Title: Visit Chestertown: 2026 Travel Guide for Chestertown, New York | Expedia.com

[Hotels in Chestertown](https://expedia.com/Chestertown-Hotels.d89045.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.com/Chestertown-Vacation-Rentals.d89045.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.com/Cheap-Flights-To-Chestertown.d89045.Travel-Guide-Flights)[Car Rentals in Chestertown](https://expedia.com/Car-Rentals-In-Chestertown.d89045.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.com/Chestertown.d89045.Destination-Travel-Guides)

# Chestertown, NY

## Travel Guide

![Aerial view of Hudson River in upstate New York, Chestertown, Riparius Bridge. July 12, 2022](https://images.trvl-media.com/place/89045/d8935802-94c8-4419-b7bf-ae82c253406c.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Chestertown](https://images.trvl-media.com/place/89045/03fff121-2e0b-4e9d-87bf-e8549eff3948.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

## Visit Chestertown

Where to stay

Things to do

### Where to stay in Chestertown

![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Chester Shores

 When in Chester Shores, you can plan a visit to Loon Lake Beach and Loon Lake, some noteworthy sights in the nearby area. 

[](https://expedia.com/Lake-George-Chester-Shores.dx553248635976471458)

[See our Where To Stay guide](https://expedia.com/Chestertown.dx89045.Where-To-Stay?rfrr=TG.LP.Dest.Neighborhoods)

- Chestertown Hotel Deals
- Vacation Rentals in Chestertown

![Eagles Nest at Loon Lake near Gore Mountain](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956145/73dd065d_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Eagles Nest at Loon Lake near Gore Mountain

 Chestertown NY

Book a stay at this family-friendly vacation home in Chestertown. Enjoy a garden, laundry facilities, and a pool table. Popular attractions Loon Lake and Loon ...

[Get rates](https://expedia.com/Hotel-Search?startDate=4%2F14%2F2026&endDate=4%2F15%2F2026&selected=18956145&PinnedHotelID=18956145&HadPinnedHotel=true&regionId=89045)

[](https://expedia.com/Hotel-Search?startDate=4%2F14%2F2026&endDate=4%2F15%2F2026&selected=18956145&PinnedHotelID=18956145&HadPinnedHotel=true&regionId=89045)

![Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure.](https://images.trvl-media.com/lodging/121000000/120760000/120755100/120755074/be8d3406_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure.

 Chestertown NY

Stay at this vacation home in Chestertown. Enjoy free WiFi, tennis courts, and patios. Popular attractions Tripp Pond and Pack Demonstration Forest are located ...

10/10 Exceptional! (3 reviews)

This was our first vacation rental as we were reluctant to try it after reading horrible stores about hidden fees and a tons of house cleaning list. We took a plunge this time and I am glad we did it. If you cook a lot (not us), a large party (not us), then this is perfect. It was a bit too big for ...

Reviewed on Mar 25, 2026

[Get rates](https://expedia.com/Hotel-Search?startDate=4%2F14%2F2026&endDate=4%2F15%2F2026&selected=120755074&PinnedHotelID=120755074&HadPinnedHotel=true&regionId=89045)

[](https://expedia.com/Hotel-Search?startDate=4%2F14%2F2026&endDate=4%2F15%2F2026&selected=120755074&PinnedHotelID=120755074&HadPinnedHotel=true&regionId=89045)

![Six Flags Great Escape Lodge & Indoor Waterpark](https://images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/fcd6f5d2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Six Flags Great Escape Lodge & Indoor Waterpark

89 Six Flags Dr Queensbury NY

$169 nightly

$188 total

Apr 19 - Apr 20

Total with taxes and fees

Book a stay at this family-friendly resort in Queensbury. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the breakfast and the helpful staff ...

8/10 Very Good! (1,586 reviews)

The place is very nice, but it is very dated. We were able to check in early, which was very nice. Unfortunately, there were no clean towels in the waterpark area that were readily available - we had to wait half an hour for them. There were no buckets for the popcorn so instead I had to purchase ...

Reviewed on Mar 30, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F19%2F2026&endDate=4%2F20%2F2026&selected=1385446&PinnedHotelID=1385446&HadPinnedHotel=true&regionId=89045)

[See all 1,532 properties in Chestertown](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=4%2F1%2F2026&endDate=4%2F2%2F2026&regionId=89045)

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.

![Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure.](https://images.trvl-media.com/lodging/121000000/120760000/120755100/120755074/be8d3406_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure.

 Chestertown NY

Stay at this vacation home in Chestertown. Enjoy free WiFi, tennis courts, and patios. Popular attractions Tripp Pond and Pack Demonstration Forest are located ...

10/10 Exceptional! (3 reviews)

This was our first vacation rental as we were reluctant to try it after reading horrible stores about hidden fees and a tons of house cleaning list. We took a plunge this time and I am glad we did it. If you cook a lot (not us), a large party (not us), then this is perfect. It was a bit too big for ...

Reviewed on Mar 25, 2026

[](https://expedia.com/Chestertown-Hotels-Secluded-And-Cozy-Lakeside-Townhome-On-Tripp-Lake.h120755074.Hotel-Information)

![Eagles Nest at Loon Lake near Gore Mountain](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956145/73dd065d_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Eagles Nest at Loon Lake near Gore Mountain

 Chestertown NY

Book a stay at this family-friendly vacation home in Chestertown. Enjoy a garden, laundry facilities, and a pool table. Popular attractions Loon Lake and Loon ...

[](https://expedia.com/Chestertown-Hotels-Eagles-Nest-At-Loon-Lake-Near-Gore-Mountain.h18956145.Hotel-Information)

![Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George](https://images.trvl-media.com/lodging/77000000/76330000/76320400/76320395/c6d64672_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

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

 Chestertown NY

Stay at this apartment in Chestertown. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Friends Lake and Tripp Pond are located ...

10/10 Exceptional! (76 reviews)

Hosts on location are very friendly and go above and beyond to make the stay enjoyable . The girls love playing with the dogs pearl and ruby. Been coming for several years and plan to return.

Reviewed on Feb 18, 2026

[](https://expedia.com/Chestertown-Hotels-Unique-Adirondack-Estate-On-Hudson-River-Near-Gore-Mountain-Lake-George.h76320395.Hotel-Information)

[See all properties in Chestertown](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&regionId=89045&sort=VACATION_RENTAL)

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.

## Check Chestertown hotel availability

[Tonight

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=89045&startDate=2026-03-31&endDate=2026-04-01)[Mar 31 - Apr 1](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=89045&startDate=2026-03-31&endDate=2026-04-01)

[Tomorrow night

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=89045&startDate=2026-04-01&endDate=2026-03-02)[Apr 1 - Apr 2](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=89045&startDate=2026-04-01&endDate=2026-03-02)

[This weekend

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=89045&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026)[Apr 3 - Apr 5](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=89045&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026)

[Next weekend

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=89045&startDate=4%2F10%2F2026&endDate=4%2F12%2F2026)[Apr 10 - Apr 12](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=89045&startDate=4%2F10%2F2026&endDate=4%2F12%2F2026)

### Popular places to visit

![Loon Lake](https://images.trvl-media.com/place/553248635976196050/b1196dfe-0b1b-43de-9b4b-94dcffab0606.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Loon Lake

Commune with nature and explore the great outdoors at Loon Lake during your travels in Chestertown. While you're in the area, stroll along the lakeside. 

[](https://expedia.com/Loon-Lake-Lake-George.d553248635976196050.Vacation-Attraction)

#### Friends Lake

Commune with nature and explore the great outdoors at Friends Lake during your travels in Chestertown. While you're in the area, stroll along the lakeside. 

[](https://expedia.com/Friends-Lake-Lake-George.d553248635976195601.Vacation-Attraction)

#### Loon Lake Beach

If a restful vacation is part of your travel plans, Loon Lake Beach might be the perfect place to seek out during your trip to Chestertown. While you're in the area, stroll along the lakeside. 

[](https://expedia.com/Loon-Lake-Beach-Chestertown.d553248621554184980.Vacation-Attraction)

## Cities near Chestertown

![August 20 2024, Sunny afternoon summer aerial image of the area surrounding Bolton Landing, NY, USA and Lake George.](https://images.trvl-media.com/place/55597/c1cee649-2a4e-4ab8-8a25-4dfebb2ecf85.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Bolton Landing

![Creek and trees in New England in foliage season, panoramic view](https://images.trvl-media.com/place/139117/b981d45f-bb71-4ae4-8e49-4da9e4c0411c.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### North Creek

![GF0Y54 The Upper Hudson River in summer.  Warrensburg, NY.](https://images.trvl-media.com/place/171313/56336380-5c2b-4bfc-a7db-e9d033755265.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Warrensburg

![Dramatic Autumn Sunset over Lower Saranac Lake](https://images.trvl-media.com/place/183662/03a29937-6dee-4cf8-8c99-afc74a2252aa.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Diamond Point

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- [Adirondack Vacations ](https://www.expedia.com/Adirondack.d6349269.Destination-Travel-Guides)
- [Visit North Creek ](https://www.expedia.com/North-Creek.dx139117)
- [Visit Bolton Landing ](https://www.expedia.com/Bolton-Landing.dx55597)
- [Tannery Pond Community Center ](https://www.expedia.com/Tannery-Pond-Community-Center-North-Creek.d553248621532665407.Vacation-Attraction)
- [North Creek Vacations ](https://www.expedia.com/North-Creek.d139117.Destination-Travel-Guides)

- [Car rentals near Brant Lake ](https://www.expedia.com/Car-Rentals-In-Brant-Lake.d6347839.Car-Rental-Guide)
- [Car rentals near Pottersville ](https://www.expedia.com/Car-Rentals-In-Pottersville.d6349845.Car-Rental-Guide)
- [Car rentals near Wevertown ](https://www.expedia.com/Car-Rentals-In-Wevertown.d3000450116.Car-Rental-Guide)
- [Car rentals near Blue Line Outdoor Center ](https://www.expedia.com/Car-Rentals-In-Blue-Line-Outdoor-Center.d553248621532665412.Car-Rental-Guide)
- [Car rentals near Adirondack ](https://www.expedia.com/Car-Rentals-In-Adirondack.d6349269.Car-Rental-Guide)
- [Car rentals near Up Yonda Farm Environmental Education Center ](https://www.expedia.com/Car-Rentals-In-Up-Yonda-Farm-Environmental-Education-Center.d553248621532665355.Car-Rental-Guide)
- [Car rentals near North Creek ](https://www.expedia.com/Car-Rentals-In-North-Creek.d139117.Car-Rental-Guide)

- [Brant Lake Vacation Rentals ](https://www.expedia.com/Brant-Lake-Vacation-Rentals.d6347839.Travel-Guide-VacationRentals)
- [Pottersville Vacation Rentals ](https://www.expedia.com/Pottersville-Vacation-Rentals.d6349845.Travel-Guide-VacationRentals)
- [Adirondack Vacation Rentals ](https://www.expedia.com/Adirondack-Vacation-Rentals.d6349269.Travel-Guide-VacationRentals)
- [North Creek Vacation Rentals ](https://www.expedia.com/North-Creek-Vacation-Rentals.d139117.Travel-Guide-VacationRentals)

- Cities near Chestertown
- Places of interest

[Bolton Landing](https://expedia.com/Bolton-Landing.dx55597)[North Creek](https://expedia.com/North-Creek.dx139117)[Warrensburg](https://expedia.com/Warrensburg.dx171313)[Diamond Point](https://expedia.com/Diamond-Point.dx183662)[Brant Lake](https://expedia.com/Brant-Lake.dx6347839)[Johnsburg](https://expedia.com/Johnsburg.dx6349362)[Pottersville](https://expedia.com/Pottersville.dx6349845)[Wevertown](https://expedia.com/Wevertown.dx3000450116)[Riparius](https://expedia.com/Riparius.dx553248635975950120)

- [Loon Lake Beach ](https://expedia.com/Loon-Lake-Beach-Chestertown.d553248621554184980.Vacation-Attraction)
- [Six Flags Great Escape ](https://expedia.com/Six-Flags-Great-Escape-New-York.d6064469.Vacation-Attraction)
- [Gore Mountain Ski Resort ](https://expedia.com/Gore-Mountain-Ski-Resort-North-Creek.d6326108.Vacation-Attraction)
- [Lake George ](https://expedia.com/Lake-George-New-York.d642804417676009472.Vacation-Attraction)
- [Million Dollar Beach ](https://expedia.com/Million-Dollar-Beach-New-York.d6247910.Vacation-Attraction)
- [Lake George Steamboat Company ](https://expedia.com/Lake-George-Steamboat-Company-Lake-George.d6171515.Vacation-Attraction)
- [Fort William Henry Museum ](https://expedia.com/Fort-William-Henry-Museum-Lake-George.d6064463.Vacation-Attraction)
- [Hudson River ](https://expedia.com/Hudson-River-New-York.d681942362185793536.Vacation-Attraction)
- [Outlets at Lake George ](https://expedia.com/Outlets-At-Lake-George-Lake-George.d6210494.Vacation-Attraction)
- [The Sagamore Golf Club ](https://expedia.com/The-Sagamore-Golf-Club-Bolton-Landing.d828201277410185216.Vacation-Attraction)
- [Shepard's Beach Park ](https://expedia.com/Shepards-Beach-Park-Lake-George.d553248621554160470.Vacation-Attraction)
- [Lake George Dog Beach ](https://expedia.com/Lake-George-Dog-Beach-New-York.d6064457.Vacation-Attraction)
- [Adirondack Winery ](https://expedia.com/Adirondack-Winery-Lake-George.d6217555.Vacation-Attraction)
- [Lake George Shoreline Cruises ](https://expedia.com/Lake-George-Shoreline-Cruises-Lake-George.d6171519.Vacation-Attraction)
- [Adirondack Outlet Mall ](https://expedia.com/Adirondack-Outlet-Mall-Lake-George.d6173782.Vacation-Attraction)
- [Wild West Ranch and Western Town ](https://expedia.com/Wild-West-Ranch-And-Western-Town-Lake-George.d6171522.Vacation-Attraction)
- [Hearthstone Point Campground ](https://expedia.com/Hearthstone-Point-Campground-Lake-George.d553248621579082980.Vacation-Attraction)
- [House of Frankenstein Wax Museum ](https://expedia.com/House-Of-Frankenstein-Wax-Museum-Lake-George.d6064461.Vacation-Attraction)
- [Cool Insuring Arena ](https://expedia.com/Cool-Insuring-Arena-Glens-Falls.d6210487.Vacation-Attraction)
- [West Mountain Ski Resort ](https://expedia.com/West-Mountain-Ski-Resort-Queensbury.d6171711.Vacation-Attraction)
- [Natural Stone Bridge and Caves ](https://expedia.com/Natural-Stone-Bridge-And-Caves-Pottersville.d6230830.Vacation-Attraction)
- [Adirondack Extreme Adventure Course ](https://expedia.com/Adirondack-Extreme-Adventure-Course-Bolton-Landing.d553248621532665480.Vacation-Attraction)
- [SUNY Adirondack ](https://expedia.com/SUNY-Adirondack-Queensbury.d6210492.Vacation-Attraction)
- [Thirteenth Lake ](https://expedia.com/Thirteenth-Lake-North-River.d553248633939091612.Vacation-Attraction)

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