Chestertown Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chestertown holiday rentals

Lily Pad South at Loon Lake near Gore Mountain

Lily Pad South at Loon Lake near Gore Mountain
Chestertown
9.8 out of 10, Exceptional, (48 reviews)
"We had a great time at the Lily Pad. Spent a day at Lake Placid and another day at Lake George...plus took in some of the sights and enjoyed the nearby beach and kayaksThe place was very nice...we would stay there again"
United States
Ray V.
The price is NZ$567
includes taxes & fees
17 Feb - 18 Feb
Lily Pad South at Loon Lake near Gore Mountain

Authentic Log Cabin with Lake Views and Sauna

Authentic Log Cabin with Lake Views and Sauna
Chestertown
The price is NZ$691
includes taxes & fees
12 Mar - 13 Mar
Authentic Log Cabin with Lake Views and Sauna

The Lily Pad at Loon Lake near Gore Mountain

The Lily Pad at Loon Lake near Gore Mountain
Chestertown
9.6 out of 10, Exceptional, (40 reviews)
"Comfortable stay with extended family. Would definitely stay again."
United States
Pam V.
The price is NZ$926
includes taxes & fees
11 Feb - 12 Feb
The Lily Pad at Loon Lake near Gore Mountain

Rustic Adirondack Retreat on Tripp Lake

Rustic Adirondack Retreat on Tripp Lake
Chestertown
10.0 out of 10, Exceptional, (46 reviews)
"We enjoyed our stay, the condo was very clean and beautifully decorated. The beds and couches were very comfortable and location was perfect with a local beach and lake and in driving distance to great restaurants and Lake George. Definitely recommend Linda’s property for your next vacation. "
United States
Natercia R.
The price is NZ$884
includes taxes & fees
18 Feb - 19 Feb
Rustic Adirondack Retreat on Tripp Lake

Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain
Chestertown
10.0 out of 10, Exceptional, (115 reviews)
"Cozy home in the Adirondacks. It had everything we needed for 19 relatives for a family reunion. "
United States
Kathy B.
The price is NZ$1,225
includes taxes & fees
8 Mar - 9 Mar
Eagles Nest at Loon Lake near Gore Mountain

Safari Tent nestled in the woods on the Schroon River with beach and island!

Safari Tent nestled in the woods on the Schroon River with beach and island!
North Hudson
4.0 out of 10, (4 reviews)
"well, we thought it was going to be glamping. It was worse than camping. It stunk it was dirty. The sheets were never changed. There was dirty dishes. The yard wasn’t mowed. It was just terrible. I would never do this again or recommend anyone to do it."
United States
Glynda
The price is NZ$373
includes taxes & fees
17 Feb - 18 Feb
Safari Tent nestled in the woods on the Schroon River with beach and island!

Trout House Village Resort

Trout House Village Resort
3.0 star property
Hague
9.8 out of 10, Exceptional, (22 reviews)
"Great updated cabin. "
United States
Diane
The price is NZ$434
includes taxes & fees
11 Feb - 12 Feb
Trout House Village Resort

Little Black Aframe by the Brook- 5m to Waterfall

Little Black Aframe by the Brook- 5m to Waterfall
Warrensburg
9.0 out of 10, Wonderful, (7 reviews)
"My wife and I had a great time. We would stay here again. Great communication with the host. Thanks!"
United States
Ted D.
The price is NZ$350
includes taxes & fees
11 Feb - 12 Feb
Little Black Aframe by the Brook- 5m to Waterfall

Beach - Family & Pet Friendly - Adirondack Cabin

Beach - Family & Pet Friendly - Adirondack Cabin
Indian Lake
The price is NZ$569
includes taxes & fees
11 Feb - 12 Feb
Beach - Family & Pet Friendly - Adirondack Cabin

Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!

Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
Fort Ann
10.0 out of 10, Exceptional, (24 reviews)
"Wonderful stay at a GREAT property!Couldn't ask for more!"
United States
Robert H.
The price is NZ$681
includes taxes & fees
16 Feb - 17 Feb
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!

ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT

ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT
North River
10.0 out of 10, Exceptional, (95 reviews)
"Cabin was very well done, clean- bed was super comfortable! The view of the mountains was fantastic- great for star watching too!"
United States
millie h.
The price is NZ$392
includes taxes & fees
11 Feb - 12 Feb
ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT

Rustic Vacation Rental for Couples near Hoffman Notch, New York

Rustic Vacation Rental for Couples near Hoffman Notch, New York
Schroon Lake
The price is NZ$278
includes taxes & fees
17 Feb - 18 Feb
Rustic Vacation Rental for Couples near Hoffman Notch, New York

Lakefront-Family & Pet Friendly-Adirondack Cabin

Lakefront-Family & Pet Friendly-Adirondack Cabin
Indian Lake
The price is NZ$582
includes taxes & fees
11 Feb - 12 Feb
Lakefront-Family & Pet Friendly-Adirondack Cabin

Handcrafted mountain cabin with gorgeous views

Handcrafted mountain cabin with gorgeous views
North River
9.8 out of 10, Exceptional, (49 reviews)
"This spot was ideal for us. Beauty, privacy, quiet, comfort. We used it as a base camp for exploring the Adirondacks. Felt remote but nearby North Creek had everything we needed. We had glorious weather and were outside most of the time, but the cabin was big enough for reading and playing games if we had needed to be inside more."
United States
Donna T.
The price is NZ$400
includes taxes & fees
11 Feb - 12 Feb
Handcrafted mountain cabin with gorgeous views

Little Red Cabin by the Brook- 5m to Waterfall

Little Red Cabin by the Brook- 5m to Waterfall
Warrensburg
9.4 out of 10, Exceptional, (19 reviews)
"Would definitely visit again!"
United States
Benjamin M.
The price is NZ$433
includes taxes & fees
22 Feb - 23 Feb
Little Red Cabin by the Brook- 5m to Waterfall

Cozy Adirondack Cabin Near Lake George w/ Wood Burning Stove & Lake Access

Cozy Adirondack Cabin Near Lake George w/ Wood Burning Stove & Lake Access
Hadley
10.0 out of 10, Exceptional, (21 reviews)
"Perfect remote location for a weekend away! Jackie is a great host and cabin was very clean and delicate. "
United States
Hanna D.
The price is NZ$373
includes taxes & fees
12 Feb - 13 Feb
Cozy Adirondack Cabin Near Lake George w/ Wood Burning Stove & Lake Access

Gorgeous Mountain Top Cabin with Beautiful Views

Gorgeous Mountain Top Cabin with Beautiful Views
North River
10.0 out of 10, Exceptional, (35 reviews)
"The cabin has everything you need in a small space, yet comfortable. The setting and views from it really cannot be beat!"
United States
Austin M.
The price is NZ$391
includes taxes & fees
11 Feb - 12 Feb
Gorgeous Mountain Top Cabin with Beautiful Views

Camp Lillian Gorgeous New Cabin with Mountain Views

Camp Lillian Gorgeous New Cabin with Mountain Views
North River
9.8 out of 10, Exceptional, (78 reviews)
"Just what we were looking for. Beautiful and peaceful. "
United States
Lisa S.
The price is NZ$391
includes taxes & fees
19 Feb - 20 Feb
Camp Lillian Gorgeous New Cabin with Mountain Views

Camp RiverWood on the Hudson River

Camp RiverWood on the Hudson River
North Creek
9.8 out of 10, Exceptional, (8 reviews)
"Beautiful cabin, clean, great location."
United States
Kyle D.
The price is NZ$416
includes taxes & fees
17 Feb - 18 Feb
Camp RiverWood on the Hudson River

The Pine Ridge Retreat - A Cozy Great Sacandaga Cottage with Private Lake Access

The Pine Ridge Retreat - A Cozy Great Sacandaga Cottage with Private Lake Access
Hadley
The price is NZ$384
includes taxes & fees
22 Feb - 23 Feb
The Pine Ridge Retreat - A Cozy Great Sacandaga Cottage with Private Lake Access
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chestertown Hotel Reviews

Find out more about Chestertown

Everything you need to know about Chestertown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chestertown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chestertown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chestertown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chestertown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chestertown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chestertown holiday rentals we have selected for you start as low as NZ$317 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chestertown rentals

At Expedia, we put the best Chestertown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chestertown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chestertown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chestertown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Chestertown?

Yes, there are holiday rentals close to the most popular sights in Chestertown, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the lakeside in Chestertown. Make sure you have time to check out the coffee shops and forests during your trip.

What are some of the best holiday rentals that Chestertown has to offer?

Elizabeth. A Guest House Near Lake George. : This highly rated holiday home rental in Chestertown is located on the waterfront, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. Our travellers also rate Eagles Nest at Loon Lake near Gore Mountain as a favourite home for rent in Chestertown.

How many holiday rentals will I find in Chestertown?

With 58 Expedia holiday rentals, you're guaranteed to find just the right place for your Chestertown stay.

What’s there to see and do in Chestertown?

Loon Lake Beach and Friends Lake are a couple of lovely local spots to get outside and enjoy nature. Loon Lake and Hudson River are other places to visit while you're in town.

What’s a holiday rental in Chestertown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chestertown. Holiday rentals provide amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family trips or small group gatherings.