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Chestertown Holiday Rentals

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Holiday Rentals in Chestertown

Our top choices for Chestertown holiday rentals

Eagles Nest at Loon Lake near Gore Mountain

10.0 out of 10, Exceptional, (111)
"A fantastic location for those looking to get away in the Adirondacks. Conveniently close to Chestertown, as well as many outdoor activities, Eagles Nest was an awesome location to stay at with friends and family. "
The price is AU$1,188
includes taxes & fees
7 Sept - 8 Sept
Eagles Nest at Loon Lake near Gore Mountain

Waterfront Home on Lake George w/ Boat Dock!

3.0 star property
Waterfront Home on Lake George w/ Boat Dock!

Walk to Million Dollar Beach from this awesome Cottage!

10.0 out of 10, Exceptional, (160)
"Jacki had the place as promised. Neat , clean and organized - tidy .. the charm of the cottage was wonderful !! The location was perfect !! Sleeping was fantastic. Heck we each had our own bathroom!! When we go back we’d definitely stay there again . Oh very quiet , peaceful. Two porches and great fireplace . Thank you Jacki "
Walk to Million Dollar Beach from this awesome Cottage!

Family Friendly - Pet Friendly

9.8 out of 10, Exceptional, (63)
"Had a great stay, check in was easy, the house was very clean and a great location to the downtown area and easy nice walking area! Would definitely stay here again!!"
Family Friendly - Pet Friendly

Bear Cub Barn, Bolton Landing

10.0 out of 10, Exceptional, (2)
"Fantastic stay with all the amenities of home. The house was well equipped and very comfortable. Quiet neighborhood with a large lawn. "
Bear Cub Barn, Bolton Landing

RUSTIC COUNTRY COTTAGE With SWIMMING POOL

8.0 out of 10, Very good, (20)
"Perfect for family to gather and perfect place with alot of option for outdoor activities 🤗"
RUSTIC COUNTRY COTTAGE With SWIMMING POOL

The Elms Waterfront Cottages

2.5 star property
8.4 out of 10, Very good, (16)
"We were treated like royalty here at the Elms. The owner, Chandler and his staff, go above and beyond. What a beautiful escape. We will most definitely return. "
The price is AU$530
includes taxes & fees
27 Aug - 28 Aug
The Elms Waterfront Cottages

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

10.0 out of 10, Exceptional, (91)
"Beautiful house! My family and I enjoyed our stay! House was fully stocked with everything you would need! The entire holiday weekend was cold and rainy but we still enjoyed ourselves! We used the hot tub a lot and the heated pool on the first day! The pool was cold on the other 3 days :( But overall we had a great time! "
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.

RIVERFRONT ADIRONDACK LOG CABIN

9.4 out of 10, Exceptional, (12)
"Very nice and roomy place with river views in Warrensburg! Worked great for our family!"
RIVERFRONT ADIRONDACK LOG CABIN

Housekeeping Cottage - near Lake George & Adirondacks

10.0 out of 10, Exceptional, (39)
"We had a wonderful time at the cottage!! Loved the outdoor firepit that you could cook over, fantastic option. We will definitely be back! 😄"
Housekeeping Cottage - near Lake George & Adirondacks

New Lakeside Cottage 5 minutes from great hiking with large deck and lake view

10.0 out of 10, Exceptional, (28)
"Everything was perfect. The house is gorgeous and had everything we needed. Love the location too!"
New Lakeside Cottage 5 minutes from great hiking with large deck and lake view

SKI TIME! Adirondack Waterfront Log Cabin

9.0 out of 10, Wonderful, (81)
"This property was exactly what we wanted!"
SKI TIME! Adirondack Waterfront Log Cabin

Trout House Village Resort

3.0 star property
9.8 out of 10, Exceptional, (12)
"Absolutely wonderful place and super friendly staff "
The price is AU$284
includes taxes & fees
2 Sept - 3 Sept
Trout House Village Resort

Adirondack Riverside Retreat - Minutes to Lake George, close to Gore Mountain

9.8 out of 10, Exceptional, (189)
"We had a wonderful weekend staying in warrensburg. We had plenty of space to enjoy each others company for a much needed winter retreat . "
Adirondack Riverside Retreat - Minutes to Lake George, close to Gore Mountain

Little Red Cabin by the Brook- 5m to Waterfall

9.4 out of 10, Exceptional, (17)
"Would definitely visit again!"
The price is AU$412
includes taxes & fees
1 Sept - 2 Sept
Little Red Cabin by the Brook- 5m to Waterfall

Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail

10.0 out of 10, Exceptional, (91)
"Reunion with old friends. Perfect for us all to have our own bedrooms. Many choices for hang spots, fun games and great huge deck. Owners and host are delightful to communicate with. We will plan to come back!"
Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail

Modern Lakeside Cabin - 2 Kayaks, 2 SUPS, perfect lake stay

9.8 out of 10, Exceptional, (114)
"Property was extremely clean and Tom was so helpful since I booked. Would definitely stay here again."
Modern Lakeside Cabin - 2 Kayaks, 2 SUPS, perfect lake stay

WATERFRONT and AFFORDABLE

8.0 out of 10, Very good, (29)
"Absolutely 10 stars. Private✔️Pet friendly✔️View ✔️ Remember, It's camping at its finest. Clean, comfortable and enough room for larger family's Highly recommend. Will be returning "
WATERFRONT and AFFORDABLE

2 STORY ADIRONDACK LOG CABIN-SKI ! SKI! SKI!

8.8 out of 10, Excellent, (28)
"Nice house, perfect location just outside of all the craziness. Not too far from it either. Easy access to everything. Would recommend staying again "
2 STORY ADIRONDACK LOG CABIN-SKI ! SKI! SKI!

Hickory Hill Mountaintop charming family friendly quiet very private lake view

10.0 out of 10, Exceptional, (139)
"Beautiful and spacious, clean and very accommodating. Twin beds were a bit narrow and a little uncomfortable, but definitely a great place to stay!!"
Hickory Hill Mountaintop charming family friendly quiet very private lake view
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

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$284 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?

Bear Cub Barn, Bolton Landing: This holiday home rental outside of Chestertown is located in a rural location, and offers a garden, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, an oven and a microwave.

How many holiday rentals will I find in Chestertown?

With 61 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.