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Cheap Hotels in Chestertown, NY from $248

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Check availability on Chestertown Cheap Hotels

Tonight
Oct 7 - Oct 8
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Oct 8 - Oct 9
This weekend
Oct 10 - Oct 12
Next weekend
Oct 17 - Oct 19

Top Chestertown Cheap Hotels

Friends Lake Inn
Premier Room | 1 bedroom, premium bedding, individually decorated

Friends Lake Inn

4.0 star property
8.6 out of 10, Excellent, (102)
"Staff was great. The inn is unique. Perfect!"
$223 nightly
The price is $248
Oct 8 - Oct 9
Total with taxes and fees
Friends Lake Inn
The Fern Lodge
Lake view

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (47)
"Comfortable, friendly, beautiful lodge, spacious facilities"
$507 nightly
The price is $563
Nov 3 - Nov 4
Total with taxes and fees
The Fern Lodge
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.
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Find out more about Chestertown

Find out more about Chestertown

How can I get cheap hotels in Chestertown?

Best tips to find a cheap hotel in Chestertown

  1. If you're looking to travel to Chestertown on a budget, you'll be happy to know that you can find hotels for as low as $248. Of course, that price is affected by amenities, star rating, and even the time of year you visit. At most, hotel prices can be as high as $563. Staying a short amount of time in Chestertown is an effective way to reduce hotel costs.

  2. When you cut your vacation down to just a few days, you don't have to worry as much about hotel prices since you don't have that many nights to stay. For budget hotels in Chestertown, 3 to 4 days should be all the nights you need. That's generally enough to enjoy the city's top attractions, though there's certainly enough to do to warrant a week-long trip.

  3. When booking cheap hotel rooms in Chestertown, it's typically best to book about 3 weeks in advance. Book further in advance than that and you could be paying too much for your room, as hotels will often overestimate future demand. However, if you wait too long, you might find that the hotel has been completely booked.

  4. When you utilize search filters on Expedia, you'll be able to narrow down your results in a flash. These search filters cover a wide variety of factors you may be interested in when it comes to finding a cheap hotel in Chestertown, including amenities such as Free Breakfast, 2-star rating, or proximity to local attractions. You can even set filters for price limits to ensure that all the displayed results are within your budget.

Top Chestertown Hotel Reviews

Lakefront Terrace Resort

Lakefront Terrace Resort

10/10 Excellent
"Clean room with amazing views! Such a unique style building with outdoor hallways"
Sydney 1-night trip
Posted 13 hours ago
Lakefront Terrace Resort

Frequently asked questions

What is Chestertown like for travelers on a budget?
Chestertown offers cheap accommodation options and a variety of places to visit, making it a great getaway spot for budget travelers. You can find ways to save money while getting to know this destination, which is home to attractions like Loon Lake Beach, Friends Lake, and Loon Lake.
When is the best time for a budget trip to Chestertown?
Weather is probably a major factor when you plan your trip to Chestertown, and keep in mind that cheaper options are usually available when the weather isn't as good. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chestertown are January, March, November, and December, with each month seeing an average of 13 inches of snowfall.
What is there to see and do in Chestertown?
Chestertown is known for its lake views and offers things to see and do without spending a fortune. You can budget for the local attractions that interest you most, and then fill your itinerary with activities that cost little or nothing at all. Enjoy the outdoors at Loon Lake Beach and Friends Lake, or check out the area's cultural spots like Tannery Pond Community Center.
How can I get to Chestertown and get around on a budget?
Scoping out the transportation options in Chestertown is a smart way to keep your trip affordable. The closest airport is Glens Falls, NY (GFL-Floyd Bennett Memorial), situated 23.6 mi (38 km) away. Chestertown might not have very many public transportation choices so a car rental could be an economical alternative to see more of the area.

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