Chestertown Vacations from $448

Book a Hotel + Flight or Car together to unlock savings

Photo by Julie Miller

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.

The Latest Chestertown vacation packages

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn Queensbury

Red Roof Inn Queensbury

2.5 out of 5
Price was $487, price is now $448 per person
$448
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Glens Falls (GFL)
7/10 Good! (1,000 reviews)
this hotel was a last-minute book, and I would never again. although the staff was nice the hotel looked like it was thrown together with spare parts. the first room had a dirty bathroom the toilet had a ring around the bowl, hair in the sing and the tub was filthy. the room I switched to has a room door that didn't touch the ground, so you heard everything that was going on in the hallway. also, I'm not sure if people live there but there was a smell of cat urine in the hallway. thankffully it was only 1 night.

Reviewed on Nov 24, 2025

The Fern Lodge

The Fern Lodge

3.5 out of 5
Price was $1,327, price is now $1,118 per person
$1,118
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Glens Falls (GFL)
9.8/10 Exceptional! (50 reviews)
Absolutely beautiful

Reviewed on Oct 22, 2025

Days Inn by Wyndham Queensbury/Lake George

Days Inn by Wyndham Queensbury/Lake George

2 out of 5
Price was $500, price is now $456 per person
$456
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Glens Falls (GFL)
5.6/10 (1,000 reviews)
Hotel is old. I can see that they are trying. So that’s why I give them a 3 rating. But there was no hairdryer, and come on some kind of curtains on the window would have been nice. Yep it did have a shade, but I was on the first floor and you pull shade. It is very dark in the middle of the day would’ve liked some sunshine.. Checked out at 8 AM and what you consider breakfast was a joke. There was a handful of granola bars and a couple pieces of white bread. No tables no chairs. I don’t even know if there was coffee? sure did not see any juices. But the heater/air was quite enough. So if you just need to go and sleep and get up and leave it did its job.

Reviewed on Oct 20, 2025

Fairfield Inn & Suites by Marriott Queensbury Glens Falls/Lake George Area

Fairfield Inn & Suites by Marriott Queensbury Glens Falls/Lake George Area

2.5 out of 5
Price was $578, price is now $542 per person
$542
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Glens Falls (GFL)
9.6/10 Exceptional! (462 reviews)
Clean room! Great staff! Excellent stay!

Reviewed on Nov 3, 2025

The Queensbury Hotel

The Queensbury Hotel

3 out of 5
Price was $563, price is now $534 per person
$534
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Glens Falls (GFL)
9.4/10 Exceptional! (1,423 reviews)
Wonderful hotel, with lots of old charm!

Reviewed on Nov 26, 2025

Don't see what you're looking for?
See all available trips from Columbus to Chestertown
View all trips

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now

Discover the most popular places to visit in Chestertown

Loon Lake Beach

If a restful vacation is part of your travel plans, Loon Lake Beach might be the perfect place to seek out during your trip to Chestertown. While you're in the area, stroll along the lakeside.

Loon Lake Beach

Chestertown Hotel Deals

Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

2 out of 5
5537 State Route 8 Chestertown NY
9.2/10 Wonderful! (146 reviews)
We attended the Warrensburg Largest Garage Sale Weekend. The Motel is only 20 minutes away from the event. Located near Chestertown so you can go out to eat or grab groceries at the local Grocery Store. Motel is Dog Friendly and we did not have any issues with the Wi-Fi.

Reviewed on Oct 5, 2025

Get rates
Pine Tree Motel & Cabins
Friends Lake Inn

Friends Lake Inn

4 out of 5
963 Friends Lake Rd Chestertown NY
8.6/10 Excellent! (102 reviews)
Staff was great. The inn is unique. Perfect!

Reviewed on Sep 7, 2025

Get rates
Friends Lake Inn
The Fern Lodge

The Fern Lodge

3.5 out of 5
46 Fiddlehead Bay Rd. Chestertown NY
$512 nightly
The price is $569 total per night from Dec 1 to Dec 2
$569 total
Dec 1 - Dec 2
Total with taxes and fees
9.8/10 Exceptional! (45 reviews)
Absolutely beautiful

Reviewed on Oct 22, 2025

The Fern Lodge
See all 1,536 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.

Find the Best Chestertown Vacation Packages

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 2 miles (3 km) from the downtown area.

Chestertown Essential Information

Language
English
Currency
U.S dollars
Population
680
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Gore Mountain Ski Resort, Loon Lake Beach and Natural Stone Bridge and Caves

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chestertown vacation package cost?
You can snap up a vacation package to this destination from $448 on Expedia. But how much your vacation to Chestertown costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Chestertown?
If you're looking to book a cheap Chestertown vacation package, consider visiting in February, November and December. You're likely to find lower rates on hotels and flights during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Chestertown?
The ideal duration of your Chestertown vacation depends on what you'd like to see and do. Usually, a few days to a week will give you enough time to hit all the top sights and explore some hidden gems along the way.
Is it worth booking a vacation package to Chestertown?
Chestertown is a good vacation destination with attractions like Loon Lake Beach among the many things to keep you entertained. Whether you're heading away with the family or planning a trip with friends, a Chestertown vacation promises a good time for everyone.
How to find the best Chestertown package deals?
Use Expedia's filter tool to find some tempting Chestertown package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Chestertown package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Chestertown vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component separately. And you'll still enjoy the flexibility to create a personalized Chestertown vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Chestertown?
Enjoy incredible discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Chestertown vacation.
Does Expedia offer Book Now, Pay Later Chestertown vacation packages?
If you're like us, you love going away but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Chestertown trip over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.