Cheap Flights to Chestertown

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Chestertown Flight Information

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Chestertown
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Find The Perfect Hotel For After Your Flight

Family Friendly Hotels in Chestertown

Pine Tree Motel & Cabins
Great for families

Pine Tree Motel & Cabins

2 out of 5
5537 State Route 8, Chestertown, NY
The price is $175 per night from May 16 to May 17
$175
per night
May 16 - May 17
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 nearby. ...
9/10 Wonderful! (113 reviews)

Families like: Playground, close to beach, extra beds/cribs, games and toys

Travelers say...
"Cutest cabins, friendly owners, dog friendly ❤️ supporting small businesses definitely going back next year."

Reviewed on Oct 10, 2023

Pine Tree Motel & Cabins
Friends Lake Inn

Friends Lake Inn

4 out of 5
963 Friends Lake Rd, Chestertown, NY
The price is $176 per night from Apr 28 to Apr 29
$176
per night
Apr 28 - Apr 29
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! (77 reviews)
"The food was made to order and very good prices were fair. The cost to stay there is overpriced."

Reviewed on Feb 6, 2023

Friends Lake Inn
Lily Pad South at Loon Lake near Gore Mountain
Great for families

Lily Pad South at Loon Lake near Gore Mountain

Chestertown
Stay at this apartment in Chestertown. Enjoy WiFi, onsite parking, and a garden. Popular attractions Loon Lake and Loon Lake Beach are located nearby. Discover ...
9.6/10 Exceptional! (39 reviews)

Families like: Kitchen, close to beach, washer and dryer

Travelers say...
"What I loved most was it was like staying in your own home, quiet, clean, and private. The only drawback was no coffee in the kitchen. Otherwise absolutely give stars. I want to stay in this exact house again if welcome. They were very nice, too, and accommodating."

Reviewed on Mar 17, 2024

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Lily Pad South at Loon Lake near Gore Mountain
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The Fern Lodge
Great for families

The Fern Lodge

3.5 out of 5
46 Fiddlehead Bay Rd., Chestertown, NY
The price is $599 per night from Apr 26 to Apr 27
$599
per night
Apr 26 - Apr 27
Stay at this 3.5-star 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! (36 reviews)

Families like: Game room, skiing nearby, free breakfast for the whole family, laundry

Travelers say...
"Paradise just simply heavenly. And so well appointed. Feel so at home"

Reviewed on Oct 15, 2023

The Fern Lodge
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.

Need a Car For After Your Flight?

Economy

Chevrolet Spark or similar
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Jeep Compass
SUV Jeep Compass

Frequently asked questions

Which airlines fly to Chestertown?
Book your plane ticket with one of the 7 airlines that fly to Chestertown. Experienced travelers often prefer to fly with these carriers:

  • American Airlines
  • Delta Air Lines
  • United Airlines

What airport is best to fly into Chestertown?
Flying in and out of Chestertown is easy, as it’s serviced by just one airport. You’ll find Albany International Airport roughly 60 mi from the sights and sounds of downtown.
Where to stay in Chestertown
Start making those dreams about Chestertown come true by booking your accommodations through Travelocity. With 179 fabulous options at your fingertips, we know you’ll find the ideal place to base yourself.There’s no more suitable time to spoil yourself than when you’re taking a vacation. Lock in a room at the Friends Lake Inn and enjoy a taste of the good life during your stay. Watching your budget? Not to worry, you won’t be left out in the cold. The Pine Tree Motel & Cabins will keep you and your bank account happy.
Places to visit in Chestertown
Many tourists like visiting Friends Lake. Pack a lunch and simply relax by the water. Like some more options? If you’re ever sick of the heat, go to Loon Lake Beach, where you’ll find cool relief in the soothing water. But there’s more. Many visitors love admiring Tripp Pond. Pack a picnic and simply relax by the water.
How to get through airport security fast when traveling to Chestertown
These useful tips and pointers about airport security will save you plenty of time on your journey to Chestertown:

  • Make sure your travel ID and boarding pass are easily accessible. You’ll be required to present them straightaway.
  • You’ll need to pause the tunes for a little while. Earphones and headphones must be removed and placed in a tray for X-raying. The same applies to items such as belts and heavy jackets.
  • Digital cameras, laptops and other electronic devices must be placed in separate bins to be X-rayed.
  • When it comes to flying with liquids and gels, all passengers are allowed a quart-sized clear zip-lock bag to keep containers no bigger than 3.4 ounces (100 milliliters).
  • Undo your shoelaces as you approach the body scanner. Depending on the type of shoes you’ve got on, security may ask you to take them off.
  • Some places have stringent quarantine laws. Think about where you’re headed to and whether or not you’re permitted to fly with fruit and meats.

How to find cheap flights

What is the best day to buy a plane ticket?

Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you’re looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you’re browsing flight deals.

 

What are the cheapest days to fly?

Frequent travellers may already know this, earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.

 

How far in advance can you book a flight?

Here’s the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.

*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

Plane Tickets To Chestertown

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Chestertown. Browse through our inventory to explore a wide range of cheap flights to Chestertown to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Chestertown as you anxiously await to exit the plane and explore what Chestertown has to offer. Considering all the amazing local food and culture in Chestertown, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Chestertown to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Chestertown without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Chestertown with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Chestertown today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.