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Chestertown Vacation Rentals

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Check prices for these dates

In two weeks
Dec 12 - Dec 14
In two months
Jan 23 - Jan 25
In three months
Feb 20 - Feb 22
In four months
Mar 20 - Mar 22

Vacation Rentals in Chestertown

Exterior
Eagles Nest at Loon Lake near Gore Mountain

Vacation 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
Lake
Elizabeth. A Guest House Near Lake George.

Vacation Home in Chestertown

8.2 out of 10, Very Good, (45)
"The house was beautiful and charming and plenty of space. We have no complaints but recommend hand towels in the bathrooms. Probably will look up this place again for a skiing trip this winter."
United States
Dennis M Wilson J.
Elizabeth. A Guest House Near Lake George.
Fireplace
Lincoln Log Colony

Cabin in Lake George

2.0 star property
8.8 out of 10, Excellent, (10)
"The cabin was clean and ready when arrived. Corrina went above and beyond to make us feel welcome. We are ready to go back soon."
United States
Lynn
Lincoln Log Colony
House (2 Bedrooms) | Interior
Waterfront Home on Lake George w/ Boat Dock!

Cottage in Queensbury

3.0 star property
Waterfront Home on Lake George w/ Boat Dock!
Interior
Cozy, pet friendly, newly renovated chalet home with shared beach & water views

Vacation 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
Outdoor spa tub
ADK Riverside Retreat-Heated Pool-Hot Tub- close to Lake George and Gore

Vacation Home in Warrensburg

9.8 out of 10, Exceptional, (191)
"We had an unforgettable stay that truly elevated our entire vacation experience.The stay was absolutely fantastic, one of the best places we’ve ever stayedThis property has all the amenities required for a great vacation...its a flawless propertyIf anybody visiting Lake George, I would recommend this property 100%Thank you."
United States
nanda k.
ADK Riverside Retreat-Heated Pool-Hot Tub- close to Lake George and Gore
Interior
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

Cabin in North River

10.0 out of 10, Exceptional, (93)
"Great location beautiful view and very nice cabin thank you!"
United States
Aline B.
The price is ￥22,662
￥33,829 total
includes taxes & fees
Nov 30 - Dec 1
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
Outdoor spa tub
luxury log home mins from Lake George, w/ heated salt water pool!

Vacation Home in Warrensburg

10.0 out of 10, Exceptional, (169)
"Property was wonderful, so great to have a wonderful pool and hot tub. The playground was loved by our grandchildren. The house had everything anyone would need. Highly recommend."
United States
Alana K.
luxury log home mins from Lake George, w/ heated salt water pool!
Exterior
Walk to Million Dollar Beach from this awesome Cottage!

Cottage in Lake George

10.0 out of 10, Exceptional, (167)
"Property was very clean and was close to downtown and the beaches . Would stay here again"
United States
Lori S.
Walk to Million Dollar Beach from this awesome Cottage!
Exterior
Adirondack Bungalow Getaway

Vacation Home in Warrensburg

10.0 out of 10, Exceptional, (66)
"This property is quaint and comfy. It was easy to find and get to places we visited with ease. The neighborhood is quiet. The host Laney is responsive and very nice! We hope to return next year!"
United States
Kathy S.
The price is ￥15,321
￥30,353 total
includes taxes & fees
Nov 30 - Dec 1
Adirondack Bungalow Getaway
Exterior
Hickory Hill Mountaintop charming family friendly quiet very private lake view

Vacation Home in Bolton Landing

10.0 out of 10, Exceptional, (141)
"Very nice home, relaxing. "
United States
Stephen C.
Hickory Hill Mountaintop charming family friendly quiet very private lake view
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
Luxury Cabin, 1 Bedroom, Lake View | Living area | 42-inch Smart TV with digital channels, DVD player, streaming services
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 ￥23,367
￥29,841 total
includes taxes & fees
Nov 30 - Dec 1
Trout House Village Resort
Property grounds
Lake George Water Front Cabin Spectacular Views

Cabin in Ticonderoga

9.6 out of 10, Exceptional, (35)
"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!"
United States
Jillian B.
The price is ￥84,337
￥176,307 total
includes taxes & fees
Nov 30 - Dec 1
Lake George Water Front Cabin Spectacular Views
Outdoor dining
Family Friendly - Pet Friendly

Vacation 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
Terrace/patio
Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail

Vacation Home in Kattskill Bay

10.0 out of 10, Exceptional, (95)
"We had an awesome week of great weather. There was more than enough room for our family of 13 adults and 2 babies and every house was fully equipped in the kitchens. The lake is so clean and beautiful and the set up of the docks is perfect. The sunsets were amazing. Deb was so helpful and very quick to respond to us when we needed something. Would return next year."
United States
Janice F.
Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail
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
Exterior
Terrace on the Lake – Private Lakefront with Breathtaking Views

Vacation Home in Warrensburg

10.0 out of 10, Exceptional, (331)
"Has everything a large group or family needs, and is clean and well maintained"
United States
Bob M.
Terrace on the Lake – Private Lakefront with Breathtaking Views
Fridge, microwave, oven, stovetop
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

Vacation Home in Warrensburg

9.8 out of 10, Exceptional, (336)
"My family had an awesome stay. We’ve stayed at this property several times over the years and never disappoints. Owners are fantastic and very responsive. "
United States
Deb C.
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
Property grounds
Private Adirondack Getaway. Close to Lake George and VT for winter activities.

Vacation Home in Clemons

10.0 out of 10, Exceptional, (100)
"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.
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

Fort William Henry Hotel and Conference Center

Fort William Henry Hotel and Conference Center

10/10 Excellent
"Friendly staff, wonderful food, beautiful lake views, nice amenities. "
Kelly 2-night trip
Posted 1 day ago
Fort William Henry Hotel and Conference Center

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
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  • 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 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?

Terrace on the Lake – Private Lakefront with Breathtaking Views: This vacation home rental near Chestertown is located on a lake and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Chestertown?

With 58 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.