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Apartments in Chestertown

Our top choices for Chestertown apartments

Contemporary king w/futon

10.0 out of 10, Exceptional, (6)
"Beautiful place very convenient would stay again"
Contemporary king w/futon

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

10.0 out of 10, Exceptional, (68)
"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 525
SAR 1,146 total
includes taxes & fees
9 Sep - 10 Sep
Gore Mountain Lift View: North Creek Main St Apt 2

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

10.0 out of 10, Exceptional, (57)
"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!

Cozy Lakeside Apartment - 5 Min Walk to Downtown!

9.8 out of 10, Exceptional, (7)
"It was a Great location"
Cozy Lakeside Apartment - 5 Min Walk to Downtown!

Huge Windows Downtown 2Bd Apt w/ Main Strip Access

10.0 out of 10, Exceptional, (2)
"Great location with rustic touches and fully renovated"
The price is SAR 1,126
SAR 2,012 total
includes taxes & fees
12 Sep - 13 Sep
Huge Windows Downtown 2Bd Apt w/ Main Strip Access

Charming 2-bedroom apartment in delightful Lake George Village

10.0 out of 10, Exceptional, (2)
"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

Lily Pad North at Loon Lake near Gore Mountain

9.6 out of 10, Exceptional, (29)
"Stay was very niceGreat location. Had everything we needed and host was great. Quick responses to any questionsWould recommend to everyone "
The price is SAR 450
SAR 1,037 total
includes taxes & fees
6 Oct - 7 Oct
Lily Pad North at Loon Lake near Gore Mountain

Lake George Great Location with Lake Access

10.0 out of 10, Exceptional, (22)
"We had a pleasant stay enjoyed the host and surroundings"
Lake George Great Location with Lake Access

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

6.0 out of 10, (4)
"Very large with everything we needed.Fast communication.We enjoyed our stay."
The price is SAR 338
SAR 1,374 total
includes taxes & fees
9 Sep - 10 Sep
Charming Ground floor 2-bedroom apartment with WiFi, AC in tranquil Glens Falls

Unique Loft Downtown Glens Falls

9.0 out of 10, Wonderful, (2)
Unique Loft Downtown Glens Falls

Lakeview Suites

9.8 out of 10, Exceptional, (49)
"Great place"
Lakeview Suites

Stay on 80 acres close to Lake George w/shared pool, stables, bbq, RV parking

Stay on 80 acres close to Lake George w/shared pool, stables, bbq, RV parking

Cozy 1 bedroom efficiency in a forest-like setting near Lake George and Saratoga

10.0 out of 10, Exceptional, (2)
"Neat, clean and cozy in a forest-like setting as advertised!! Terrific host and location."
Cozy 1 bedroom efficiency in a forest-like setting near Lake George and Saratoga

1-BR Gem Near Downtown & Nature Escapes

1-BR Gem Near Downtown & Nature Escapes

Convenient 2-bedroom apartment in Glens Falls with WiFi

2.0 star property
10.0 out of 10, Exceptional, (4)
"The apartment was adorable. Very comfy and we had everything we needed. The owners are wonderful people, we really have no comlaints at all! "
Convenient 2-bedroom apartment in Glens Falls with WiFi

Lake George Getaway with SAUNA!

10.0 out of 10, Exceptional, (8)
"Great customer service. Comfy bed"
Lake George Getaway with SAUNA!

Gore Mountain Lift View, The Eagles Nest: 251 Main St, Fl 3

9.4 out of 10, Exceptional, (3)
"So close to Gore MT. Very clean and adorable!!"
The price is SAR 510
SAR 1,125 total
includes taxes & fees
30 Sep - 1 Oct
Gore Mountain Lift View, The Eagles Nest: 251 Main St, Fl 3

RIVERVIEW ADIRONDACK RUSTIC APARTMENT

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

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

10.0 out of 10, Exceptional, (51)
"Great stay, convenient location and walk to town, quite and clean"
Lake view , Cozy One Bedroom! Walk to Beach and Town!
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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Top Chestertown Hotel Reviews

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can choose from 7 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. Contemporary king w/futon: Located 21.1 mi/33.9 km away in Whitehall. Bolton Landing - walk to town! Come visit any Season!: It's located in Bolton Landing, 9.7 mi/15.6 km away. Lake George Great Location with Lake Access: Located 17 mi/27.3 km away in Lake George. Free WiFi and private patios are included. Access to onsite laundry facilities is available on site.
How many apartments will I be able to find in Chestertown?
Expedia has 7 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.