Photo by Julie Miller

Search Apartments in Chestertown

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Apartments in Chestertown

Charming Ground floor 2-bedroom apartment with WiFi, AC in tranquil Glens Falls

6.0 out of 10, (2)
"Very large with everything we needed.Fast communication.We enjoyed our stay."
The price is SAR 304
SAR 1,083 total
includes taxes & fees
3 Aug - 4 Aug
Charming Ground floor 2-bedroom apartment with WiFi, AC in tranquil Glens Falls

Bolton Landing - walk to town! Come visit any Season!

10.0 out of 10, Exceptional, (51)
"Such a great stay. Everything was clean and the location was perfect. The communication was also fantastic…will stay here again!"
Bolton Landing - walk to town! Come visit any Season!

Lake view cozy two bedroom in Bolton Landing - walk to Town!

10.0 out of 10, Exceptional, (62)
"Great space for our family and dog. Within walking distance to everything we needed during our Winter Carnival visit. Anna is a great host!"
Lake view cozy two bedroom in Bolton Landing - walk to Town!

Lake view , Cozy One Bedroom! Walk to Beach and Town!

10.0 out of 10, Exceptional, (46)
"Great stay, convenient location and walk to town, quite and clean"
Lake view , Cozy One Bedroom! Walk to Beach and Town!

Contemporary Queen with sofa sleeper

Contemporary Queen with sofa sleeper

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

10.0 out of 10, Exceptional, (62)
"My family and i had a great time here! The place is Amazing and we would definitely stay again! "
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

Gore Mountain Lift View: North Creek Main St Apt 2

9.0 out of 10, Wonderful, (10)
"Great location… Enjoyed our stay"
The price is SAR 394
SAR 978 total
includes taxes & fees
30 Jul - 31 Jul
Gore Mountain Lift View: North Creek Main St Apt 2

Contemporary king w/futon

10.0 out of 10, Exceptional, (4)
"Stayed two nights with my husband, mom, and our dog. This was a good location for us to go to the food and wine festival in Lake George. It was clean, peaceful and had all we needed. Communication from host was great. Definitely plan to stay here again."
Contemporary king w/futon

Mid-Century Modern Apt - Steps to Lake George

9.8 out of 10, Exceptional, (11)
"I enjoyed my stay very much to bad I had to work every day and I could not spen more time site seeing"
Mid-Century Modern Apt - Steps to Lake George

Lake George Great Location with Lake Access

10.0 out of 10, Exceptional, (18)
"We had a pleasant stay enjoyed the host and surroundings"
Lake George Great Location with Lake Access

Unique Loft Downtown Glens Falls

The price is SAR 1,125
SAR 2,140 total
includes taxes & fees
19 Aug - 20 Aug
Unique Loft Downtown Glens Falls

Charming 2-bedroom apartment in delightful Lake George Village

10.0 out of 10, Exceptional, (1)
"Hostess and her family extremely friendly and inviting! Always making sure we had what we needed. The property was beautiful and welcoming! Well definitely stay there again!!"
Charming 2-bedroom apartment in delightful Lake George Village

RIVERVIEW ADIRONDACK RUSTIC APARTMENT

7.8 out of 10, Good, (6)
"Thank you, stay-was welcoming.."
RIVERVIEW ADIRONDACK RUSTIC APARTMENT

Cozy Lakeside Apartment - 5 Min Walk to Downtown!

9.8 out of 10, Exceptional, (7)
"It was a Great location"
The price is SAR 780
SAR 1,381 total
includes taxes & fees
18 Aug - 19 Aug
Cozy Lakeside Apartment - 5 Min Walk to Downtown!

Modern Apt Near Lake George - Walk to Beach!

9.6 out of 10, Exceptional, (13)
"Great location and nice stay"
Modern Apt Near Lake George - Walk to Beach!

Lily Pad North at Loon Lake near Gore Mountain

9.6 out of 10, Exceptional, (29)
"Great getaway with a very homely touch, thank you Cheri"
Lily Pad North at Loon Lake near Gore Mountain

Lakefront Bolton Retreat w/ Balcony + Views!

10.0 out of 10, Exceptional, (20)
"Had an amazing time! Great, peaceful location with a beautiful view. Super close to stores and restaurants! Will definitely be coming back!"
Lakefront Bolton Retreat w/ Balcony + Views!

Convenient 2-bedroom apartment in Glens Falls with WiFi

2.0 star property
10.0 out of 10, Exceptional, (2)
"The couple who hosted are absolutely wonderful. We were the first one to stay. Everything was great. "
Convenient 2-bedroom apartment in Glens Falls with WiFi

Lakeview Suites

9.8 out of 10, Exceptional, (48)
"Great place"
Lakeview Suites

Lake George Getaway with SAUNA!

10.0 out of 10, Exceptional, (6)
"Great customer service. Comfy bed"
Lake George Getaway with SAUNA!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chestertown Hotel Reviews

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can search through 8 apartments in Chestertown for your stay. Take time during your trip to appreciate the lakeside, and discover the area's popular sights like Lake George.
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.
What's the best apartment for my stay in Chestertown?
Below are some of the top apartments in the area: Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George: Includes free WiFi, private patios, and fireplaces. Access to onsite laundry facilities is available on site. Charming Ground floor 2-bedroom apartment with WiFi, AC in tranquil Glens Falls: Located 24.4 mi/39.3 km away in Glens Falls. Fireplaces and Smart TVs are included. Onsite laundry facilities and a water park are on site. Lake George Great Location with Lake Access: Located in Lake George, 17 mi/27.3 km away. Includes free WiFi and private patios. Access to onsite laundry facilities is available on site. Bolton Landing - walk to town! Come visit any Season!: 9.7 mi/15.6 km away in Bolton Landing. Lake view , Cozy One Bedroom! Walk to Beach and Town!: It's situated in Bolton Landing, 9.7 mi/15.6 km from Chestertown.
How many apartments will I be able to find in Chestertown?
Expedia has 8 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.