Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Chestertown apartments

Interior

Walk to Schroon Lake! Studio w/ Shared Fire Pit

Walk to Schroon Lake! Studio w/ Shared Fire Pit
3.0 star property
Schroon Lake
The price is AED 404
AED 622 total
includes taxes & fees
26 Jun - 27 Jun
Walk to Schroon Lake! Studio w/ Shared Fire Pit
Outdoor dining

Gore Mountain Lift View: North Creek Main St Apt 2

Gore Mountain Lift View: North Creek Main St Apt 2
North Creek
9.0 out of 10, Wonderful, (10 reviews)
"Great location… Enjoyed our stay"
United States
Lynda N.
The price is AED 345
AED 882 total
includes taxes & fees
2 Jul - 3 Jul
Gore Mountain Lift View: North Creek Main St Apt 2
Exterior detail

Penthouse w/ Best Mtn Views Walk to Gore, Main St | Fast WiFi | Sleeps 6

Penthouse w/ Best Mtn Views Walk to Gore, Main St | Fast WiFi | Sleeps 6
North Creek
9.6 out of 10, Exceptional, (5 reviews)
"Clean, convenient, and lots of space for the three of us. "
United States
Michael
The price is AED 455
AED 1,021 total
includes taxes & fees
2 Jul - 3 Jul
Penthouse w/ Best Mtn Views Walk to Gore, Main St | Fast WiFi | Sleeps 6
Fridge, microwave, oven, stovetop

Hip Suite-1st Floor - Arts District/Farmers Mkt/Cafes/Breweries-Near Lake George

Hip Suite-1st Floor - Arts District/Farmers Mkt/Cafes/Breweries-Near Lake George
Glens Falls
9.8 out of 10, Exceptional, (6 reviews)
"Clean, well appointed, full kitchen supplies, great location!"
United States
Lauren T.
The price is AED 474
AED 1,211 total
includes taxes & fees
29 Jun - 30 Jun
Hip Suite-1st Floor - Arts District/Farmers Mkt/Cafes/Breweries-Near Lake George
Dining

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

Charming Ground floor 2-bedroom apartment with WiFi, AC in tranquil Glens Falls
Glens Falls
6.4 out of 10, (5 reviews)
"Very large with everything we needed.Fast communication.We enjoyed our stay."
Canada
Mathieu T.
The price is AED 544
AED 787 total
includes taxes & fees
21 Jul - 22 Jul
Charming Ground floor 2-bedroom apartment with WiFi, AC in tranquil Glens Falls
2 bedrooms, free WiFi, bed sheets

Cozy Lakeside Apartment - 5 Min Walk to Downtown!

Cozy Lakeside Apartment - 5 Min Walk to Downtown!
Schroon Lake
9.8 out of 10, Exceptional, (7 reviews)
"Adorable and well kept"
United States
Marci B.
The price is AED 735
AED 1,317 total
includes taxes & fees
29 Jun - 30 Jun
Cozy Lakeside Apartment - 5 Min Walk to Downtown!
Outdoor dining

Walk to Schroon Lake! Studio w/ Shared Fire Pit

Walk to Schroon Lake! Studio w/ Shared Fire Pit
Schroon Lake
The price is AED 364
AED 631 total
includes taxes & fees
26 Jun - 27 Jun
Walk to Schroon Lake! Studio w/ Shared Fire Pit
Beach nearby

Easy Schroon Lake Living! Close to Marina & Town

Easy Schroon Lake Living! Close to Marina & Town
Schroon Lake
The price is AED 364
AED 631 total
includes taxes & fees
28 Jun - 29 Jun
Easy Schroon Lake Living! Close to Marina & Town
Beach nearby

Schroon Lake Room < 1 Mi to Marina & Beach!

Schroon Lake Room < 1 Mi to Marina & Beach!
Schroon Lake
The price is AED 364
AED 631 total
includes taxes & fees
29 Jun - 30 Jun
Schroon Lake Room < 1 Mi to Marina & Beach!
Beach

Close to Marina, Beach & Town! Schroon Lake Escape

Close to Marina, Beach & Town! Schroon Lake Escape
Schroon Lake
The price is AED 364
AED 631 total
includes taxes & fees
26 Jun - 27 Jun
Close to Marina, Beach & Town! Schroon Lake Escape
Apartment (0 Bedroom) | Interior

Schroon Lake Room < 1 Mi to Marina & Beach!

Schroon Lake Room < 1 Mi to Marina & Beach!
3.0 star property
Schroon Lake
The price is AED 404
AED 622 total
includes taxes & fees
29 Jun - 30 Jun
Schroon Lake Room < 1 Mi to Marina & Beach!
Beach nearby

Boat, Fish & Hike! All-Season Schroon Lake Getaway

Boat, Fish & Hike! All-Season Schroon Lake Getaway
Schroon Lake
The price is AED 364
AED 631 total
includes taxes & fees
26 Jun - 27 Jun
Boat, Fish & Hike! All-Season Schroon Lake Getaway
Interior

Unique Loft Downtown Glens Falls

Unique Loft Downtown Glens Falls
glens falls
9.4 out of 10, Exceptional, (3 reviews)
"Very convenient location, very clean. Such a cool place to stay. Very happy with everything. "
United States
Michael A.
The price is AED 1,102
AED 2,096 total
includes taxes & fees
27 Jun - 28 Jun
Unique Loft Downtown Glens Falls
2 bedrooms, bed sheets

Huge Windows Downtown 2Bd Apt w/ Main Strip Access

Huge Windows Downtown 2Bd Apt w/ Main Strip Access
Glens Falls
10.0 out of 10, Exceptional, (2 reviews)
"Great location with rustic touches and fully renovated"
United States
Brian H.
The price is AED 1,102
AED 1,969 total
includes taxes & fees
28 Jun - 29 Jun
Huge Windows Downtown 2Bd Apt w/ Main Strip Access
Beach nearby

Cozy Room Near Schroon Lake Marina, Town & Beach!

Cozy Room Near Schroon Lake Marina, Town & Beach!
Schroon Lake
The price is AED 364
AED 631 total
includes taxes & fees
29 Jun - 30 Jun
Cozy Room Near Schroon Lake Marina, Town & Beach!
Beach nearby

Boat, Fish, Hike! Schroon Lake Getaway

Boat, Fish, Hike! Schroon Lake Getaway
Schroon Lake
The price is AED 404
AED 677 total
includes taxes & fees
29 Jun - 30 Jun
Boat, Fish, Hike! Schroon Lake Getaway
Beach

< 1 Mi to Boat Launch! Schroon Lake Basecamp

< 1 Mi to Boat Launch! Schroon Lake Basecamp
Schroon Lake
10.0 out of 10, Exceptional, (1 review)
"Great room, very clean and cozy."
United States
Guy P.
The price is AED 404
AED 677 total
includes taxes & fees
29 Jun - 30 Jun
< 1 Mi to Boat Launch! Schroon Lake Basecamp
Game room

Gore Mountain Lift View Ski Apt: Main St 1&2 Combo

Gore Mountain Lift View Ski Apt: Main St 1&2 Combo
North Creek
The price is AED 804
AED 1,809 total
includes taxes & fees
26 Jun - 27 Jun
Gore Mountain Lift View Ski Apt: Main St 1&2 Combo
Apartment (0 Bedroom) | Interior

Close to Marina, Beach & Town! Schroon Lake Escape

Close to Marina, Beach & Town! Schroon Lake Escape
3.0 star property
Schroon Lake
The price is AED 404
AED 622 total
includes taxes & fees
29 Jun - 30 Jun
Close to Marina, Beach & Town! Schroon Lake Escape
Apartment (0 Bedroom) | Interior

Easy Schroon Lake Living! Close to Marina & Town

Easy Schroon Lake Living! Close to Marina & Town
3.0 star property
Schroon Lake
The price is AED 404
AED 622 total
includes taxes & fees
29 Jun - 30 Jun
Easy Schroon Lake Living! Close to Marina & 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

The Georgian Lakeside Resort

The Georgian Lakeside Resort

10/10 Excellent
"Room was clean and staff was friendly "
Laura 1-night trip
Posted less than an hour ago
The Georgian Lakeside Resort

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can search through 5 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. Lake view , Cozy One Bedroom! Walk to Beach and Town!: Located 9.7 mi/15.6 km away in Bolton Landing. Lake George Perfect Location with Lakefront Access & View of Summer Fireworks: 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. Lakeview Suites: 10 mi/16.2 km away in Bolton Landing. Private patios and fireplaces are included.
How many apartments will I be able to find in Chestertown?
Expedia has 5 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. Hudson River and Loon Lake 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.