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Compare 61 Apartments in Chestertown with updated reviews, rates, and availability.

Lily Pad South at Loon Lake near Gore Mountain

9.8 out of 10, Exceptional, (44)
"Very clean, comfortable, kitchen is well stocked with cookware & spices, lots of towels & crisp fresh sheets. 2 nice restaurants (Bull house & OP Fredericks) are within a few minutes drive. There is a LOT of outdoor firewood & we enjoyed relaxing by the fire pit."
Lily Pad South at Loon Lake near Gore Mountain

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 SAR 746
SAR 1,409 total
includes taxes & fees
9 Feb - 10 Feb
Gore Mountain Lift View: North Creek Main St Apt 2

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

10.0 out of 10, Exceptional, (57)
"Incredible place and stay, highly recommended!"
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

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 SAR 600
SAR 1,144 total
includes taxes & fees
10 Feb - 11 Feb
Bubar Barn - screen porch, deck, + parking

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!

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

10.0 out of 10, Exceptional, (60)
"We had a great time during our stay. The property was clean, spacious and conveniently located near the town and beach. Great hosts who were responsive and detail oriented. They literally thought of everything. Thanks for a wonderful week! "
Lake view cozy two bedroom in Bolton Landing - walk to Town!

Cozy Lakeside Apartment - 5 Min Walk to Downtown!

9.8 out of 10, Exceptional, (7)
" "
The price is SAR 750
SAR 1,324 total
includes taxes & fees
10 Feb - 11 Feb
Cozy Lakeside Apartment - 5 Min Walk to Downtown!

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

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

Lake George Great Location with Lake Access

10.0 out of 10, Exceptional, (12)
"Right next to the lake!"
Lake George Great Location with Lake Access

Bolton Landing Suite w/ Deck, Lake George Access

9.8 out of 10, Exceptional, (9)
"Fabulous location, Bolton Landing is picturesque and convenient to hiking and getting out on the lake...amazing autumn views"
Bolton Landing Suite w/ Deck, Lake George Access

Lake George Getaway with SAUNA!

10.0 out of 10, Exceptional, (3)
"Home is walking distance to Village and Tolley pickup right in front. Ali communication was clear and detailed. She also was quick to respond to any questions. P.S. You can use the Dumpster across the street at the hotel called Adirondack Sunrise if needed! 😊"
Lake George Getaway with SAUNA!

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!

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

9.0 out of 10, Wonderful, (2)
"This was a cute unit. It’s an older property so everything creeks, but part of the charm. Very very noisy people on the second floor, but that wasn’t the rental companies fault. Rate was good, but fees were extremely high. I’ve never seen the fees higher than the nightly rate and I use VRBO all the time. "
The price is SAR 746
SAR 1,409 total
includes taxes & fees
9 Feb - 10 Feb
Gore Mountain Lift View, The Eagles Nest: 251 Main St, Fl 3

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

10.0 out of 10, Exceptional, (10)
"Updated unit with two separate bedrooms. About 20 second drive from Cate’s Italian Garden. Host are just next door in the building of their own. Mary responds to messages almost immediately. Overall great stay. "
Recently renovated, country setting, short walk to town and beach

Lakefront Bolton Retreat w/ Balcony + Views!

10.0 out of 10, Exceptional, (11)
"We came here with our adult children for a long weekend. The property was very nice, but getting instructions to check in was very delayed. We were about an hour from the property and I had to send an email requesting information. You don’t get the “host”, this property is managed through a property management company, so specific property questions were diverted. Otherwise, I would recommend this property if you don’t mind spending a bit more. The condo is extremely spacious and the view from...
Lakefront Bolton Retreat w/ Balcony + Views!

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

9.8 out of 10, Exceptional, (48)
"We have stayed in every unit at this property and love ever single one. Anna is so responsive and the unit always feels like we are at home. Absolutely the best!!!!!!!"
Bolton Landing - walk to town! Come visit any Season!

Cozy One Bedroom studio suite in idyllic Adirondack setting

10.0 out of 10, Exceptional, (40)
"I thoroughly enjoyed my stay. The place was perfect for my needs as a solo traveller looking for a private getaway on a lake. Cozy but just the right size for a single traveller or a couple. Directions to the lakefront could have been a little clearer -- I went to the wrong dock initially! But that's more my fault than the host's. Loved hearing the loons at night and being able to chill on the front porch. I'd definitely stay here again! Thank you!"
Cozy One Bedroom studio suite in idyllic Adirondack setting

Lily Pad North at Loon Lake near Gore Mountain

9.8 out of 10, Exceptional, (25)
"Clean, open, and sunny. Happy to have the gas stove and washer/dryer. Bed was comfortable and bedding was most inviting. Couch a bit uncomfortable with the worn in dip where we sat. Very homey however felt exposed with the lack of window coverings. Loved the homey touches , flowers on the table, plush soft throws rolled in basket, plush bath towels ktexposethecoverings."
Lily Pad North at Loon Lake near Gore Mountain

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
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

Eagles Nest at Loon Lake near Gore Mountain

10.0 out of 10, Exceptional, (106)
"A fantastic location for those looking to get away in the Adirondacks. Conveniently close to Chestertown, as well as many outdoor activities, Eagles Nest was an awesome location to stay at with friends and family. "
Eagles Nest at Loon Lake near Gore Mountain

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

10.0 out of 10, Exceptional, (57)
"Incredible place and stay, highly recommended!"
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

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

9.2 out of 10, Wonderful, (35)
"Loved everything from the coffee maker to the views at this place. Fantastic!"
Lakefront cabin with beautiful loft, game room, views, private dock
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: Free WiFi, private patios, and fireplaces are included. 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.