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Search Apartments in Chestertown

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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

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, (15)
"We had a pleasant stay enjoyed the host and surroundings"
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, (14)
"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!
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, (27)
"minimal communication with the host - no greeting when we arrived - would have been nice"
The price is AED 378
AED 890 total
includes taxes & fees
26 May - 27 May
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. "
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 1,313 total
includes taxes & fees
2 May - 3 May
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

10.0 out of 10, Exceptional, (11)
"10/10 on all counts. Clean, convenient, great accommodations, awesome location, A property manager. Kathleen is an ace, very good Will be visiting again in the future 100%"
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, (5)
"Great customer service. Comfy bed"
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!

9.4 out of 10, Exceptional, (6)
"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
Unique Loft Downtown Glens Falls
Interior

Unique Loft Downtown Glens Falls

The price is AED 1,102
AED 2,083 total
includes taxes & fees
1 May - 2 May
Unique Loft Downtown Glens Falls
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.
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Other property types in Chestertown

Camp Lillian Gorgeous New Cabin with Mountain Views
Outdoor dining

Camp Lillian Gorgeous New Cabin with Mountain Views

9.8 out of 10, Exceptional, (66)
"Very peaceful property with lovely views. We will definitely be back!"
The price is AED 514
AED 771 total
includes taxes & fees
1 May - 2 May
Camp Lillian Gorgeous New Cabin with Mountain Views
Trout House Village Resort
Luxury Cabin, 1 Bedroom, Lake View | Living area | 42-inch Smart TV with digital channels, DVD player, streaming services

Trout House Village Resort

3.0 star property
10.0 out of 10, Exceptional, (10)
"Absolutely wonderful place and super friendly staff "
The price is AED 531
AED 681 total
includes taxes & fees
1 May - 2 May
Trout House Village Resort
Walk to Million Dollar Beach from this awesome Cottage!
Exterior

Walk to Million Dollar Beach from this awesome Cottage!

10.0 out of 10, Exceptional, (151)
"This is our third time staying at this property. Each and every time, I am so sad to leave. The hosts are fantastic and answer promptly any questions we may have. This property is so beautiful and we can't wait to come back again next spring."
Walk to Million Dollar Beach from this awesome Cottage!
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?
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. Lily Pad South at Loon Lake near Gore Mountain: Located 3.7 mi/5.9 km away in Chestertown. 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. Lakefront Bolton Retreat w/ Balcony + Views!: 10.1 mi/16.2 km away in Bolton Landing. Private balconies and fireplaces are included. Modern Apt Near Lake George - Walk to Beach!: Located in Hague, 16.4 mi/26.4 km from Chestertown. Includes sofa beds. Access to onsite laundry facilities is available on site.
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.