Book Holiday Homes in Chestertown

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Chestertown

Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

Warrensburg
Book a stay at this beach vacation home in Warrensburg. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Warren County Nature Trails and ...
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.

Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.

Clemons
Book a stay at this family-friendly vacation home in Clemons. Enjoy free WiFi, private pools, and a fitness center. Our guests praise the pool and the helpful ...
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.
Secluded Gore Mountain Pine-Panelled Getaway

Secluded Gore Mountain Pine-Panelled Getaway

Johnsburg
Book a stay at this family-friendly vacation home in Johnsburg. Enjoy free WiFi, a beach locale, and a water park. Popular attractions Gore Mountain Ski Resort ...
Secluded Gore Mountain Pine-Panelled Getaway
Save an average of 15% on thousands of hotels when you're signed in
Gorgeous Lakefront Home with a Fire Pit, Two Living Areas, and a Sunroom

Gorgeous Lakefront Home with a Fire Pit, Two Living Areas, and a Sunroom

Chestertown
Stay at this vacation home in Chestertown. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Friends Lake and Loon Lake Beach are located ...
Gorgeous Lakefront Home with a Fire Pit, Two Living Areas, and a Sunroom
Family Gem: Private Community Beach on Tripp Lake

Family Gem: Private Community Beach on Tripp Lake

2 out of 5
Chestertown
Stay at this vacation home in Chestertown. Enjoy a garden, tennis courts, and patios. Popular attractions Tripp Pond and Pack Demonstration Forest are located ...
Family Gem: Private Community Beach on Tripp Lake
luxury log home mins from Lake George, w/ heated salt water pool!

luxury log home mins from Lake George, w/ heated salt water pool!

Warrensburg
Book a stay at this family-friendly vacation home in Warrensburg. Enjoy free WiFi, private pools, and a water park. Our guests praise the helpful staff in our ...
luxury log home mins from Lake George, w/ heated salt water pool!
Adirondack Bungalow Getaway

Adirondack Bungalow Getaway

Warrensburg
The price is NZ$287 per night from 5 Jan to 6 Jan
NZ$287
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this vacation home in Warrensburg. Enjoy free WiFi, a water park, and a garden. Popular attractions Warren County Nature Trails and Hickory Ski Center ...
Adirondack Bungalow Getaway
Spacious lakefront chalet with washer/dryer, beach & dock

Spacious lakefront chalet with washer/dryer, beach & dock

Schroon Lake
Stay at this vacation home in Schroon Lake. Enjoy a water park, patios, and an in-room coffeemaker. Popular attractions Park Beach and Strand Theater are located ...
Spacious lakefront chalet with washer/dryer, beach & dock
4BR Home W/ Bar!

4BR Home W/ Bar!

Diamond Point
The price is NZ$1,263 per night from 2 Jan to 3 Jan
NZ$1,263
includes taxes & fees
2 Jan - 3 Jan 2025
Stay at this vacation home in Diamond Point. Enjoy air conditioning. Popular attractions Assembly Point and Hearthstone Point Campground are located nearby.
4BR Home W/ Bar!
Don't see what you're looking for?
See all available properties in Chestertown
View all properties
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.

Chestertown Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chestertown vacation homes are the perfect way for you to wing it.

Holiday houses in Chestertown let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chestertown in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chestertown adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chestertown with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chestertown vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chestertown Holiday Homes essential information

Accommodation
408 Holiday Homes
Lowest Price
NZ$201
Highest Price
NZ$1,263
Popular accommodation
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub! , Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT., Secluded Gore Mountain Pine-Panelled Getaway, Gorgeous Lakefront Home with a Fire Pit, Two Living Areas, and a Sunroom, Family Gem: Private Community Beach on Tripp Lake, luxury log home mins from Lake George, w/ heated salt water pool!, Adirondack Bungalow Getaway, Spacious lakefront chalet with washer/dryer, beach & dock, 4BR Home W/ Bar!

Top trending hotels in Chestertown

The Queensbury Hotel

The Queensbury Hotel

3 out of 5
88 Ridge St, Glens Falls, NY
Fully refundableReserve now, pay when you stay
The price is NZ$224 per night from 1 Jan to 2 Jan
NZ$224
includes taxes & fees
1 Jan - 2 Jan 2025
Stay at this 3-star business-friendly hotel in Glens Falls. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the bar in ...
The Queensbury Hotel
Six Flags Lodge & Indoor Waterpark

Six Flags Lodge & Indoor Waterpark

3.5 out of 5
89 Six Flags Dr, Queensbury, NY
The price is NZ$435 per night from 12 Jan to 13 Jan
NZ$435
includes taxes & fees
12 Jan - 13 Jan 2025
Stay at this 3.5-star family-friendly resort in Queensbury. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the breakfast and the helpful ...
Six Flags Lodge & Indoor Waterpark
Holiday Inn Resort Lake George - Adirondack Area, an IHG hotel

Holiday Inn Resort Lake George - Adirondack Area, an IHG hotel

3 out of 5
2223 Canada St, Lake George, NY
Fully refundable
The price is NZ$212 per night from 6 Jan to 7 Jan
NZ$212
includes taxes & fees
6 Jan - 7 Jan 2025
Stay at this 3-star family-friendly hotel in Lake George. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...
Holiday Inn Resort Lake George - Adirondack Area, an IHG hotel
Save an average of 15% on thousands of hotels when you're signed in
La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George

2 out of 5
1533 US-9, Lake George, NY
Fully refundableReserve now, pay when you stay
The price is NZ$201 per night from 12 Jan to 13 Jan
NZ$201
includes taxes & fees
12 Jan - 13 Jan 2025
Book a stay at this family-friendly hotel in Lake George. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
La Quinta Inn & Suites by Wyndham Lake George
Don't see what you're looking for?
See all available properties in Chestertown
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.