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Chestertown Holiday Rentals

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28 Sept - 29 Sept
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29 Sept - 30 Sept
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3 Oct - 5 Oct
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10 Oct - 12 Oct

Holiday 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
Trout House Village Resort
Living area

Trout House Village Resort

3.0 star property
9.6 out of 10, Exceptional, (15)
"Very friendly owner and beautiful views"
The price is HK$913
HK$1,208 total
includes taxes & fees
20 Oct - 21 Oct
Trout House Village Resort
Waterfront Home on Lake George w/ Boat Dock!
Interior

Waterfront Home on Lake George w/ Boat Dock!

3.0 star property
Waterfront Home on Lake George w/ Boat Dock!
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, (31)
"Comfy and enjoyable stay in Sabbath Day Point!"
New Lakeside Cottage 5 minutes from great hiking with large deck and lake view
Lake George Escape - Campground
2 bedrooms, WiFi

Lake George Escape - Campground

2.0 star property
8.4 out of 10, Very good, (168)
"Nice place to staying "
Lake George Escape - Campground
luxury log home mins from Lake George, w/ heated salt water pool!
Outdoor spa tub

luxury log home mins from Lake George, w/ heated salt water pool!

10.0 out of 10, Exceptional, (165)
"Very relaxing property and surrounding area"
luxury log home mins from Lake George, w/ heated salt water pool!
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
Interior

ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

10.0 out of 10, Exceptional, (91)
"So beautiful place "
The price is HK$1,478
HK$2,116 total
includes taxes & fees
7 Oct - 8 Oct
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
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
Vacation Cabin minutes from Lake George w/ Hot Tub
Fridge, microwave, oven, stovetop

Vacation Cabin minutes from Lake George w/ Hot Tub

10.0 out of 10, Exceptional, (13)
"The house is very clean and organized. "
The price is HK$1,400
HK$3,433 total
includes taxes & fees
29 Sept - 30 Sept
Vacation Cabin minutes from Lake George w/ Hot Tub
PET-FRIENDLY - Twilight Cabin a Unique Waterfront Log Cabin
Property grounds

PET-FRIENDLY - Twilight Cabin a Unique Waterfront Log Cabin

9.8 out of 10, Exceptional, (96)
"We enjoyed our stay so much that we'll be booking for next year. "
PET-FRIENDLY - Twilight Cabin a Unique Waterfront Log Cabin
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
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)
"The house was more beautiful than the pictures! So many spaces to gather. Pool was amazing - plenty of water toys. Hot tub was great and used often. Kids were in the pool even when it rained one day. We were out on the deck every day. The downstairs area was awesome. Small kitchen, game table, large living room with fireplace, extra bedrooms and a large bathroom with walk in shower. Everything we needed was supplied. Owners Charles and Yolanda were wonderful. Lake George was so close by. Will...
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, (140)
"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
Modern Lakeside Cabin - 2 Kayaks, 2 SUPS, perfect lake stay
Exterior

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

9.8 out of 10, Exceptional, (116)
"Beautiful location, wonderful little cottage. Communication tom was excellent overall, a very nice stay, highly recommend"
Modern Lakeside Cabin - 2 Kayaks, 2 SUPS, perfect lake stay
2 STORY ADIRONDACK LOG CABIN-SKI ! SKI! SKI!
Outdoor dining

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

8.8 out of 10, Excellent, (30)
"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!
Lake George Great Location with Lake Access
Property grounds

Lake George Great Location with Lake Access

10.0 out of 10, Exceptional, (22)
"We had a pleasant stay enjoyed the host and surroundings"
Lake George Great Location with Lake Access
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, (175)
"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
The Elms Waterfront Cottages
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 HK$2,042
HK$2,267 total
includes taxes & fees
29 Sept - 30 Sept
The Elms Waterfront Cottages
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
Fridge, microwave, oven, stovetop

Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

9.8 out of 10, Exceptional, (328)
"We made the most of our weekend even though the weather was "
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
SKI TIME! Adirondack Waterfront Log Cabin
Outdoor dining

SKI TIME! Adirondack Waterfront Log Cabin

9.0 out of 10, Wonderful, (83)
"This property was exactly what we wanted!"
SKI TIME! Adirondack Waterfront Log Cabin
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

Lakefront Terrace Resort

Lakefront Terrace Resort

10/10 Excellent
"Nice place we will come back"
kevin 1-night trip
Posted 4 days ago
Lakefront Terrace Resort

Find out more about Chestertown

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!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

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

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.