A waterfront town with a pier, dock, and several buildings.

Search Apartments in Chestertown

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Chestertown apartments

A sandy beach with a calm lake, trees, and a distant hill.

1. Schroon Lake Room < 1 Mi to Marina & Beach!

Schroon Lake Room < 1 Mi to Marina & Beach!
3.0 star property
Schroon Lake
10.0 out of 10, Exceptional, (1 review)
"Clean, comfortable room. Very friendly and welcoming hosts."
United States
Kevin
The price is ₩186,851
₩229,854 total
includes taxes & fees
Oct 29 - Oct 30
Schroon Lake Room < 1 Mi to Marina & Beach!
A beach with a stone wall, trees, and a clear sky.

2. Close to Marina, Beach & Town! Schroon Lake Escape

Close to Marina, Beach & Town! Schroon Lake Escape
3.0 star property
Schroon Lake
The price is ₩187,480
₩230,628 total
includes taxes & fees
Oct 1 - Oct 2
Close to Marina, Beach & Town! Schroon Lake Escape
A beach with a stone wall, trees, and a calm lake.

3. Cozy Room Near Schroon Lake Marina, Town & Beach!

Cozy Room Near Schroon Lake Marina, Town & Beach!
3.0 star property
Schroon Lake
6.0 out of 10, (2 reviews)
"Help!! We didn’t stay at this property due to the property stating it was lakefront and marina. The property was in complete disrepair condition. Junk cars, high weeds, room smelled of smoke. I would request a refund."
United States
Pamela
The price is ₩186,851
₩229,854 total
includes taxes & fees
Oct 7 - Oct 8
Cozy Room Near Schroon Lake Marina, Town & Beach!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites

8/10 Good
"The hotel is very well located, and the price-to-value ratio is excellent. The room was clean and comfortable, and the front desk staff was very friendly and helpful. The only minor inconvenience was the parking. The parking area was quite full, so we had to park in a spot that was a little far from our room. However, the parking was still within the hotel property, so it was not a major issue. Overall, we had a very pleasant stay and would definitely consider staying here again."
Maria 1-night trip
Posted 4 hours ago
Adirondack Retreat Inn & Suites

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
3
Accommodation
19 Apartments
Lowest Price
₩229,854
Highest Price
₩230,628

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can choose from 5 apartments in Chestertown for your stay. Why not take time to appreciate the lakeside during your visit?
Why would you choose an apartment versus a traditional hotel?
Often offering more space than a traditional hotel room, an apartment comes equipped with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home but also for couples who want something in a quieter part of town.
How many apartments will I be able to find in Chestertown?
Expedia has 5 apartments to book in Chestertown.
What will the weather be like during my trip to Chestertown?
Though weather is just one factor, it can really affect your travel plans, especially if you are planning a longer stay in Chestertown. 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 should I see in Chestertown?
Chestertown is known for its lakeside. Loon Lake Beach and Friends Lake are a couple of lovely local spots to get outside and enjoy nature. Loon Lake and Hudson River are other places to visit while you're in town.
What's the best way to get to and around Chestertown?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Glens Falls, NY (GFL-Floyd Bennett Memorial), which is located 23.6 mi (38 km) away from the city center. If you'd like to venture out around the area, consider renting a car to take in more sights.