Chestertown Vacations

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    Save up to SARĀ 5,400 when you book a flight and hotel together*

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Find the Best Chestertown Vacation Packages

Chestertown Hotel Deals

Peaceful Lakeside Retreat with Private Beach

Peaceful Lakeside Retreat with Private Beach

Chestertown NY
9.4/10 Exceptional! (24 reviews)
"The condo / townhouse was very clean and updated. The host, Jessica was also very helpful and responsive. Overall a great stay!"

Reviewed on 10 July 2026

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Peaceful Lakeside Retreat with Private Beach
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
Fully refundableReserve now, pay when you stay
The price is SARĀ 504 per night from Jul 19 to Jul 20
SARĀ 504
SARĀ 559 total
19 Jul - 20 Jul
includes taxes & fees
8.8/10 Excellent! (1,646 reviews)
"UNSANITARY!! Horrible!! Blood and urine stains on beds!! Firstly, Iā€™ll start by mentioning that this was our second time coming here but never again!! Last year it was fine, cleaner and better management! Did they change owners?!! My family of 4 with two young kids had to leave at 10 pm after arriving ..."

Reviewed on 17 July 2026

La Quinta Inn & Suites by Wyndham Lake George
Six Flags Great Escape Lodge & Indoor Waterpark

Six Flags Great Escape Lodge & Indoor Waterpark

3.5 out of 5
89 Six Flags Dr Queensbury NY
The price is SARĀ 770 per night from Aug 12 to Aug 13
SARĀ 770
SARĀ 855 total
12 Aug - 13 Aug
includes taxes & fees
Six Flags Great Escape Lodge & Indoor Waterpark
See all 1,662 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.

Stay near popular Chestertown attractions

Loon Lake

8.8/10 (8 reviews)
Loon Lake's crystal-clear waters provide a peaceful Adirondack Mountain retreat for outdoor enthusiasts. Rent a kayak to glide across the serene surface or cast a line for native fish from the sandy public beach.
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Frequently asked questions

How much does a Chestertown vacation package cost?
You'll find cheap prices on Expedia for your Chestertown break. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Chestertown costs.
What are the cheapest months to go to Chestertown?
The off-season is the best time to travel to Chestertown if you're trying to save. Another tip for getting cheap Chestertown vacation packages? Try to avoid public holidays and any major festivals or events.
How to find the best Chestertown package deals?
Finding a cheap Chestertown package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget range, add some filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most affordable Chestertown package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Chestertown vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and hotels separately. Better still, you can customize your Chestertown trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Chestertown?
If you're considering a spontaneous Chestertown vacation, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Chestertown?

  1. Choose when to go: Check your diary and get your bags packed. Your favorite season and the activities on offer will also help you decide when to visit Chestertown.
  2. Budget wisely: In addition to the price of your hotel, you should factor in other expenses too. These include transportation, food and flights. Also, put aside some extra funds for unexpected costs that could arise during your trip to Chestertown.
  3. Work out your trip length: Think about how much time you'd like to spend discovering Chestertown. Plan your itinerary so you can get to all the attractions and activities you're interested in without rushing.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Chestertown vacation package that brings all your bookings together.