusto es que las camareras no vienen ni a preguntar si necesitan algo. Gracias a Dios la pase bien en familia

Reviewed on Dec 2, 2025

Six Flags Great Escape Lodge & Indoor Waterpark
The Queensbury Hotel

The Queensbury Hotel

3 out of 5
88 Ridge St Glens Falls NY
Book a stay at this business-friendly hotel in Glens Falls. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful ...
9.2/10 Wonderful! (1,452 reviews)
The room and bathroom were clean. The staff was very friendly and professional. The lobby was gorgeously decorated for the holidays and I loved the trio playing. So fun!

Reviewed on Dec 2, 2025

The Queensbury Hotel
Holiday Inn Resort Lake George - Adirondack Area by IHG

Holiday Inn Resort Lake George - Adirondack Area by IHG

3 out of 5
2223 Canada St Lake George NY
Book a stay at this family-friendly hotel in Lake George. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...
9.2/10 Wonderful! (1,000 reviews)
Everyone was so nice and welcoming Room is clean Convenient location Restaurant food was delicious

Reviewed on Nov 21, 2025

Holiday Inn Resort Lake George - Adirondack Area by IHG
The Georgian Lakeside Resort

The Georgian Lakeside Resort

2.5 out of 5
384 Canada Street Lake George NY
Book a stay at this beach hotel in Lake George. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the restaurant in our reviews. ...
8.6/10 Excellent! (1,000 reviews)
The room was spotless, bed & pillows were comfortable. We arrived at night and were surprised at that great view in the morning! My teenagers appreciated the list of channels and the good wi-fi connection. We all recommend ++

Reviewed on Nov 3, 2025

The Georgian Lakeside Resort
Courtyard by Marriott Lake George

Courtyard by Marriott Lake George

3 out of 5
365 Canada Street Lake George NY
Book a stay at this business-friendly hotel in Lake George. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the bar and the helpful ...
9/10 Wonderful! (1,000 reviews)
Overall it is so clean, great service, close to the village. We love it here!

Reviewed on Dec 1, 2025

Courtyard by Marriott Lake George
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.