Chestertown Holiday Rentals

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Our top choices for Chestertown holiday rentals

Authentic Log Cabin with Lake Views and Sauna

Authentic Log Cabin with Lake Views and Sauna
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Very nice cabin with amenities. Thank you for a great stay."
United States
Joe F.
The price is NZ$541
includes taxes & fees
6 Apr - 7 Apr
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, (41 reviews)
"Comfortable stay with extended family. Would definitely stay again."
United States
Pam V.
The price is NZ$753
includes taxes & fees
2 Apr - 3 Apr
The Lily Pad at Loon Lake near Gore Mountain

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$333
includes taxes & fees
23 Apr - 24 Apr
Trout House Village Resort

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, (98 reviews)
"Perfectly cozy, and just right for me and my tiny dog to get away for a few days!"
United States
Bobby R.
The price is NZ$352
includes taxes & fees
1 Apr - 2 Apr
ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT

Red Oak Cabin: Our cozy cabin is tucked away but still close to any adventure!

Red Oak Cabin: Our cozy cabin is tucked away but still close to any adventure!
Lake George
10.0 out of 10, Exceptional, (22 reviews)
"Stay was great!"
United States
Lieishea
The price is NZ$760
includes taxes & fees
31 Mar - 1 Apr
Red Oak Cabin: Our cozy cabin is tucked away but still close to any adventure!

RESTORED HISTORIC ADIRONDACK BIRD CAMP NEAR GORE MT WITH LOVELY MOUNTAIN VIEWS

RESTORED HISTORIC ADIRONDACK BIRD CAMP NEAR GORE MT WITH LOVELY MOUNTAIN VIEWS
North River
9.2 out of 10, Wonderful, (67 reviews)
"Had a great stay. Camp had rustic feel and was off the beaten path. Would stay again."
United States
Marcia M.
The price is NZ$392
includes taxes & fees
1 Apr - 2 Apr
RESTORED HISTORIC ADIRONDACK BIRD CAMP NEAR GORE MT WITH LOVELY MOUNTAIN VIEWS

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, (23 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$392
includes taxes & fees
2 Apr - 3 Apr
Cozy Adirondack Cabin Near Lake George w/ Wood Burning Stove & Lake Access

Camp Lillian Gorgeous New Cabin with Mountain Views

Camp Lillian Gorgeous New Cabin with Mountain Views
North River
9.8 out of 10, Exceptional, (81 reviews)
"Nice cozy cabin, close to the spa house."
United States
Anonymous traveller
The price is NZ$352
includes taxes & fees
1 Apr - 2 Apr
Camp Lillian Gorgeous New Cabin with Mountain Views

Handcrafted mountain cabin with gorgeous views

Handcrafted mountain cabin with gorgeous views
North River
9.8 out of 10, Exceptional, (50 reviews)
"Lovely little cabin tucked away near many hiking trails and the cute town of North Creek. Thanks so much!"
United States
Aileen T.
The price is NZ$348
includes taxes & fees
2 Apr - 3 Apr
Handcrafted mountain cabin with gorgeous views

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$348
includes taxes & fees
2 Apr - 3 Apr
Gorgeous Mountain Top Cabin with Beautiful Views

Beautiful cottage on quiet country road walking distance to charming North Creek

Beautiful cottage on quiet country road walking distance to charming North Creek
North Creek
9.8 out of 10, Exceptional, (51 reviews)
"It was exactly what I needed. Quiet and conveniently located for my plans. "
United States
Ruth A.
The price is NZ$373
includes taxes & fees
4 Apr - 5 Apr
Beautiful cottage on quiet country road walking distance to charming North Creek

Little Black Aframe by the Brook- 5m to Waterfall

Little Black Aframe by the Brook- 5m to Waterfall
Warrensburg
9.2 out of 10, Wonderful, (9 reviews)
"Cabin was super cozy and relaxing in a remote location. Perfect getaway "
United States
Blaine M.
The price is NZ$367
includes taxes & fees
1 Apr - 2 Apr
Little Black Aframe by the Brook- 5m to Waterfall

Camp RiverWood on the Hudson River

Camp RiverWood on the Hudson River
North Creek
9.8 out of 10, Exceptional, (11 reviews)
"Beautiful cabin, clean, great location."
United States
Kyle D.
The price is NZ$352
includes taxes & fees
5 Apr - 6 Apr
Camp RiverWood on the Hudson River

Beautiful cottage on scenic Adirondack hobby farm

Beautiful cottage on scenic Adirondack hobby farm
North River
9.6 out of 10, Exceptional, (63 reviews)
"This place was great! We enjoyed walking the property and hot tubbing. The farmhouse was unique, but amazing! Leslie and team were friendly, we enjoyed chats over breakfast and pizza. Would definitely visit again."
United States
Jake W.
The price is NZ$352
includes taxes & fees
5 Apr - 6 Apr
Beautiful cottage on scenic Adirondack hobby farm

Lakefront-Family & Pet Friendly-Adirondack Cabin

Lakefront-Family & Pet Friendly-Adirondack Cabin
Indian Lake
The price is NZ$768
includes taxes & fees
31 Mar - 1 Apr
Lakefront-Family & Pet Friendly-Adirondack Cabin

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$456
includes taxes & fees
31 Mar - 1 Apr
Little Red Cabin by the Brook- 5m to Waterfall

NEW! 10 Mi to Gore Mountain: Home in Adirondack Park

NEW! 10 Mi to Gore Mountain: Home in Adirondack Park
Olmstedville
10.0 out of 10, Exceptional, (8 reviews)
"Exactly what we needed & was stocked with great games, cooking supplies & blankets! Can’t wait to come back."
United States
Katlyn H.
The price is NZ$1,364
includes taxes & fees
1 Apr - 2 Apr
NEW! 10 Mi to Gore Mountain: Home in Adirondack Park

Serene 3-bedroom cabin in North Creek. Close to Gore Mountain ski resort.

Serene 3-bedroom cabin in North Creek. Close to Gore Mountain ski resort.
North Creek
The price is NZ$1,026
includes taxes & fees
2 Apr - 3 Apr
Serene 3-bedroom cabin in North Creek. Close to Gore Mountain ski resort.

Sweet New Cabin With Amazing Views Of The Hudson River

Sweet New Cabin With Amazing Views Of The Hudson River
North River
9.8 out of 10, Exceptional, (45 reviews)
"Fab cabin and loved the Japanese hot tub. Close to restaurants short drive and also close to gore mountain. We loved our stay!! "
United States
Ashling
The price is NZ$371
includes taxes & fees
1 Apr - 2 Apr
Sweet New Cabin With Amazing Views Of The Hudson River

Gore Mountain Lift View: Wade St. Apt 2

Gore Mountain Lift View: Wade St. Apt 2
North Creek
9.4 out of 10, Exceptional, (15 reviews)
"Thank you for an amazing stay. Everything was fantastic! "
United States
Tara F.
The price is NZ$451
includes taxes & fees
31 Mar - 1 Apr
Gore Mountain Lift View: Wade St. Apt 2
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 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$352 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?

Eagles Nest at Loon Lake near Gore Mountain: This highly rated holiday home rental in Chestertown is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 7 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.

How many holiday rentals will I find in Chestertown?

With 60 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.