Photo by Julie Miller

Beach Hotels & Resorts in Chestertown from NZ$334

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Beach Hotels

Tonight
2 Oct - 3 Oct
Tomorrow
3 Oct - 4 Oct
This weekend
3 Oct - 5 Oct
Next weekend
10 Oct - 12 Oct

Best Chestertown Beach Hotels

Pine Tree Motel & Cabins
Exterior

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (141)
"Excellent location and staff was very friendly."
The price is NZ$334
includes taxes & fees
6 Oct - 7 Oct
Pine Tree Motel & Cabins
Friends Lake Inn
Premier Room

Friends Lake Inn

4.0 star property
8.8 out of 10, Excellent, (101)
"Staff was great. The inn is unique. Perfect!"
The price is NZ$448
includes taxes & fees
6 Oct - 7 Oct
Friends Lake Inn
The Fern Lodge
Lake view

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (47)
"Comfortable, friendly, beautiful lodge, spacious facilities"
The Fern Lodge
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
Sun-loungers

Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing

10.0 out of 10, Exceptional, (35)
"Beautifully appointed cabin in the woods. Love the hot tub, the kitchen and the entertainment areas - "
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
Cozy 3BR 3.5BA Lodge w/ Lake & Beach Access, Screened in Patio, Grill, Sunroom
Smart TV, books

Cozy 3BR 3.5BA Lodge w/ Lake & Beach Access, Screened in Patio, Grill, Sunroom

The price is NZ$792
includes taxes & fees
6 Oct - 7 Oct
Cozy 3BR 3.5BA Lodge w/ Lake & Beach Access, Screened in Patio, Grill, Sunroom
Eagles Nest at Loon Lake near Gore Mountain
Beach nearby

Eagles Nest at Loon Lake near Gore Mountain

10.0 out of 10, Exceptional, (112)
"This is the second time that our family has stayed at Eagle's Nest. We enjoyed our time together once again. We had plenty of room and the fire pit, game room and games, sand box and canoes/kayaks were a welcome addition once again. We love the area and this home accommodates our family nicely."
Eagles Nest at Loon Lake near Gore Mountain
Elizabeth. A Guest House Near Lake George.
Outdoor dining

Elizabeth. A Guest House Near Lake George.

8.2 out of 10, Very good, (45)
"Great place to celebrate with large family"
Elizabeth. A Guest House Near Lake George.
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (69)
"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
Peaceful Lakeside Retreat with Private Beach
Beach nearby, sun-loungers, beach towels

Peaceful Lakeside Retreat with Private Beach

9.4 out of 10, Exceptional, (23)
"The area was quiet and house was nice. Perfect for our needs."
Peaceful Lakeside Retreat with Private Beach
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
On the beach

#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

9.6 out of 10, Exceptional, (17)
"The views were absolutely amazing! We will definitely be back."
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
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.
View all properties

Top Chestertown Hotel Reviews

Lakefront Terrace Resort

Lakefront Terrace Resort

10/10 Excellent
"Great staff. Very accommodating "
jason 3-night trip
Posted 2 days ago
Lakefront Terrace Resort

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What is Chestertown like for travellers who love the beach?
Known for its lakeside setting, Chestertown offers a lot for the traveller planning a getaway.
What's the best accommodation option to stay near the beach in Chestertown?
The Fern Lodge is a top beach B&B with free breakfast and 8 hot tubs, and it's located close to Loon Lake Beach .
When's the best time for a beach holiday in Chestertown?
Plan your trip to the beach with a look at the seasons 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 is there to see and do around Chestertown?
After arriving and checking into your hotel, you'll probably want to explore your surroundings. If you're eager to check out the beaches, head to Rogers Memorial Park Beach or Veterans Memorial Park Beach for some relaxation by the water. Discover the area's lakeside setting, and make time for local attractions such as Loon Lake Beach and Friends Lake. Other things to see and do in the area are Loon Lake and Hudson River.
What's the best way to get to my beach hotel in Chestertown?
Here's some information to help you get to and around your beach accommodation in Chestertown more easily: Make your way to Chestertown with a flight to Glens Falls, NY (GFL-Floyd Bennett Memorial), the closest major airport which is located 23.6 mi (38 km) from the city centre. If you'd like to venture out around the area, you may want a rental car for your journey.