Photo by Julie Miller

Search Apartments in Chestertown

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Compare 73 Apartments in Chestertown with updated reviews, rates, and availability.

Lake George Great Location with Lake Access
Property grounds

Lake George Great Location with Lake Access

10.0 out of 10, Exceptional, (13)
"We had a wonderful time. Everything was within walking distance. The place was very clean and adorable. We loved the little “extras” that was left for us. Would definitely stay there again. The host wash very friendly and gave us great restaurant ideas "
Lake George Great Location with Lake Access
Lake George Getaway w/ Mountain + Water Views
Marina

Lake George Getaway w/ Mountain + Water Views

10.0 out of 10, Exceptional, (8)
"Easy check in, clean unit, close to EVERYTHING! "
Lake George Getaway w/ Mountain + Water Views
Modern Apt Near Lake George - Walk to Beach!
Snow and ski sports

Modern Apt Near Lake George - Walk to Beach!

9.6 out of 10, Exceptional, (12)
"We had a lovely time during a long winter weekend after Christmas. There were a few places to choose from to take the kids sledding and we even enjoyed a winter hike. It was our first time this far NW in the Adirondacks and the scenery was gorgeous. Will be back! "
Modern Apt Near Lake George - Walk to Beach!
Lakefront Bolton Retreat w/ Balcony + Views!
Marina

Lakefront Bolton Retreat w/ Balcony + Views!

10.0 out of 10, Exceptional, (12)
"Exceeded expectations. Our 2 bedroom suite was very spacious. We noticed immediately that everything was very clean and up to date. It’s about two miles to the Bolton Landing Main Street and about 9-10 miles from the heart of Lake George village. Kathleen was awesome to work with "
Lakefront Bolton Retreat w/ Balcony + Views!
Gore Mountain Lift View: North Creek Main St Apt 2
Outdoor dining

Gore Mountain Lift View: North Creek Main St Apt 2

9.0 out of 10, Wonderful, (10)
"Place was great for the price. Clean and was easy to communicate with the owner. "
The price is AED 731
AED 1,380 total
includes taxes & fees
26 Mar - 27 Mar
Gore Mountain Lift View: North Creek Main St Apt 2
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (60)
"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
Lily Pad South at Loon Lake near Gore Mountain
Outdoor dining

Lily Pad South at Loon Lake near Gore Mountain

9.8 out of 10, Exceptional, (47)
"The property was very clean and well supplied. We used it as our home base to snow tube nearby. "
Lily Pad South at Loon Lake near Gore Mountain
Lake view cozy two bedroom in Bolton Landing - walk to Town!
Beach

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

10.0 out of 10, Exceptional, (61)
"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!
Lily Pad North at Loon Lake near Gore Mountain
Outdoor dining

Lily Pad North at Loon Lake near Gore Mountain

9.8 out of 10, Exceptional, (26)
"minimal communication with the host - no greeting when we arrived - would have been nice"
Lily Pad North at Loon Lake near Gore Mountain
Bubar Barn - screen porch, deck, + parking
Terrace/patio

Bubar Barn - screen porch, deck, + parking

10.0 out of 10, Exceptional, (9)
"Came to ski, perfect spot for 2 dads and three teenage boys. "
The price is AED 588
AED 1,113 total
includes taxes & fees
1 Apr - 2 Apr
Bubar Barn - screen porch, deck, + parking
Mid-Century Modern Apt - Steps to Lake George
Fridge, microwave, stovetop, coffee/tea maker

Mid-Century Modern Apt - Steps to Lake George

9.6 out of 10, Exceptional, (9)
"Conveniently located near Lake George Open Water Swim. Clean and neat. Nice to have The Hague market nearby as well. "
Mid-Century Modern Apt - Steps to Lake George
RIVERVIEW ADIRONDACK RUSTIC APARTMENT
Terrace/patio

RIVERVIEW ADIRONDACK RUSTIC APARTMENT

7.8 out of 10, Good, (6)
"We had another VRBO but 4 hours before check in we were canceled on because of the recent storm that made the property unavailable. We last minute booked this property & we were grateful to find a place last minute. We asked if we could check in early which the host accommodated but they provided no further details so we ultimately ended up showing up at the property because we couldn’t reach the owner through the app. The host was staying at the property the night before & left food in the...
RIVERVIEW ADIRONDACK RUSTIC APARTMENT
Cozy Lakeside Apartment - 5 Min Walk to Downtown!
2 bedrooms, free WiFi, bed sheets

Cozy Lakeside Apartment - 5 Min Walk to Downtown!

9.8 out of 10, Exceptional, (7)
" "
The price is AED 735
AED 1,297 total
includes taxes & fees
26 Mar - 27 Mar
Cozy Lakeside Apartment - 5 Min Walk to Downtown!
Bolton Landing Suite w/ Deck, Lake George Access
Marina

Bolton Landing Suite w/ Deck, Lake George Access

9.8 out of 10, Exceptional, (9)
"The property owners were very communicative and the information at the house is excellent about things to do."
Bolton Landing Suite w/ Deck, Lake George Access
Lake George Getaway with SAUNA!
Property grounds

Lake George Getaway with SAUNA!

10.0 out of 10, Exceptional, (4)
"Perfect for a small weekend getaway for a couple - it's close to the village, it's clean, it's warm, and there are plenty of things to use at your convenience (e.g. pots, pans, paper towel, paper plates, Jenga). Someone lives upstairs and you can hear footsteps and other noises when they are home but they were barely home when we were there so it was not an issue for us. "
Lake George Getaway with SAUNA!
Lake view , Cozy One Bedroom! Walk to Beach and Town!
1 bedroom, WiFi, bed sheets

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

10.0 out of 10, Exceptional, (45)
"Great property very clean and close to the lake. Host had excellent communication. We will be staying here again in the future."
Lake view , Cozy One Bedroom! Walk to Beach and Town!
Bolton Landing - walk to town! Come visit any Season!
Beach

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

9.8 out of 10, Exceptional, (49)
"This was our second time staying at this property. It was perfect. "
Bolton Landing - walk to town! Come visit any Season!
Lakefront Adirondacks Home: Fish, Hike, Ski!
Marina

Lakefront Adirondacks Home: Fish, Hike, Ski!

9.2 out of 10, Wonderful, (5)
"The perfect long weekend getaway! Loved waking up to the views (especially seeing the ice fishing out on the lake). The guide was especially helpful, because we found wonderful hiking trails only minutes from the house. Would definitely recommend to family and friends! "
Lakefront Adirondacks Home: Fish, Hike, Ski!
Convenient 2-bedroom apartment in Glens Falls with WiFi
Private kitchen

Convenient 2-bedroom apartment in Glens Falls with WiFi

2.0 star property
10.0 out of 10, Exceptional, (2)
"The place was cozy. Easy check in and out process. Great place to stay."
Convenient 2-bedroom apartment in Glens Falls with WiFi
Contemporary king w/futon
Shower, hair dryer, towels, soap

Contemporary king w/futon

10.0 out of 10, Exceptional, (2)
"Very nice stay clean neat and new"
Contemporary king w/futon
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.
Don't see what you're looking for?
See all available properties in Chestertown
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chestertown

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (60)
"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
Lakefront cabin with beautiful loft, game room, views, private dock
Exterior

Lakefront cabin with beautiful loft, game room, views, private dock

9.2 out of 10, Wonderful, (36)
"Plenty of room for everyone, warm and relaxing."
Lakefront cabin with beautiful loft, game room, views, private dock
Year round Log Cabin on Loon Lake. Minutes from skiing at Gore Mountain
Interior

Year round Log Cabin on Loon Lake. Minutes from skiing at Gore Mountain

9.8 out of 10, Exceptional, (84)
"Wonderful stay. Owner very accomodating. We had everything we needed."
Year round Log Cabin on Loon Lake. Minutes from skiing at Gore Mountain
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.

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can choose from 8 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.
What's the best apartment for my stay in Chestertown?
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George: Includes free WiFi, private patios, and fireplaces. Lily Pad North at Loon Lake near Gore Mountain: Includes laundry facilities and private patios.
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.