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Apartments in Chestertown

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, (69)
"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 AED 507
AED 1,114 total
includes taxes & fees
8 Oct - 9 Oct
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)
"Very clean, great location"
Bolton Landing - walk to town! Come visit any Season!

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 AED 1,102
AED 1,982 total
includes taxes & fees
15 Oct - 16 Oct
Huge Windows Downtown 2Bd Apt w/ Main Strip Access

Cozy Lakeside Apartment - 5 Min Walk to Downtown!

9.8 out of 10, Exceptional, (7)
"It was a Great location"
The price is AED 735
AED 1,313 total
includes taxes & fees
5 Oct - 6 Oct
Cozy Lakeside Apartment - 5 Min Walk to Downtown!

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, (30)
"Great getaway with a very homely touch, thank you Cheri"
The price is AED 386
AED 958 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

Unique Loft Downtown Glens Falls

9.0 out of 10, Wonderful, (2)
The price is AED 1,102
AED 2,096 total
includes taxes & fees
1 Nov - 2 Nov
Unique Loft Downtown Glens Falls

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

10.0 out of 10, Exceptional, (1)
"We loved everything about the apartment- it was in a great location, very clean, and had everything we needed. The pool was also amazing and the host was very responsive. The apartment was a quick 15-20 minutes from Lake George. Had a great time and would definitely stay there again!"
Stay on 80 acres close to Lake George w/shared pool, stables, bbq, RV parking

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 AED 459
AED 1,052 total
includes taxes & fees
8 Oct - 9 Oct
Gore Mountain Lift View, The Eagles Nest: 251 Main St, Fl 3

1-BR Gem Near Downtown & Nature Escapes

The price is AED 477
AED 1,013 total
includes taxes & fees
5 Oct - 6 Oct
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

Lakeview Suites

9.8 out of 10, Exceptional, (50)
"Great place"
Lakeview Suites

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

9.4 out of 10, Exceptional, (3)
"Good location for our needs and very private."
Cozy 1 bedroom efficiency in a forest-like setting near Lake George and Saratoga

Lake George Getaway with SAUNA!

10.0 out of 10, Exceptional, (9)
"Great customer service. Comfy bed"
Lake George Getaway with SAUNA!

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!

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

10.0 out of 10, Exceptional, (67)
"Location is great"
Lake view cozy two bedroom in Bolton Landing - walk to Town!

Recently renovated, country setting, short walk to town and beach

10.0 out of 10, Exceptional, (10)
"Comfortable, great location had everything we needed. Would definitely stay again. Communication with host was simple."
Recently renovated, country setting, short walk to town and 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.
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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. 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. Gore Mountain Lift View: North Creek Main St Apt 2: 9.8 mi/15.7 km away in North Creek. Amenities include private balconies. Gore Mountain Lift View, The Eagles Nest: 251 Main St, Fl 3: It's located in North Creek, 9.8 mi/15.7 km from Chestertown. Includes private balconies.
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.