Book Holiday Homes in Chestertown

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Featured Holiday Homes in Chestertown

Beautifully updated, Cozy 3 bedroom 2 bathroom house. WATER VIEWS!!

Beautifully updated, Cozy 3 bedroom 2 bathroom house. WATER VIEWS!!

Lake Luzerne
Stay at this vacation home in Lake Luzerne. Enjoy free WiFi, a garden, and patios. Popular attractions Wayside Beach and Sacandaga Outdoor Center are located ...
Beautifully updated, Cozy 3 bedroom 2 bathroom house. WATER VIEWS!!
A Quiet Private Home With All Your Needs Fulfilled. Fun Year-round Destination

A Quiet Private Home With All Your Needs Fulfilled. Fun Year-round Destination

Stoney Creek
Book a stay at this ski vacation home in Stony Creek. Enjoy free WiFi, a water park, and a fitness center.
A Quiet Private Home With All Your Needs Fulfilled. Fun Year-round Destination
Scenic lakefront retreat with water access, private dock, grill, W/D & fireplace

Scenic lakefront retreat with water access, private dock, grill, W/D & fireplace

Kattskill Bay
Stay at this vacation home in Queensbury. Enjoy a water park, a garden, and patios. Popular attractions Fort William Henry and Assembly Point are located ...
Scenic lakefront retreat with water access, private dock, grill, W/D & fireplace
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Hideaway Lodge - Glen Lake, Lake George

Hideaway Lodge - Glen Lake, Lake George

Lake George
Book a stay at this family-friendly vacation home in Lake George. Enjoy private pools, a garden, and patios. Popular attractions Six Flags Great Escape and Fort ...
Hideaway Lodge - Glen Lake, Lake George
Cozy Lake Luzerne Home - 1 Mi to Wayside Beach!

Cozy Lake Luzerne Home - 1 Mi to Wayside Beach!

Lake Luzerne
Stay at this vacation home in Lake Luzerne. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Wayside Beach and Sacandaga Outdoor ...
Cozy Lake Luzerne Home - 1 Mi to Wayside Beach!
PET-FRIENDLY - Adirondack Retreat w/ Private Sandy Beach Close To Season Events

PET-FRIENDLY - Adirondack Retreat w/ Private Sandy Beach Close To Season Events

North Creek
Book a stay at this beach vacation home in North Creek. Enjoy a beach locale, a water park, and a garden. Popular attractions Gore Mountain Ski Resort and Sagamore ...
PET-FRIENDLY - Adirondack Retreat w/ Private Sandy Beach Close To Season Events
Beautiful log home w/mountain views, gas fireplace & arcade games- close to lake

Beautiful log home w/mountain views, gas fireplace & arcade games- close to lake

Bolton Landing
Book a stay at this family-friendly vacation home in Bolton Landing. Enjoy a water park, a garden, and tennis courts. Popular attractions The Sembrich and Adirondack ...
Beautiful log home w/mountain views, gas fireplace & arcade games- close to lake
Family-Friendly Home w/ Hot Tub, Near Lake George!

Family-Friendly Home w/ Hot Tub, Near Lake George!

Warrensburg
Book a stay at this family-friendly vacation home in Warrensburg. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Warren County Nature ...
Family-Friendly Home w/ Hot Tub, Near Lake George!
The Sweet Home in Glens Falls

The Sweet Home in Glens Falls

Glens Falls
Stay at this vacation home in Glens Falls. Enjoy free WiFi, a garden, and patios. Popular attractions Six Flags Great Escape and Chapman Historical Museum are ...
The Sweet Home in Glens Falls
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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
514 Holiday Homes
Lowest Price
NZ$217
Highest Price
NZ$402
Popular accommodation
Beautifully updated, Cozy 3 bedroom 2 bathroom house. WATER VIEWS!!, A Quiet Private Home With All Your Needs Fulfilled. Fun Year-round Destination , Scenic lakefront retreat with water access, private dock, grill, W/D & fireplace, Hideaway Lodge - Glen Lake, Lake George, Cozy Lake Luzerne Home - 1 Mi to Wayside Beach!, PET-FRIENDLY - Adirondack Retreat w/ Private Sandy Beach Close To Season Events, Beautiful log home w/mountain views, gas fireplace & arcade games- close to lake, Family-Friendly Home w/ Hot Tub, Near Lake George!, The Sweet Home in Glens Falls

Top trending hotels in Chestertown

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

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

Chestertown
Stay at this apartment in Chestertown. Enjoy free WiFi, a garden, and patios. Popular attractions Friends Lake and Tripp Pond are located nearby.
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
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$217 per night from 6 Apr to 7 Apr
NZ$217
includes taxes & fees
6 Apr - 7 Apr
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 Great Escape Lodge & Indoor Waterpark

Six Flags Great Escape Lodge & Indoor Waterpark

3.5 out of 5
89 Six Flags Dr, Queensbury, NY
The price is NZ$402 per night from 10 Apr to 11 Apr
NZ$402
includes taxes & fees
10 Apr - 11 Apr
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 Great Escape Lodge & Indoor Waterpark
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Walk to Million Dollar Beach from this awesome Cottage!

Walk to Million Dollar Beach from this awesome Cottage!

Lake George
Stay at this cottage in Lake George. Enjoy free WiFi, a water park, and a garden. Popular attractions Fort William Henry and Six Flags Great Escape are located ...
Walk to Million Dollar Beach from this awesome Cottage!
Don't see what you're looking for?
See all available properties in Chestertown
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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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^Subject to availability and chosen travel dates.