Photo by Julie Miller

Hotels & Accommodation in Chestertown

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Check prices for these dates

Tonight
23 Feb - 24 Feb
Tomorrow
24 Feb - 25 Feb
This weekend
27 Feb - 01 Mar
Next weekend
06 Mar - 08 Mar

Where to stay in Chestertown?

1 bedroom, premium bedding, individually decorated
Friends Lake Inn
Friends Lake Inn
4.0 star property
Chestertown
8.6 out of 10, Excellent, (102 reviews)
The price is R3 577
R3 970 total
includes taxes & fees
25 Feb - 26 Feb
Friends Lake Inn
Lake view
The Fern Lodge
The Fern Lodge
3.5 star property
Chestertown
10.0 out of 10, Exceptional, (52 reviews)
Tucked into the forests of Chestertown, this cosy B&B offers a lakeside escape with a private beach. Enjoy complimentary breakfast, unwind in the sauna, or book a relaxing massage. Friends Lake and Loon Lake Beach are nearby for outdoor adventures.
The price is R7 939
R8 813 total
includes taxes & fees
25 Feb - 26 Feb
The Fern Lodge
Exterior
Llama House ADK
Llama House ADK
2.5 star property
Wevertown
9.2 out of 10, Wonderful, (34 reviews)
Experience the Adirondacks at this charming Wevertown lodge offering complimentary WiFi and parking. Just minutes from Gore Mountain Ski Resort, enjoy nearby hiking trails, kayaking, and mountain biking. A lobby fireplace welcomes you back after outdoor adventures.
The price is R2 333
R2 590 total
includes taxes & fees
25 Feb - 26 Feb
Llama House ADK
Exterior
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
3.0 star property
Bolton Landing
9.8 out of 10, Exceptional, (17 reviews)
The price is R17 226
R22 770 total
includes taxes & fees
25 Feb - 26 Feb
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
Premium bedding, down duvets, individually decorated
The Alpine Lodge
The Alpine Lodge
3.0 star property
North Creek
9.0 out of 10, Wonderful, (668 reviews)
The price is R2 423
R2 861 total
includes taxes & fees
23 Mar - 24 Mar
The Alpine Lodge
Restaurant
North Creek Lodge at Gore Mountain
North Creek Lodge at Gore Mountain
3.0 star property
North Creek
7.8 out of 10, Good, (434 reviews)
Warm mountain retreat near Gore Mountain Ski Resort offers free breakfast, WiFi, and parking. After hitting the slopes, unwind at the on-site restaurant or bar. Guests consistently praise the helpful staff and immaculate rooms, with High Pines Glades also nearby.
The price is R3 284
R3 645 total
includes taxes & fees
25 Feb - 26 Feb
North Creek Lodge at Gore Mountain
Front of property
Gore Mountain Lodge
Gore Mountain Lodge
2.0 star property
North Creek
9.2 out of 10, Wonderful, (213 reviews)
The price is R3 673
R4 077 total
includes taxes & fees
10 Mar - 11 Mar
Gore Mountain Lodge
Exterior
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
3.0 star property
Olmstedville
This cosy holiday home sits next to a golf course in Olmstedville, offering free WiFi and Smart TV entertainment. Explore nearby hiking trails, cross-country skiing routes, or visit Minerva Lake and Natural Stone Bridge and Caves.
The price is R4 078
R13 556 total
includes taxes & fees
25 Feb - 26 Feb
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
Exterior
Super 8 by Wyndham Lake George/Warrensburg Area
Super 8 by Wyndham Lake George/Warrensburg Area
2.5 star property
Lake George
8.8 out of 10, Excellent, (1 005 reviews)
Wake up to complimentary breakfast at this conveniently located motel near Warren County Nature Trails. Enjoy free WiFi and parking while exploring nearby Lake George and Six Flags Great Escape. Travellers praise the helpful staff and clean, quiet rooms despite busy seasons.
The price is R1 145
R1 271 total
includes taxes & fees
25 Feb - 26 Feb
Super 8 by Wyndham Lake George/Warrensburg Area
Exterior
Lodge at Schroon Lake
Lodge at Schroon Lake
3.0 star property
Schroon Lake
9.0 out of 10, Wonderful, (432 reviews)
Immersive Adirondack experience at this Schroon Lake gem offering a private beach, full-service marina, and restaurant with bar. After exploring nearby Strand Theatre, unwind in the sauna, hot tub, or 24-hour gym while enjoying free WiFi and parking.
The price is R2 326
R3 154 total
includes taxes & fees
05 Mar - 06 Mar
Lodge at Schroon Lake
Fridge, microwave, coffee/tea maker, electric kettle
Maple Leaf Motel
Maple Leaf Motel
2.5 star property
Schroon Lake
8.8 out of 10, Excellent, (561 reviews)
This charming Schroon Lake motel offers an 18-hole golf course and seasonal outdoor pool. Guests can enjoy snowmobiling, free WiFi, and complimentary parking. Located near Strand Theatre and Park Beach with clean rooms that previous guests praise.
The price is R1 909
R2 157 total
includes taxes & fees
25 Feb - 26 Feb
Maple Leaf Motel
Front of property
Silver Bay YMCA Inn and Conference Center
Silver Bay YMCA Inn and Conference Center
2.0 star property
Silver Bay
8.8 out of 10, Excellent, (139 reviews)
Escape to a peaceful retreat on Lake George with complimentary breakfast, WiFi, and parking. The 24-hour fitness centre keeps your routine intact while the restaurant satisfies your appetite. Located near Huletts Landing Marina, this quiet haven earns praise for its attentive staff.
The price is R1 661
R1 844 total
includes taxes & fees
02 Mar - 03 Mar
Silver Bay YMCA Inn and Conference Center
Indoor/outdoor pool
Lodges At Cresthaven
Lodges At Cresthaven
4.0 star property
Lake George
9.4 out of 10, Exceptional, (557 reviews)
Escape to this beach lodge on Lake George with easy access to local attractions including Dark Bay and Hearthstone Point Campground. After a workout in the 24-hour fitness centre, enjoy the restaurant or unwind at the bar. Free WiFi and parking enhance your stay.
The price is R2 469
R2 741 total
includes taxes & fees
25 Feb - 26 Feb
Lodges At Cresthaven
Flat-screen TV, DVD player
Sun Castle Resort
Sun Castle Resort
3.5 star property
Lake George
9.0 out of 10, Wonderful, (62 reviews)
The price is R3 830
R5 454 total
includes taxes & fees
25 Feb - 26 Feb
Sun Castle Resort
Garden
Pinebrook Motel
Pinebrook Motel
2.0 star property
Lake George
7.4 out of 10, Good, (188 reviews)
Positioned a short drive from Lake George and Six Flags Great Escape, this motel offers a seasonal outdoor pool for cooling off after exploring. Free WiFi and parking add value, while nearby Lakeside Trail invites nature enthusiasts.
The price is R913
R1 014 total
includes taxes & fees
08 Mar - 09 Mar
Pinebrook Motel
Private beach, kayaking, rowing
Sundowner on Lake George
Sundowner on Lake George
2.5 star property
Lake George
7.6 out of 10, Good, (246 reviews)
Escape to Lake George at this beachfront haven with a seasonal outdoor pool and soothing hot tub. Just a short drive from Six Flags Great Escape, enjoy the private beach and free parking while exploring nearby Black Mountain Loop.
The price is R1 301
R2 779 total
includes taxes & fees
02 Mar - 03 Mar
Sundowner on Lake George
Premium bedding, desk, laptop workspace, blackout curtains
Courtyard by Marriott Lake George
Courtyard by Marriott Lake George
3.0 star property
Lake George
9.2 out of 10, Wonderful, (1 004 reviews)
This lakeside hotel combines comfort with adventure, featuring a welcoming bar and 24-hour fitness centre. Just minutes from Six Flags Great Escape and Black Mountain Loop, enjoy free WiFi and parking after exploring nearby attractions.
The price is R1 796
R1 994 total
includes taxes & fees
26 Feb - 27 Feb
Courtyard by Marriott Lake George
Property entrance
Lake Haven Motel
Lake Haven Motel
2.5 star property
Lake George
7.4 out of 10, Good, (110 reviews)
Discover tranquil accommodation at Lake George with a refreshing seasonal outdoor pool and convenient free WiFi and parking. Located just a short drive from Six Flags Great Escape and Lakeside Trail, this motel offers easy access to popular attractions.
The price is R2 484
R4 093 total
includes taxes & fees
26 Mar - 27 Mar
Lake Haven Motel
Private beach, sun-loungers, kayaking
Surfside On The Lake
Surfside On The Lake
2.5 star property
Lake George
8.0 out of 10, Very good, (740 reviews)
Surfside On The Lake offers direct beach access and panoramic views from its rooftop terrace. Enjoy American cuisine at Club Hamilton, one of 2 restaurants, before exploring Lake George or driving to Six Flags Great Escape. Clean rooms and attentive staff enhance your stay.
The price is R3 436
R4 214 total
includes taxes & fees
01 Mar - 02 Mar
Surfside On The Lake
Bar (on property)
The Inn of Lake George
The Inn of Lake George
2.5 star property
Lake George
9.6 out of 10, Exceptional, (108 reviews)
This charming guesthouse offers complimentary WiFi and parking while placing you near Six Flags Great Escape. Guests consistently praise the helpful staff. Explore nearby Patriot of Lake George Museum or venture to Glens Falls, just 22 minutes away.
The price is R1 790
R1 987 total
includes taxes & fees
25 Feb - 26 Feb
The Inn of Lake George
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 neighbourhoods in Chestertown

Chester Shores

Chestertown's Chester Shores neighbourhood offers attractions, including Loon Lake.

Top landmarks in Chestertown

Loon Lake

Crystal waters of Loon Lake reflect the Adirondack Mountains, creating a paddler's paradise in upstate New York. Bring your own picnic and rent a kayak to spot the lake's namesake birds calling across the water.
See properties

Friends Lake

This private Adirondack lake offers pristine waters and tranquil surroundings for swimming, fishing, and kayaking. Access is limited to guests of lakeside accommodation, ensuring a peaceful retreat from crowds.
See properties

Learn more about Chestertown

Chestertown is well known for its attractions such as Loon Lake Beach and Friends Lake. The city has something for everyone including sights like Loon Lake and Hudson River within a secluded setting.

See all hotels in Chestertown
A winter scene
Photo by Julie Miller
Open Photo by Julie Miller

Check out reviews of Chestertown hotels guests love

Courtyard by Marriott Lake George

Courtyard by Marriott Lake George

10/10 Excellent
"Very happy with the hotel and room. "
Coleen 3-night trip
Posted 1 day ago
Courtyard by Marriott Lake George

Frequently asked questions

How much does a hotel room cost in Chestertown?
You can find top hotels in Chestertown from R1 014 with options to suit your budget and needs. To find an affordable hotel in Chestertown that meets all of your requirements, just apply filters on Hotels.com and sort hotels by "Price: low to high".
How much does a hotel room cost in Chestertown?
You can find top hotels in Chestertown from R1 014 with options to suit your budget and needs. To find an affordable hotel in Chestertown that meets all of your requirements, just apply filters on Hotels.com, and sort hotels by "Price: low to high". If you're a member, don't forget to sign in to your account to unlock more savings.
How can I find deals and earn rewards at Chestertown hotels?
Discover great deals on Chestertown hotel stays with Hotels.com. Take a look at hotel prices mid-week or during the low season as to find those off-peak deals. And make sure to check out our last-minute deals on Chestertown hotels.
How can I find deals and earn rewards at Chestertown hotels?
Members can save up to 20% on select hotels in Chestertown. Plus, Silver, Gold and Platinum members earn extra rewards on VIP Access bookings, making each stay even more rewarding.

Can I book Chestertown hotels with free cancellation?
To book a refundable Chestertown hotel on Hotels.com, just filter hotels by "Property cancellation options" and select "Fully refundable property". Many hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.
What are some of the best hotels in Chestertown for couples?
Choose a top-rated Chestertown romantic hotel and enjoy your couple's getaway. Our travellers love Friends Lake Inn, a hotel with a restaurant as well as champagne service. Another romantic hotel with top reviews is The Fern Lodge. This bed & breakfast offers a private hot tub and an in-room fireplace for a perfect stay. Discover more hotels in Chestertown on Hotels.com for couples by using the "Traveller experience" filter in your search and selecting "Adults only" or "Romantic".
What are some of the best Chestertown hotels with free parking?
If you're arriving by car, choosing a great Chestertown hotel with free parking is a plus. Our travellers' favourites include:
Can I book a refundable accommodation option in Chestertown?
If you want the flexibility to change your plans to Chestertown, most hotels offer refundable* rates that you can book. You can see this accommodation by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Chestertown if I want a holiday rental instead of a hotel?
If you want to find a good alternative to a hotel, review our selection of 59 holiday homes. You can also consider one of the 5 apartments or 19 cottages.
What will the weather in Chestertown be like during my visit?
The warmest months in Chestertown are usually July and August, with an average temperature of 18°C. January and February are the chilliest months, when the average temperature is -4°C. The rainiest months are June and July.
Why should I book my Chestertown hotel with Hotels.com?
There are plenty of reasons to book your Chestertown travel with us: our free cancellations on selected hotels* gives you the flexibility you're looking for, our Price Guarantee ensures that you always get the lowest price, and you can earn rewards on every booking.