Chestertown Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Julie Miller

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 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 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.

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.

Ready to book your vacation to Chestertown?

 

Choose your dates

Chestertown Hotel Deals

Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

2 out of 5
5537 State Route 8, Chestertown, NY
The price is CA $239 per night from Jul 23 to Jul 24
CA $239
CA $266 total
Jul 23 - Jul 24
includes taxes & fees
9.2/10 Wonderful! (129 reviews)
"Nice & quiet. The rooms were quaint & comfortable. Would return there to stay in the future."

Reviewed on Jul. 17, 2025

Pine Tree Motel & Cabins
Friends Lake Inn

Friends Lake Inn

4 out of 5
963 Friends Lake Rd, Chestertown, NY
The price is CA $305 per night from Jul 23 to Jul 24
CA $305
CA $339 total
Jul 23 - Jul 24
includes taxes & fees
8.8/10 Excellent! (90 reviews)
"We visited the Inn hotel to celebrate my husband’s birthday and take a much-needed break from my role as a caregiver for my mother. The weekend turned out to be exactly what we needed—it gave us the chance to unplug, recharge, and truly rest. The staff were friendly, accommodating, and just lovely ..."

Reviewed on Jun. 23, 2025

Friends Lake Inn
Best Western of Lake George

Best Western of Lake George

2.5 out of 5
2452 State Route 9N, Lake George, NY
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Jul 28 to Jul 29
CA $175
CA $195 total
Jul 28 - Jul 29
includes taxes & fees
7.8/10 Good! (1,012 reviews)
"There should be clarity upon checkin as it pertains to maid service for room. Room wasnt cleaned and had to request new towels. Guests using regular towels for pool which caused towel shortage for showers. Room was only cleaned once in 3 days and amenities were not replaced. Information should be ..."

Reviewed on Jul. 18, 2025

Best Western of Lake George
See all 1,555 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

Beach Vacations

Family Vacations

Family Vacations

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

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 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.

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