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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! (133 reviews)
"Off the beaten path. Definitely not top notch but acceptable for a camping type atmosphere."

Reviewed on Aug 1, 2025

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Pine Tree Motel & Cabins
Friends Lake Inn

Friends Lake Inn

4 out of 5
963 Friends Lake Rd, Chestertown, NY
Stay at this 4-star hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Friends Lake and Loon Lake Beach are located ...
8.8/10 Excellent! (91 reviews)
"We visited the Inn hotel to celebrate my husband’s birthday and take a much-needed break from my role as a caregiver for my mother. The weekend turned out to be exactly what we needed—it gave us the chance to unplug, recharge, and truly rest. The staff were friendly, accommodating, and just lovely ..."

Reviewed on Jun 23, 2025

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Friends Lake Inn
The Queensbury Hotel

The Queensbury Hotel

3 out of 5
88 Ridge St, Glens Falls, NY
Stay at this 3-star business-friendly hotel in Glens Falls. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the bar in ...
9.2/10 Wonderful! (1,299 reviews)
"Didn't like small bathroom"

Reviewed on Aug 2, 2025

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The Queensbury Hotel
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
Stay at this 3.5-star family-friendly resort in Queensbury. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the breakfast and the helpful ...
7.6/10 Good! (1,200 reviews)
"Great for families featuring plenty of activities including water park and arcade. We liked the room layout of two queens and a sofa bed, it was also very spacious. Parking was easy. It was nice that we could use the water park the day of check-in and the day of check out. Concessions in the water ..."

Reviewed on Aug 2, 2025

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Six Flags Great Escape Lodge & Indoor Waterpark
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! (878 reviews)
"The room was very standard. Nothing to speak off other than that you should have a safe in every room. That was very lacking. There was a lot of space in the room that wasnt used. Lighting in the room was not good. The curtain seperators should go from either end, so no one can stare in the middle. ..."

Reviewed on Aug 2, 2025

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The Georgian Lakeside Resort
Lakefront Terrace Resort

Lakefront Terrace Resort

3 out of 5
2998 Lake Shore Dr, Lake George, NY
Stay at this 3-star beach hotel in Lake George. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in ...
8/10 Very Good! (926 reviews)
"We loved the location. Not far from the village, the beach was right outside our door. Lounch chairs and umbrellas were there.They provided picnic tables complete with umbrellas and grills outside our rooms. Lawn games and a play area for children. They truelly maintained the property and beach area ..."

Reviewed on Aug 1, 2025

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Lakefront Terrace Resort
La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George

3 out of 5
1533 US-9, Lake George, NY
Stay at this 3-star family-friendly hotel in Lake George. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
8.8/10 Excellent! (1,723 reviews)
"We were there for a memorial service so we did not get a chance to really enjoy the amenities. The pool looked fantastic and the breakfast was very good. A lot of choices. The bed was very comfortable and I loved the bathroom mirror. It was lit by touch - very cool. The staff was very friendly and ..."

Reviewed on Aug 2, 2025

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La Quinta Inn & Suites by Wyndham Lake George
Best Western of Lake George

Best Western of Lake George

2.5 out of 5
2452 State Route 9N, Lake George, NY
Book a stay at this business-friendly hotel in Lake George. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.8/10 Good! (1,002 reviews)
"I liked the breakfast and pools. I didn't like the bathroom: the sink was low drain and the shower had mold stains. Also, we were in 3 people and there was only 2 sets of towels. I asked one more, I have to wait more than one hour to receive the towel. The same happened to the microwave I ..."

Reviewed on Jul 27, 2025

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Best Western of Lake George
See all 1,542 properties in Chestertown
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.