Deals on vacations and trips to Chestertown

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Top Chestertown hotels deals

Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

2 out of 5
5537 State Route 8 Chestertown NY
$175 nightly
The price is $194 total per night
$194 total
Sep 9 - Sep 10
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a picnic area, and express check-out are also on offer.
Pet friendly
Parking included
Great Escape Lodge & Indoor Waterpark

Great Escape Lodge & Indoor Waterpark

3.5 out of 5
89 Six Flags Dr Queensbury NY
$146 nightly
The price is $162 total per night
$162 total
Sep 27 - Sep 28
Total with taxes and fees
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
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
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $103 total per night
$103 total
Sep 13 - Sep 14
Total with taxes and fees
This hotel features an indoor pool and a gym. There's fun for all ages with a waterslide and a playground, and families will appreciate the onsite laundry facilities. Enjoy the hot tub and free perks like continental breakfast and free self parking.
Pool
Hot Tub
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
$152 nightly
The price is $169 total per night
$169 total
Oct 6 - Oct 7
Total with taxes and fees
This hotel features an outdoor pool, an indoor pool, and a restaurant. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free self parking and free WiFi.
Pool
Parking included
The Georgian Lakeside Resort

The Georgian Lakeside Resort

2.5 out of 5
384 Canada Street Lake George NY
$105 nightly
The price is $117 total per night
$117 total
Sep 13 - Sep 14
Total with taxes and fees
A private beach and a gym are featured at this hotel. Enjoy a day at the beach kayaking, or relax with sun loungers. Enjoy a meal from the restaurant and perks like free self parking and free WiFi.
On private beach
Pool
The Queensbury Hotel

The Queensbury Hotel

3 out of 5
88 Ridge St Glens Falls NY
$134 nightly
The price is $149 total per night
$149 total
Sep 13 - Sep 14
Total with taxes and fees
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
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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.

Stay near popular Chestertown attractions

Loon Lake

8.8/10 (8 reviews)
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.
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Frequently asked questions

How much are vacation packages to Chestertown?
Vacation packages, which include flights and hotels in Chestertown, start from as little as . 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

Browse Chestertown vacation photos for more inspiration

A waterfront town with a pier, dock, and several buildings.
A red bridge over a river with houses and greenery on both sides.
A snowy lodge with cabins and tall pine trees.