Deals on vacations and trips to Chestertown

Save when you book Chestertown package deals

Choose two or more items and save on your trip:

Chestertown flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Little Twister Sister by Avantstay Heated Pool + Game Lounge Near Gore

Little Twister Sister by Avantstay Heated Pool + Game Lounge Near Gore

3 out of 5
Price was $928, price is now $795 per person
$795
per person
Sep 18 - Sep 23
found 19 hours ago
Roundtrip non-stop flight included
Rochester (ROC) to Glens Falls (GFL)
This cottage features an outdoor pool and a sauna. Guests will appreciate free perks like free self parking and WiFi in public areas. Barbecue grills are provided for your convenience.
Twin Fawns by Avantstay Ski Retreat + Deck Indoor Heated Pool + Rec Center Access Trails & Slopes

Twin Fawns by Avantstay Ski Retreat + Deck Indoor Heated Pool + Rec Center Access Trails & Slopes

3 out of 5
Price was $1,044, price is now $894 per person
$894
per person
Sep 18 - Sep 23
found 19 hours ago
Roundtrip non-stop flight included
Rochester (ROC) to Glens Falls (GFL)
This cottage features an outdoor pool and a sauna. Guests will appreciate free perks like free self parking and WiFi in public areas. Barbecue grills are provided for your convenience.
Echo by Avantstay Sauna + Indoor Pool + Fireplace Near Gore Mountain

Echo by Avantstay Sauna + Indoor Pool + Fireplace Near Gore Mountain

3 out of 5
Price was $985, price is now $845 per person
$845
per person
Sep 18 - Sep 23
found 19 hours ago
Roundtrip non-stop flight included
Rochester (ROC) to Glens Falls (GFL)
This cottage features an outdoor pool and a sauna. Guests will appreciate free perks like free self parking and WiFi in public areas. Barbecue grills are provided for your convenience.
Sagamore by Avantstay Heated Pool + Game Room Near Gore + Main St

Sagamore by Avantstay Heated Pool + Game Room Near Gore + Main St

3 out of 5
Price was $1,025, price is now $879 per person
$879
per person
Sep 18 - Sep 23
found 19 hours ago
Roundtrip non-stop flight included
Rochester (ROC) to Glens Falls (GFL)
This cottage features an outdoor pool and a sauna. Guests will appreciate free perks like free self parking and WiFi in public areas. Barbecue grills are provided for your convenience.
Hawkeye by Avantstay Indoor Heated Pool + Rec Lounge Near Gore + Main St

Hawkeye by Avantstay Indoor Heated Pool + Rec Lounge Near Gore + Main St

3 out of 5
Price was $959, price is now $825 per person
$825
per person
Sep 18 - Sep 23
found 19 hours ago
Roundtrip non-stop flight included
Rochester (ROC) to Glens Falls (GFL)
This cottage features an outdoor pool and a sauna. Guests will appreciate free perks like free self parking and WiFi in public areas. Barbecue grills are provided for your convenience.

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
Aug 20 - Aug 21
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.
Peaceful Lakeside Retreat with Private Beach

Peaceful Lakeside Retreat with Private Beach

Chestertown NY
Get rates
This condo includes a garden and laundry facilities.
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 7 - Sep 8
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.
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 14 - Sep 15
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
Great Escape Lodge & Indoor Waterpark

Great Escape Lodge & Indoor Waterpark

3.5 out of 5
89 Six Flags Dr Queensbury NY
$185 nightly
The price is $205 total per night
$205 total
Sep 18 - Sep 19
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
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
$149 nightly
The price is $165 total per night
$165 total
Sep 7 - Sep 8
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.
Don't see what you're looking for?
See all available properties in Chestertown
View all properties
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.
See properties

Frequently asked questions

How much are vacation packages to Chestertown?
Vacation packages, which include flights and hotels in Chestertown, start from as little as $795. 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.