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How Much Does it Cost To Fly To Chestertown?

The cheapest flights to Chestertown found within the past 7 days were $102. Prices and availability subject to change. Additional terms may apply.


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!

Chestertown Flights - Frequently Asked Questions

  • Question : Which hotels are located near airports or major attractions in Chestertown?
    Answer : We've put together a list of hotels in Chestertown close to airports and popular sights to see. Check out the hotels below. All of them are within proximity to must-see attractions and major airports in and around the city of Chestertown.
    • The Fern Lodge: Situated on a lake, this bed & breakfast is 4 mi (6.4 km) from Loon Lake Beach and 8.1 mi (13 km) from Pack Demonstration Forest. Natural Stone Bridge and Caves and Hickory Ski Center are also within 16 mi (25 km). This hotel has a 3.50 star rating.
    • Pine Tree Motel & Cabins: Situated near the beach, this motel is 0.6 mi (1 km) from Loon Lake Beach and within 12 mi (20 km) of Pack Demonstration Forest and Natural Stone Bridge and Caves. Tannery Pond Community Center and North Creek Depot Museum are also within 16 mi (25 km). This hotel has a 2.00 star rating.
    • Friends Lake Inn: Offering ski-in/ski-out access, this hotel in Chestertown is in the mountains, 2.5 mi (4.1 km) from Loon Lake Beach, and close to winter activities such as snow tubing and sledding. Pack Demonstration Forest and Natural Stone Bridge and Caves are also wit This hotel has a 4.00 star rating.

Travelers ❤️ These 🏨

Estimated price for 1 night/2 adults

Friends Lake Inn
Friends Lake Inn
4.0 out of 5.0 963 Friends Lake Rd, Chestertown, NY
$199
Offering ski-in/ski-out access, this hotel in Chestertown is in the mountains, 2.5 mi (4 km) from Loon Lake Beach, and close to winter activities such as snow ...
The Fern Lodge
The Fern Lodge
3.5 out of 5.0 46 Fiddlehead Bay Rd., Chestertown, NY
$395
5.0/5 (1 reviews)

My husband and I just left The Fern Lodge a few hours ago and miss it already. It was such a welcoming and relaxing place. Sharon made us feel right at home, from the delicious breakfast to the fire and glass of wine in the evening. The pictures you see on their website are exactly what you get when ...

Reviewed on Nov 8, 2012
Situated in Chestertown, this bed & breakfast is 4 mi (6.4 km) from Loon Lake Beach and within 12 mi (20 km) of Pack Demonstration Forest and Natural Stone Bridge ...
Family Friendly Authentic Rustic LOG Condo
Family Friendly Authentic Rustic LOG Condo
Chestertown, NY
Situated in a rural location, this romantic property is 5.2 mi (8.3 km) from Pack Demonstration Forest and within 12 mi (20 km) of Loon Lake Beach and Hickory ...

* This is the largest savings for simultaneous booking of flight and hotel from July 1, 2015 to June 30, 2016, and not the discount rate or amount for your booking. Savings calculated based on the cost of a Flight + Hotel booking on Travelocity.com as compared to the aggregated price of the full published fare given by the airline and the cost of your hotel for the same travel products for the same travel dates when made separately. Savings will vary based on the origin/destination, length of trip, stay dates and selected travel supplier(s). Savings are not available on all packages. Please confirm the actual discount rate/ price on the booking page.