Chestertown Vacation Packages

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Your Chestertown Vacation

There's plenty to like about Chestertown, from its rich history to its spectacular views. When you're ready to spend a bit of time in this interesting city, our Chestertown vacation packages will be ideal for you. Friends Lake, Loon Lake and Loon Lake Beach are just a few of the sights you'll want to see during your trip to Chestertown. Don't put off your visit to this destination any longer. Your dream Chestertown vacation is only a few clicks away with Expedia.

Top Chestertown Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Queensbury Hotel

The Queensbury Hotel

3 out of 5
Price was CA $1,425, price is now CA $1,345 per person
CA $1,345
per person
Sep 13 - Sep 18
found 9 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Glens Falls (GFL)
9.4/10 Exceptional! (1,608 reviews)
ALL of the staff were incredibly professional and friendly. Special thanks to Kendra, of the housekeeping staff.

Reviewed on Jul 6, 2026

Chestertown Beach Vacation

Escape the stresses of daily life and let your body, mind and soul completely relax during your Chestertown vacation. Few things are more invigorating than the cool sea breeze and the soothing sound of waves lapping at the shore. Organize your trip to Chestertown the quick and easy way by locking in one of our Chestertown vacation deals. Many visitors opt to base themselves near Loon Lake Beach, a must-see only 3 kilometres from the downtown area.

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Chestertown Hotel Deals

Peaceful Lakeside Retreat with Private Beach

Peaceful Lakeside Retreat with Private Beach

Chestertown NY
Get rates
Peaceful Lakeside Retreat with Private Beach
The Queensbury Hotel

The Queensbury Hotel

3 out of 5
88 Ridge St Glens Falls NY
The price is CA $190 per night from Jul 12 to Jul 13
CA $190
CA $211 total
Jul 12 - Jul 13
includes taxes & fees
9.4/10 Exceptional! (1,622 reviews)
"ALL of the staff were incredibly professional and friendly. Special thanks to Kendra, of the housekeeping staff."

Reviewed on Jul 6, 2026

The Queensbury Hotel
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
The price is CA $228 per night from Jul 12 to Jul 13
CA $228
CA $253 total
Jul 12 - Jul 13
includes taxes & fees
8.8/10 Excellent! (1,666 reviews)
"everything great, breakfast could have been better"

Reviewed on Jul 6, 2026

La Quinta Inn & Suites by Wyndham Lake George
See all 1,656 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 Vacations
All Inclusive Vacations
Beach Vacations
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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 does a Chestertown vacation package cost?
You'll find cheap prices from CA $1,345 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 many days is enough for Chestertown?
With a well-organized schedule, you can easily tick off the most popular Chestertown sights in a handful of days. But if you prefer to explore off the beaten track or go on day tours, think about booking your Chestertown vacation for longer.
Is it worth booking a vacation package to Chestertown?
It's easy to see why a Chestertown vacation is on the to-do list of many travellers. Leading attractions like Loon Lake Beach are just the start of things to see and do here.
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 travelling 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 favourite 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.