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Chestertown Vacation Rentals

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Check prices for these dates

In two weeks
Oct 31 - Nov 2
In one month
Nov 14 - Nov 16
In two months
Dec 12 - Dec 14
In three months
Jan 9 - Jan 11

Vacation Rentals in Chestertown

Eagles Nest at Loon Lake near Gore Mountain
Exterior
Eagles Nest at Loon Lake near Gore Mountain
10.0 out of 10, Exceptional, (112)
"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."
Eagles Nest at Loon Lake near Gore Mountain
Lincoln Log Colony
Fireplace
Lincoln Log Colony
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."
Lincoln Log Colony
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!
Trout House Village Resort
Luxury Cabin, 1 Bedroom, Lake View | Living area | 42-inch Smart TV with digital channels, DVD player, streaming services
Trout House Village Resort
3.0 star property
9.8 out of 10, Exceptional, (17)
"Beautiful views and wonderful staff. Provides an atmosphere for activities and relaxation while being able to access anywhere on the lake."
The price is ￥17,738
￥23,470 total
includes taxes & fees
Oct 20 - Oct 21
Trout House Village Resort
Terrace on the Lake – Private Lakefront with Breathtaking Views
Exterior
Terrace on the Lake – Private Lakefront with Breathtaking Views
10.0 out of 10, Exceptional, (323)
"this house is setup extremely well, especially for multiple couples. "
Terrace on the Lake – Private Lakefront with Breathtaking Views
Walk to Million Dollar Beach from this awesome Cottage!
Exterior
Walk to Million Dollar Beach from this awesome Cottage!
10.0 out of 10, Exceptional, (165)
"We had a great visit. The house was so clean and well equipped with everything needed. Having towels and bedding available was a huge benefit. Loved having two porches. "
Walk to Million Dollar Beach from this awesome Cottage!
New Lakeside Cottage 5 minutes from great hiking with large deck and lake view
Exterior
New Lakeside Cottage 5 minutes from great hiking with large deck and lake view
10.0 out of 10, Exceptional, (32)
"Comfy and enjoyable stay in Sabbath Day Point!"
New Lakeside Cottage 5 minutes from great hiking with large deck and lake view
Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail
Terrace/patio
Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail
10.0 out of 10, Exceptional, (94)
"Great experience. Richard and his property manager were fantastic. Highly recommend this lakefront property."
Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail
Lake George Water Front Cabin Spectacular Views
Property grounds
Lake George Water Front Cabin Spectacular Views
9.6 out of 10, Exceptional, (34)
"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!"
The price is ￥74,839
￥161,947 total
includes taxes & fees
Oct 15 - Oct 16
Lake George Water Front Cabin Spectacular Views
Cozy Family Friendly Lake View Home w / Easy Trip to Town & Beach
Smart TV, DVD player
Cozy Family Friendly Lake View Home w / Easy Trip to Town & Beach
9.6 out of 10, Exceptional, (177)
"Family vacation . 6 adults 2 kids. Absolutely gorgeous location. You have beautiful mountain all to yourself . Then can walk to the town in a few minutes with great restaurants . So total privacy but then short walk to town. Beds comfortable. If I could give more than 5 stars I would. "
Cozy Family Friendly Lake View Home w / Easy Trip to Town & Beach
Family Friendly - Pet Friendly
Outdoor dining
Family Friendly - Pet Friendly
9.8 out of 10, Exceptional, (66)
"Absolutely loved this spot. Easy walk down to the beach and convenient to town. Check in process went flawless and the place was in great condition. We did have to reach out to the property team while we were there and they were super responsive. "
Family Friendly - Pet Friendly
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.
Property grounds
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.
10.0 out of 10, Exceptional, (99)
"Beautiful house and perfect for our group!"
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.
WATERFRONT and AFFORDABLE
Exterior
WATERFRONT and AFFORDABLE
8.0 out of 10, Very Good, (32)
"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
Little Black Aframe by the Brook- 5m to Waterfall
Terrace/patio
Little Black Aframe by the Brook- 5m to Waterfall
8.8 out of 10, Excellent, (5)
"My wife and I had a great time. We would stay here again. Great communication with the host. Thanks!"
The price is ￥15,716
￥32,382 total
includes taxes & fees
Oct 15 - Oct 16
Little Black Aframe by the Brook- 5m to Waterfall
Adirondack Riverside Retreat - Minutes to Lake George, close to Gore Mountain
Outdoor spa tub
Adirondack Riverside Retreat - Minutes to Lake George, close to Gore Mountain
9.8 out of 10, Exceptional, (191)
"Amazing property, clean and roomy"
Adirondack Riverside Retreat - Minutes to Lake George, close to Gore Mountain
Hickory Hill Mountaintop charming family friendly quiet very private lake view
Exterior
Hickory Hill Mountaintop charming family friendly quiet very private lake view
10.0 out of 10, Exceptional, (141)
"This property is great for a group outing. Spacious house with plenty of room for our group. The property is fairly secluded with a private driveway but Bolton landing is just a 5 minute drive down the hill. Large deck perfect for group dinner and a beautiful view of lake George. "
Hickory Hill Mountaintop charming family friendly quiet very private lake view
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
Fridge, microwave, oven, stovetop
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
10.0 out of 10, Exceptional, (331)
"We all had a wonderful time. Would return again"
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
Camp Lillian Gorgeous New Cabin with Mountain Views
Outdoor dining
Camp Lillian Gorgeous New Cabin with Mountain Views
9.8 out of 10, Exceptional, (74)
"The Lillian cabin was great!! It was not only beautifully made but it had everything we needed including a peaceful and quiet two nights in the Adirondacks!!"
The price is ￥24,190
￥35,578 total
includes taxes & fees
Nov 2 - Nov 3
Camp Lillian Gorgeous New Cabin with Mountain Views
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
Interior
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
10.0 out of 10, Exceptional, (92)
"Great location beautiful view and very nice cabin thank you!"
The price is ￥28,726
￥41,116 total
includes taxes & fees
Oct 21 - Oct 22
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
The Elms Waterfront Cottages
Condo | In-room dining
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 ￥39,687
￥44,053 total
includes taxes & fees
Oct 15 - Oct 16
The Elms Waterfront Cottages
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

Country Inn & Suites by Radisson, Lake George (Queensbury), NY

Country Inn & Suites by Radisson, Lake George (Queensbury), NY

10/10 Excellent
"Great"
James 2-night trip
Posted 16 hours ago
Country Inn & Suites by Radisson, Lake George (Queensbury), NY

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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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?

Eagles Nest at Loon Lake near Gore Mountain: This highly rated vacation home rental in 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 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a pool table.

How many vacation rentals will I find in Chestertown?

With 60 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.