Chestertown Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence
    • payments icon
    Better together
    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Chestertown Holiday

There's plenty to like about Chestertown, from its rich history to its spectacular views and beyond. When you're ready to spend a bit of time in this fascinating city, our Chestertown holiday packages will be just the thing. You'll want to sightsee during your trip to Chestertown. Carve out some time for leading attractions such as Friends Lake, Loon Lake and Loon Lake Beach. Your dream Chestertown holiday is clicks away. Browse airfares, hotels and more on Expedia for a getaway that's tailored just for you.

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Chestertown Holiday

Chestertown Essential Information

Language
English
Currency
U.S dollars
Population
680
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Gore Mountain Ski Resort, Loon Lake Beach and Natural Stone Bridge and Caves

Our pick of the best Chestertown Hotel Deals

Six Flags Lodge & Indoor Waterpark
Six Flags Lodge & Indoor Waterpark
3.5 out of 5
89 Six Flags Dr, Queensbury, NY
The price is AU$286 per night from 24 Nov to 25 Nov
AU$286
includes taxes & fees
24 Nov - 25 Nov
7.6/10 Good! (1,009 reviews)
"Its a vary nice and family oriented place"

Reviewed on 18 Nov. 2024

Six Flags Lodge & Indoor Waterpark
The Queensbury Hotel
The Queensbury Hotel
3 out of 5
88 Ridge St, Glens Falls, NY
Fully refundableReserve now, pay when you stay
The price is AU$175 per night from 24 Nov to 25 Nov
AU$175
includes taxes & fees
24 Nov - 25 Nov
9/10 Wonderful! (1,178 reviews)
"The room was very small. It did not have a microwave or small refrigerator. We didn’t realize the pool and hot top was closed. We couldn’t find our reservation on Expedia or Hotels.com even with the reservation #."

Reviewed on 17 Nov. 2024

The Queensbury Hotel
La Quinta Inn & Suites by Wyndham Lake George
La Quinta Inn & Suites by Wyndham Lake George
2 out of 5
1533 US-9, Lake George, NY
Fully refundableReserve now, pay when you stay
The price is AU$167 per night from 3 Dec to 4 Dec
AU$167
includes taxes & fees
3 Dec - 4 Dec
8.8/10 Excellent! (1,503 reviews)
"Very nice hotel. Only issue were the tons of kids running around unattended … they were in the fitness room, dripping wet from the pool with no shoes on and no adults watching them."

Reviewed on 18 Nov. 2024

La Quinta Inn & Suites by Wyndham Lake George
See all 1,482 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Chestertown holiday package cost?
We make it simple to travel somewhere new, with Chestertown holiday packages starting from as little as . You’ll have the flexibility to combine your favourite hotels, airlines and car rental. For the ultimate escape, why not add a few experiences and tours to your travel itinerary?
How do I get a cheap travel package to Chestertown?
You’ll save loads of cash if you combine your flights, hotels and car rentals into a Chestertown travel package. Sometimes cheap packages mean fewer options. But not with Expedia. We offer over 550 partner airlines and 1 000 000 hotels worldwide, which means you’ll always have plenty of options to choose from. Like to save even more? Add some exciting activities to your package deal and unlock even more bargains! After all, travel is about more than simply getting to your destination.
Where should I stay in Chestertown?
Stay where the action is. Many people book hotels around top attractions, such as Loon Lake Beach, Friends Lake and Loon Lake.
What are the top hotels in Chestertown?
Log Haven, Pool And Ac, Cosy Adirondack Mountains Cabin Steps From Loon Lake and Deer Run, Pool, Adirondack Cabin are two of the most sought-after hotels in Chestertown. Why not check out the amenities and facilities at each and then make a decision?
How far in advance should I book my Chestertown holiday?
It depends on the airline, but you can usually browse through international airfares on Expedia up to 12 months in advance. While it’s advisable to book ahead of time, lucky travellers occasionally score a cheaper seat only weeks before departure dates.
What does an Expedia Chestertown travel package include?
With Expedia, you can choose a combination of hotels, flights and car rentals to create your ideal Chestertown travel package. Once you’ve made your booking, you can add on the fun things like sightseeing tours and activities. Don’t forget, the more you bundle, the bigger the savings!
What should I know before booking a Chestertown travel package?
Locking in all the parts of your getaway together is a smart way to save. Bundle your car rentals, flights and hotels into a tidy little package. But it’s not just hotels. Expedia has all kinds of properties, including holiday homes such as beachside villas and short-term homes. The list goes on!
Can I choose my airline with a Chestertown Expedia holiday package?
Yes — and it’s easy too. Expedia has access to more than 550 partner airlines all over the world. Our holiday packages give you the freedom to pick from available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Chestertown holiday package?
You can. We get that life happens, so we’re here to help if you have to make changes to your Chestertown holiday package. You may be able to change or cancel your itinerary for free if you’ve booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Head to our Customer Service Portal for further information. Also, check your itinerary for the finer details on change fees.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.