Chestertown Holiday Rentals

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Our top choices for Chestertown holiday rentals

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 AU$968
includes taxes & fees
8 Mar - 9 Mar
Eagles Nest at Loon Lake near Gore Mountain
9.6 out of 10, Exceptional, (40 reviews)
"Comfortable stay with extended family. Would definitely stay again."
United States
Pam V.
The price is AU$660
includes taxes & fees
4 Mar - 5 Mar
The Lily Pad at Loon Lake near Gore Mountain
The price is AU$528
includes taxes & fees
3 Mar - 4 Mar
Authentic Log Cabin with Lake Views and Sauna
3.0 star property
9.8 out of 10, Exceptional, (22 reviews)
"Great updated cabin. "
United States
Diane
The price is AU$268
includes taxes & fees
31 Mar - 1 Apr
Trout House Village Resort
10.0 out of 10, Exceptional, (95 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 AU$284
includes taxes & fees
1 Apr - 2 Apr
ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT
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 AU$525
includes taxes & fees
3 Mar - 4 Mar
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
10.0 out of 10, Exceptional, (19 reviews)
"What a wonderful home away from home for the weekend! Cabin was exactly as described, extremely clean and welcoming. Host were very professional and kind. We definitely will be back"
United States
Taina R.
The price is AU$613
includes taxes & fees
3 Mar - 4 Mar
Red Oak Cabin: Our cozy cabin is tucked away but still close to any adventure!
9.8 out of 10, Exceptional, (79 reviews)
"Nice cozy cabin, close to the spa house."
United States
Anonymous traveller
The price is AU$284
includes taxes & fees
1 Apr - 2 Apr
Camp Lillian Gorgeous New Cabin with Mountain Views
9.2 out of 10, Wonderful, (66 reviews)
"See you next year amazing stay great food loved the bird camp cabin—- Brian, Darlene, Gracie and Hayden "
United States
Brian W.
The price is AU$320
includes taxes & fees
1 Apr - 2 Apr
RESTORED HISTORIC ADIRONDACK BIRD CAMP NEAR GORE MT WITH LOVELY MOUNTAIN VIEWS
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 AU$320
includes taxes & fees
4 Mar - 5 Mar
Cozy Adirondack Cabin Near Lake George w/ Wood Burning Stove & Lake Access
9.2 out of 10, Wonderful, (9 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 AU$299
includes taxes & fees
3 Mar - 4 Mar
Little Black Aframe by the Brook- 5m to Waterfall
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 AU$303
includes taxes & fees
1 Apr - 2 Apr
Beautiful cottage on quiet country road walking distance to charming North Creek
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 AU$284
includes taxes & fees
1 Apr - 2 Apr
Gorgeous Mountain Top Cabin with Beautiful Views
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 AU$284
includes taxes & fees
1 Apr - 2 Apr
Handcrafted mountain cabin with gorgeous views
9.8 out of 10, Exceptional, (8 reviews)
"Beautiful cabin, clean, great location."
United States
Kyle D.
The price is AU$358
includes taxes & fees
7 Mar - 8 Mar
Camp RiverWood on the Hudson River
10.0 out of 10, Exceptional, (13 reviews)
"This was our second time staying at Potash Road. Just like the first time, it was a wonderful experience. We will definitely be booking here again."
United States
Laurie S.
The price is AU$639
includes taxes & fees
3 Mar - 4 Mar
Vacation Cabin minutes from Lake George w/ Hot Tub
9.6 out of 10, Exceptional, (62 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 AU$314
includes taxes & fees
5 Mar - 6 Mar
Beautiful cottage on scenic Adirondack hobby farm
9.4 out of 10, Exceptional, (19 reviews)
"Would definitely visit again!"
United States
Benjamin M.
The price is AU$369
includes taxes & fees
3 Mar - 4 Mar
Little Red Cabin by the Brook- 5m to Waterfall
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 AU$1,109
includes taxes & fees
3 Mar - 4 Mar
NEW! 10 Mi to Gore Mountain: Home in Adirondack Park
The price is AU$496
includes taxes & fees
3 Mar - 4 Mar
Beach - Family & Pet Friendly - Adirondack Cabin
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 favourite 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 depend 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 AU$268 per night. Entering your travel dates in the search wizard might find you 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.