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Featured Apartments in Chestertown and around

Contemporary king w/futon

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

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

10.0 out of 10, Exceptional, (55)
"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!

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

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

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 €249
includes taxes & fees
9 Sept - 10 Sept
Gore Mountain Lift View: North Creek Main St Apt 2

Bolton Landing Suite w/ Deck, Lake George Access

10.0 out of 10, Exceptional, (11)
"The property owners were very communicative and the information at the house is excellent about things to do."
Bolton Landing Suite w/ Deck, Lake George Access

Lake George Getaway with SAUNA!

10.0 out of 10, Exceptional, (7)
"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!

Charming 2-bedroom apartment in delightful Lake George Village

10.0 out of 10, Exceptional, (1)
"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

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

10.0 out of 10, Exceptional, (66)
"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!

Cozy Lakeside Apartment - 5 Min Walk to Downtown!

9.8 out of 10, Exceptional, (7)
"It was a Great location"
The price is €346
includes taxes & fees
2 Sept - 3 Sept
Cozy Lakeside Apartment - 5 Min Walk to Downtown!

Modern Apt Near Lake George - Walk to Beach!

9.6 out of 10, Exceptional, (16)
"Great location and nice stay"
Modern Apt Near Lake George - Walk to Beach!

Vintage Market-Charming 2-bedroom with AC, WiFi in fantastic Lake George

10.0 out of 10, Exceptional, (1)
"Hands down, best place to stay in Lake George! The cabin was amazing and the staff friendly. I would recommend to anyone looking to stay in the Lake George area."
Vintage Market-Charming 2-bedroom with AC, WiFi in fantastic Lake George

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 "
Lily Pad North at Loon Lake near Gore Mountain

Lake George Great Location with Lake Access

10.0 out of 10, Exceptional, (21)
"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 €391
includes taxes & fees
24 Sept - 25 Sept
Charming Ground floor 2-bedroom apartment with WiFi, AC in tranquil Glens Falls

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

Unique Loft Downtown Glens Falls

8.0 out of 10, Very good, (1)
"This loft apartment was super cute and the layout was well-thought out. The exposed brick walls and decor made the space comfortable as a hang out and was in a great location - right downtown and walkable to amazing restaurants. The host was not as responsive as I'm used to but did provide check-in instructions when asked and allowed a late check-out. While there is designated parking in the back of the building, it's shared with a shop so wasn't available at check-in. Luckily, the building was...
Unique Loft Downtown Glens Falls

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 €233
includes taxes & fees
9 Sept - 10 Sept
Gore Mountain Lift View, The Eagles Nest: 251 Main St, Fl 3

Lakefront Bolton Retreat w/ Balcony + Views!

10.0 out of 10, Exceptional, (20)
"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!
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

Find out more about Chestertown

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
341
Accommodation
82 Apartments
Lowest Price
€233
Highest Price
€391

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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 apartments instead of traditional hotels?
Often more spacious than a traditional hotel room, an apartment includes a kitchen, so you can have some home-cooked meals. Apartments are ideal for families who want the conveniences of home but also for solo travellers who want to stay in at night and plan out their next day.
What's the best apartment for a stay in Chestertown?
Listed below are some of the favourite apartments in the area: Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George: Includes free WiFi, a patio and a fireplace . Access to on-site 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 a patio are included . Access to on-site laundry facilities is available on site .
How many apartments will I find in Chestertown?
Expedia has 7 apartments to book in Chestertown.
What will the weather be like in Chestertown?
Although 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 temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chestertown are January, March, November and December, with each month seeing an average of 33 cm 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 heart of the city. If you'd like to venture out around the area, you may want to rent a car for your trip.