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Holiday Rentals in Chestertown

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Holiday Rentals in Chestertown

Fridge, microwave, oven, stovetop
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
10.0 out of 10, Exceptional, (38)
"The place was amazing!!! So clean and had everything you need to stay away from home!!! Our do Oliver especially loved playing with Ruby and Pearl!!!"
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Exterior
Private child-friendly home with game room, high-speed WiFi, and wraparound deck
9.8 out of 10, Exceptional, (48)
"Clean property. Kids enjoyed games in basement."
Private child-friendly home with game room, high-speed WiFi, and wraparound deck
Outdoor dining
Cozy retreat with fireplace, kayaks, and shared beach/pond access
8.8 out of 10, Excellent, (9)
"We loved the days we stayed there, beautiful environment, very nice view. Be careful with the mosquitos, they came out in the evening."
Cozy retreat with fireplace, kayaks, and shared beach/pond access
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Property grounds
Peaceful Lakeside Retreat with Private Beach
9.4 out of 10, Exceptional, (9)
"We stay in Lake George every year for Labor Day. Although we love it, I wanted something more peaceful. This place was amazing. Very clean, quiet and lits to do right there on the property. We ate at George Henry's, the food was fantastic. Its only about a 20 min drive to Lake George, so we got the best of both worlds 😊 Would love to come back again next year!"
Peaceful Lakeside Retreat with Private Beach
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
10.0 out of 10, Exceptional, (63)
"Beautiful mountain views"
The price is €200
includes taxes & fees
23 May - 24 May
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
Fridge, microwave, oven, stovetop
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
9.8 out of 10, Exceptional, (278)
"Stayed for our friends bachelorette. It was a beautiful home. Master bedroom bed was very load and uncomfortable but other rooms were comfy. The view was amazing. Overall would definitely stay again."
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!
Property grounds
Cottage - near Lake George & Adirondacks - year round
10.0 out of 10, Exceptional, (27)
"Much of the typical Lake George activities were closed since we visited during April, but we were very happy to stay here and will definitely return! It was the perfect space for us two (with extra to fit an additional friend or 2). Owner provided towels, pans, grill, coffee, etc for the stay which is greatly appreciated. It was close distance to anywhere we needed to go for groceries, activities, stores! Sad to go but I look forward to future travels here :)"
Cottage - near Lake George & Adirondacks - year round
Property grounds
Secluded retreat. Great for families. Walk to Trout lake. High Speed Internet.
10.0 out of 10, Exceptional, (49)
"Group of 4 adult friends spent 2 nights around the eclipse. It was perfect! Clear communication before and during. Comfy beds, large living areas to hang out, we utilized the ample facilities (3 full bathrooms, fireplace, etc.). Would stay again"
The price is €657
includes taxes & fees
23 May - 24 May
Secluded retreat. Great for families. Walk to Trout lake. High Speed Internet.
Fridge, microwave, oven, stovetop
Cozy, pet friendly cabin minutes to lake George village
9.8 out of 10, Exceptional, (12)
"Clean, well furnished, nice neighborhood. Great community. Bed was too soft for my wife but everything else was perfect!"
Cozy, pet friendly cabin minutes to lake George village
Outdoor dining
2 STORY ADIRONDACK LOG CABIN-SKI ! SKI! SKI!
8.6 out of 10, Excellent, (15)
"Great Cabin!! Close to ALL."
2 STORY ADIRONDACK LOG CABIN-SKI ! SKI! SKI!
Exterior
Modern Lakeside Cabin - 2 Kayaks, 2 SUPS, perfect lake stay
9.8 out of 10, Exceptional, (94)
"We had a lovely stay. The cottage is charming and perfectly appointed. It is comfortable and full of amenities. We wanted a place that was located in a beautiful setting so that we can relax, but close enough to enjoy the attractions of Lake George and beyond and this location fit the bill. Tom was very gracious and responsive. He made sure everything was perfect for our trip. Would love to come back!"
Modern Lakeside Cabin - 2 Kayaks, 2 SUPS, perfect lake stay
Fridge, microwave, oven, stovetop
Charming cabin with three river-view decks & private setting
9.8 out of 10, Exceptional, (6)
"Great location to Gore Mountain, which was our main reason for our trip! Comfortable and lots of space. Beautiful surroundings! Thank you!!"
The price is €344
includes taxes & fees
23 May - 24 May
Charming cabin with three river-view decks & private setting
Beach
Adirondack Creekside Cottage-Sportmen’s Delight
10.0 out of 10, Exceptional, (36)
"Great time awesome fishing cottage was super clean and maintained"
Adirondack Creekside Cottage-Sportmen’s Delight
Property grounds
SKI TIME! Adirondack Waterfront Log Cabin
9.2 out of 10, Wonderful, (68)
"This was a 5-day, large family, vacation. There were a few minor issues, but nothing we couldn't overcome. We absolutely loved the location. There were a couple of days that we didn't even leave the property. The mosquitos were horribly, horribly bad! We went through a lot of insect spray and tiki torch fuel, but we were prepared for them. Thanks, Lisa"
SKI TIME! Adirondack Waterfront Log Cabin
Fridge, microwave, oven, stovetop
Lake George Great Location with Lake Access
10.0 out of 10, Exceptional, (9)
"One bedroom apartment with additional futon in bedroom. Perfectly stocked kitchen, upgrade linens, great location on quieter side of lake with private parking, outdoor space and great views. Less than 100' walk to lake edge. Very nice, accommodating owner/manager. We were there for 5 days to celebrate a Birthday and take advantage of boating on the lake and the wonderful variety of restaurants locally. We'll be back!"
Lake George Great Location with Lake Access
Exterior
Hickory Hill Mountaintop charming family friendly quiet very private lake view
10.0 out of 10, Exceptional, (120)
"This home is so beautiful and it was the right place for our family getaway. Very clean and you feel at home as soon as you walked in the door. Kitchen was large and stocked with everything you would need and more. Lots of games and the pool table,ping pong table and foosball, was Soo fun. The owner Joyce was very good at communicating when we had any questions. We made some wonderful family memories. Would definitely stay again."
Hickory Hill Mountaintop charming family friendly quiet very private lake view
Exterior
Handcrafted mountain cabin with gorgeous views
9.8 out of 10, Exceptional, (29)
"Perfect cozy getaway. Peaceful!"
The price is €198
includes taxes & fees
30 May - 31 May
Handcrafted mountain cabin with gorgeous views
Exterior
Adirondack Bungalow Getaway
10.0 out of 10, Exceptional, (35)
"Did a quick getaway with my kids. Easy to find, clean with everything we needed. Close to Lake George and other stuff to do. Overall it was a great experience"
The price is €154
includes taxes & fees
23 May - 24 May
Adirondack Bungalow Getaway
Fridge, microwave, oven, stovetop
Beautiful cottage on quiet country road walking distance to charming North Creek
9.6 out of 10, Exceptional, (25)
"Beautifully furnished cottage with all you need for a comfortable overnight. Propane fireplace and a comfortable couch make it a perfect after-ski spot."
The price is €203
includes taxes & fees
2 Jun - 3 Jun
Beautiful cottage on quiet country road walking distance to charming North Creek
Beach
Scenic lakefront retreat with water access, private dock, grill, W/D & fireplace
10.0 out of 10, Exceptional, (4)
"I really enjoyed staying the place. "
Scenic lakefront retreat with water access, private dock, grill, W/D & fireplace
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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.

Other types of properties in Chestertown you may be interested in

Water park
Six Flags Lodge & Indoor Waterpark
3.5 star property
7.6 out of 10, Good, (1001)
"Great getaway for the kids. They loved it."
The price is €235
includes taxes & fees
23 May - 24 May
Six Flags Lodge & Indoor Waterpark
Indoor pool
La Quinta Inn & Suites by Wyndham Lake George
2.0 star property
9.0 out of 10, Wonderful, (1220)
"Hotel was very clean and modern Breakfast was buffet and it was as good as that can be , got to love them waffles , Person in charge of breakfast was well organized and kept it all moving Indoor Pool is nice , particularly for kids "
The price is €95
includes taxes & fees
2 Jun - 3 Jun
La Quinta Inn & Suites by Wyndham Lake George
Lobby
The Queensbury Hotel
3.0 star property
9.2 out of 10, Wonderful, (1114)
"great location, excellent food, first-rate staff."
The price is €132
includes taxes & fees
23 May - 24 May
The Queensbury Hotel
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.

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 €154 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?

Scenic lakefront retreat with water access, private dock, grill, W/D & fireplace: This holiday home rental outside 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 4 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 selection of books.

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.

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