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Chestertown Holiday Rentals

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Holiday Rentals in Chestertown

Exterior
Eagles Nest at Loon Lake near Gore Mountain

Holiday Home in Chestertown

10.0 out of 10, Exceptional, (113)
"This is the second time that our family has stayed at Eagle's Nest. We enjoyed our time together once again. We had plenty of room and the fire pit, game room and games, sand box and canoes/kayaks were a welcome addition once again. We love the area and this home accommodates our family nicely."
United States
Pam R.
Eagles Nest at Loon Lake near Gore Mountain
Fireplace
Lincoln Log Colony

Cabin in Lake George

2.0 star property
8.8 out of 10, Excellent, (10)
"Simple and easy. Perfect distance from down town LG. "
United States
Kenneth
Lincoln Log Colony
Interior
Waterfront Home on Lake George w/ Boat Dock!

Cottage in Queensbury

3.0 star property
Waterfront Home on Lake George w/ Boat Dock!
Outdoor spa tub
luxury log home mins from Lake George, w/ heated salt water pool!

Holiday Home in Warrensburg

10.0 out of 10, Exceptional, (169)
"This is a little gem of a house - great for big families - outstanding for kids - there is a playroom, playground, pool and hot tub. It was a wonderful place for our vacation "
United States
Dawn F.
luxury log home mins from Lake George, w/ heated salt water pool!
Exterior
Adirondack Bungalow Getaway

Holiday Home in Warrensburg

10.0 out of 10, Exceptional, (67)
"Great spot "
United States
Winter R.
The price is HK$764
HK$1,504 total
includes taxes & fees
9 Dec - 10 Dec
Adirondack Bungalow Getaway
Interior
Cozy, pet friendly, newly renovated chalet home with shared beach & water views

Holiday Home in Lake George

9.0 out of 10, Wonderful, (20)
"Wonderful house on the lake! Perfect location. Lovely beach. Really felt at home."
United States
Alison K.
Cozy, pet friendly, newly renovated chalet home with shared beach & water views
Exterior
Walk to Million Dollar Beach from this awesome Cottage!

Cottage in Lake George

10.0 out of 10, Exceptional, (167)
"The cottage was wonderful— cozy, impeccably clean, and well located. Loved our stay, and communication with the owner was seamless. "
United States
Donna M.
Walk to Million Dollar Beach from this awesome Cottage!
Exterior
COZY CUB CABIN Brookside • Lake George, Hot Tub, 24 acres w/ Brook

Cabin in Hague

10.0 out of 10, Exceptional, (42)
"Cozy cabin, close to great hikes."
United States
Melissa L.
COZY CUB CABIN Brookside • Lake George, Hot Tub, 24 acres w/ Brook
Living area
Trout House Village Resort

Cabin in Hague

3.0 star property
9.8 out of 10, Exceptional, (18)
"Very friendly owner and beautiful views"
United States
Anthony
The price is HK$1,165
HK$1,487 total
includes taxes & fees
9 Dec - 10 Dec
Trout House Village Resort
Property grounds
PET-FRIENDLY - Twilight Cabin a Unique Waterfront Log Cabin

Cabin in North Creek

9.8 out of 10, Exceptional, (102)
"What a beautiful place to stay. The cabin itself is cute and comfortable. The location is awesome."
United States
Dena M.
PET-FRIENDLY - Twilight Cabin a Unique Waterfront Log Cabin
Property grounds
Private Adirondack Getaway. Close to Lake George and VT for winter activities.

Holiday Home in Clemons

10.0 out of 10, Exceptional, (101)
"We had the best time! The hosts were responsive and they made our stay so enjoyable. We would definitely come again!"
United States
Leah B.
Private Adirondack Getaway. Close to Lake George and VT for winter activities.
Interior
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

Cabin in North River

10.0 out of 10, Exceptional, (93)
"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 HK$1,284
HK$1,875 total
includes taxes & fees
9 Dec - 10 Dec
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
Outdoor dining
Camp Lillian Gorgeous New Cabin with Mountain Views

Cabin in North River

9.8 out of 10, Exceptional, (77)
"Just what we were looking for. Beautiful and peaceful. "
United States
Lisa S.
The price is HK$1,284
HK$1,875 total
includes taxes & fees
9 Dec - 10 Dec
Camp Lillian Gorgeous New Cabin with Mountain Views
Outdoor dining
Family Friendly - Pet Friendly

Holiday Home in Lake George

9.8 out of 10, Exceptional, (68)
"Beautiful home in a great location"
United States
Savannah A.
Family Friendly - Pet Friendly
Fridge, microwave, oven, stovetop
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

Holiday Home in Warrensburg

9.8 out of 10, Exceptional, (336)
"We had a great week at this lovely home, something for everyone!The owners were very responsive to our needs!!I would definitely recommend this rental home!"
United States
Pamela L.
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
Exterior
Terrace on the Lake – Private Lakefront with Breathtaking Views

Holiday Home in Warrensburg

10.0 out of 10, Exceptional, (331)
"big and beautiful"
United States
anthony p.
Terrace on the Lake – Private Lakefront with Breathtaking Views
View from property
Lake George Waterfront Paradise Dock Slip

Holiday Home in Putnam Station

10.0 out of 10, Exceptional, (5)
"Beautiful house, amazing stay, great views! We enjoyed it!"
United States
Dawid R.
Lake George Waterfront Paradise Dock Slip
Outdoor dining
Handcrafted mountain cabin with gorgeous views

Cabin in North River

9.8 out of 10, Exceptional, (49)
"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 HK$1,323
HK$1,927 total
includes taxes & fees
9 Dec - 10 Dec
Handcrafted mountain cabin with gorgeous views
Terrace/patio
True Adirondack living. 3-bedroom house in tranquil Diamond Point.

Holiday Home in Diamond Point

10.0 out of 10, Exceptional, (7)
"Fantastic stay. Clean and welcoming. Plenty of staples supplied which is always helpful. Will visit again."
United States
Brad S.
The price is HK$2,335
HK$4,934 total
includes taxes & fees
5 Jan - 6 Jan 2026
True Adirondack living. 3-bedroom house in tranquil Diamond Point.
Property grounds
Bolton Bear House|Dock Slip|Hot Tub|12 Beds|Pet Friendly|

Holiday Home in Bolton Landing

2.0 star property
10.0 out of 10, Exceptional, (4)
"Our family had an incredible time at Bolton Bear house!!! Made our time in Lake George even better!!"
United States
lynn h.
Bolton Bear House|Dock Slip|Hot Tub|12 Beds|Pet Friendly|
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

Six Flags Great Escape Lodge & Indoor Waterpark

Six Flags Great Escape Lodge & Indoor Waterpark

10/10 Excellent
"Yes, will be coming back "
Marc 1-night trip
Posted 2 days ago
Six Flags Great Escape Lodge & Indoor Waterpark

Find out more about Chestertown

Search for holiday rentals in Chestertown on Expedia! You can easily find your home rentals, villas, holiday apartments in Chestertown using one of the methods below:

  • View our selection of featured holiday rentals in Chestertown
  • Use the map to find apartments and other holiday homes in the Chestertown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chestertown while they last

Look no further and take a look at our great range of rental properties in Chestertown!

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?

Terrace on the Lake – Private Lakefront with Breathtaking Views: This holiday home rental outside of 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 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.