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Chestertown Vacation Rentals

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Aug 5 - Aug 6
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Aug 6 - Aug 7
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Aug 8 - Aug 10
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Aug 15 - Aug 17

Vacation Rentals in Chestertown

Lake George Escape - Campground
Relax on the porch or by the grill in this serene cabin setting, surrounded by a beautifully maintained lawn and trees.

Lake George Escape - Campground

2.0 star property
8.4 out of 10, Very Good, (164)
"Nice place to staying "
Lake George Escape - Campground
Waterfront Home on Lake George w/ Boat Dock!
House (2 Bedrooms) | Interior

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!
Situated in a serene forest, this cabin features a stone chimney, small porch, and large windows.

Walk to Million Dollar Beach from this awesome Cottage!

10.0 out of 10, Exceptional, (159)
"Had a great time good location and plenty of room."
Walk to Million Dollar Beach from this awesome Cottage!
Terrace on the Lake – Private Lakefront with Breathtaking Views
Stunning two-story building with a central entrance and beautifully landscaped grounds.

Terrace on the Lake – Private Lakefront with Breathtaking Views

10.0 out of 10, Exceptional, (314)
"Everything was excellent and the house is amazing!"
Terrace on the Lake – Private Lakefront with Breathtaking Views
Bear Cub Barn, Bolton Landing
Enjoy cooking and dining in this well-equipped kitchen with a central island, sink, and ample counter space.

Bear Cub Barn, Bolton Landing

10.0 out of 10, Exceptional, (1)
"Exactly as we expected"
Bear Cub Barn, Bolton Landing
The Elms Waterfront Cottages
Cozy cabin-style room with a dining area, kitchenette, and sliding glass door to a patio with a picnic table.

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. "
$362 nightly
The price is $402
Aug 7 - Aug 8
Total includes taxes and fees
The Elms Waterfront Cottages
RUSTIC COUNTRY COTTAGE With SWIMMING POOL
Traditional home with a welcoming entrance, featuring a porch with white railing and lush green surroundings.

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
2 STORY ADIRONDACK LOG CABIN-SKI ! SKI! SKI!
Relax on the patio with a table and chairs, shaded by an umbrella, surrounded by trees and rocks.

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

8.8 out of 10, Excellent, (27)
"We thought the property was nicely decorated. Everything was functional and a good condition. At the time of the year we were going the pool was not an issue."
2 STORY ADIRONDACK LOG CABIN-SKI ! SKI! SKI!
RIVERFRONT ADIRONDACK LOG CABIN
Step up to the entrance of this cozy cabin, flanked by two chairs, and enjoy the serene atmosphere.

RIVERFRONT ADIRONDACK LOG CABIN

9.4 out of 10, Exceptional, (11)
"Very nice and roomy place with river views in Warrensburg! Worked great for our family!"
RIVERFRONT ADIRONDACK LOG CABIN
Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail
Relax in the cozy cabin with a seating area and access to the outdoor deck overlooking the water.

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

10.0 out of 10, Exceptional, (91)
"I stayed here with friends and it was perfect! The property and lake are amazing. Communication with Debby was extremely easy."
Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail
Lakefront Cabin & Campsite in the Adirondacks - Lake George/Saratoga vicinity.
Situated under a large tree, this bench offers a serene forest setting with a nearby body of water.

Lakefront Cabin & Campsite in the Adirondacks - Lake George/Saratoga vicinity.

10.0 out of 10, Exceptional, (6)
"Owners were super helpful and informative. Cabin was the perfect Inbetween for somone who loves camping and someone who doesn’t love camping. "
$197 nightly
The price is $212
Aug 13 - Aug 14
Total includes taxes and fees
Lakefront Cabin & Campsite in the Adirondacks - Lake George/Saratoga vicinity.
Lake George Water Front Cabin Spectacular Views
Relax on the deck with a serene lake view and distant mountains.

Lake George Water Front Cabin Spectacular Views

9.6 out of 10, Exceptional, (30)
"The house was perfect for my family! The teens loved kayaking! The view was absolutely stunning! Wish we could have stayed longer! Will stay again next year!"
$1,028 nightly
The price is $1,141
Sep 2 - Sep 3
Total includes taxes and fees
Lake George Water Front Cabin Spectacular Views
The Loon-ey Bin - Loon themed cottage less than 10 miles to Lake George
Enjoy a serene lakeside retreat with a sandy beach area, lush greenery, and a lifeguard tower for a safe and peaceful experience.

The Loon-ey Bin - Loon themed cottage less than 10 miles to Lake George

9.0 out of 10, Wonderful, (27)
"Quiet cabin/home in walking distance to the lake. If you are looking for a quiet getaway, this is the perfect cabin. Only 20 mins from downtown lake George. I plan on staying here again next year!! "
The Loon-ey Bin - Loon themed cottage less than 10 miles to Lake George
Adirondack Riverside Retreat - Minutes to Lake George, close to Gore Mountain
Relax in a hot tub under a shaded pergola.

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

9.8 out of 10, Exceptional, (187)
"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
Family Friendly - Pet Friendly
Guests can enjoy a peaceful stay in this two-story building surrounded by a well-maintained garden and a patio area with seating.

Family Friendly - Pet Friendly

9.8 out of 10, Exceptional, (62)
"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
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
Relax in a serene space with a circular bath, two large windows, and a cozy bench.

ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

10.0 out of 10, Exceptional, (87)
"This was a great little getaway. Would definitely come back. "
$246 nightly
The price is $273
Aug 6 - Aug 7
Total includes taxes and fees
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
Little Red Cabin by the Brook- 5m to Waterfall
Cozy attic retreat with a bed, TV, and hammock chair, perfect for relaxation.

Little Red Cabin by the Brook- 5m to Waterfall

9.4 out of 10, Exceptional, (17)
"Would definitely visit again!"
$238 nightly
The price is $264
Aug 7 - Aug 8
Total includes taxes and fees
Little Red Cabin by the Brook- 5m to Waterfall
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
Enjoy cooking in this well-lit kitchen with a central island, gas stove, and large window offering a view of the surrounding forest.

Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

10.0 out of 10, Exceptional, (321)
"Location was easy to get to. The house was beautifully decorated and located right on the water. Kitchen was fully stocked with pots, pans and utensils so it was easy to cook for the whole group! We had a great time staying here :) 10/10"
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
Breathtaking Mountain Views Surround New Lakefront Condo
Cozy living area with a stone fireplace, comfortable seating, and large windows.

Breathtaking Mountain Views Surround New Lakefront Condo

9.8 out of 10, Exceptional, (91)
"Beautiful location will definitely be booking it next year. The staff was amazing."
Breathtaking Mountain Views Surround New Lakefront Condo
Waterfall Gorge-ous Home w 200+ feet of river frontage -10 mi to Lake George
Sit on the wooden bench and enjoy the serene surroundings of this peaceful retreat.

Waterfall Gorge-ous Home w 200+ feet of river frontage -10 mi to Lake George

9.4 out of 10, Exceptional, (53)
"My 3 kids and I absolutely loved the spot. The stream in the back of the house was unique and gorgeous, Diane was communicative and pleasant. Highly recommended"
Waterfall Gorge-ous Home w 200+ feet of river frontage -10 mi to Lake George
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

Tiki Resort

Tiki Resort

10/10 Excellent
"Great staff "
Kelsi 1-night trip
Posted 19 hours ago
Tiki Resort

Frequently asked questions

Can I find vacation rentals in Chestertown?

Yes, we give you a choice of vacation rentals near well known points of interest in Chestertown, or you can choose a more remote option if you want a relaxing place to stay. Nature enthusiasts will enjoy the lakeside in Chestertown. Make sure you have time to check out the coffeehouses and forests during your trip.

What are some of the best vacation home rentals in Chestertown?

Family Friendly - Pet Friendly : This vacation home near Chestertown is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals will I find in Chestertown?

With 62 Expedia vacation rentals, you're sure 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 vacation rental in Chestertown like?

Vacation rentals are private properties you can book for a couple of days or more in Chestertown. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.