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Holiday Rentals in Chestertown

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Holiday Rentals in Chestertown

Eagles Nest at Loon Lake near Gore Mountain

10.0 out of 10, Exceptional, (111)
"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

3.0 star property
9.6 out of 10, Exceptional, (14)
"Very friendly owner and beautiful views"
The price is €131
includes taxes & fees
23 Oct - 24 Oct
Trout House Village Resort

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!

10.0 out of 10, Exceptional, (164)
"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

10.0 out of 10, Exceptional, (30)
"Comfy and enjoyable stay in Sabbath Day Point!"
New Lakeside Cottage 5 minutes from great hiking with large deck and lake view

Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.

10.0 out of 10, Exceptional, (96)
"Beautiful house and perfect for our group!"
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.

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

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

10.0 out of 10, Exceptional, (165)
"This property has everything you would need for a relaxing family vacation. There was something for all age groups. Baby items were available, bicycles, playset, pool toys and lets not forget the amazing game room in addition to the heated pool and hot tub. They have it all! "
luxury log home mins from Lake George, w/ heated salt water pool!

Vacation Cabin minutes from Lake George w/ Hot Tub

10.0 out of 10, Exceptional, (12)
"The house is very clean and organized. "
The price is €411
includes taxes & fees
28 Sept - 29 Sept
Vacation Cabin minutes from Lake George w/ Hot Tub

WATERFRONT and AFFORDABLE

8.0 out of 10, Very good, (31)
"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

9.8 out of 10, Exceptional, (191)
"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

Hickory Hill Mountaintop charming family friendly quiet very private lake view

10.0 out of 10, Exceptional, (139)
"Joyce was great to deal with. Very few issues arose but she was super responsive and accommodating whenever needed!"
Hickory Hill Mountaintop charming family friendly quiet very private lake view

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!

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

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

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

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 €247
includes taxes & fees
25 Sept - 26 Sept
The Elms Waterfront Cottages

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

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

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

Find out more about Chestertown

Find out more about Chestertown

Everything you need to know about Chestertown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chestertown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chestertown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chestertown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chestertown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chestertown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chestertown holiday rentals we have selected for you start as low as €131 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chestertown rentals

At Expedia, we put the best Chestertown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chestertown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chestertown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chestertown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 60 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.