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Chestertown Holiday Rentals

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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
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
10.0 out of 10, Exceptional, (63)
"Beautiful mountain views"
The price is AU$323
per night
19 May - 20 May
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
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
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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
Beach
Adirondack Creekside Cottage-Sportmen’s Delight
10.0 out of 10, Exceptional, (36)
"Stay was good"
Adirondack Creekside Cottage-Sportmen’s Delight
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 AU$1,060
per night
22 May - 23 May
Secluded retreat. Great for families. Walk to Trout lake. High Speed Internet.
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 AU$248
per night
22 May - 23 May
Adirondack Bungalow Getaway
Property grounds
Private Chalet In NW Bay With 25 Foot Dock!!
10.0 out of 10, Exceptional, (103)
"Our family booked the chalet for Christmas and the hosts had the place looking very festive which was lovely. The place was exactly what we were after. Mother nature didn’t give us a white Christmas but we loved our stay and Bolton Landing is a gorgeous town. We loved our stay."
Private Chalet In NW Bay With 25 Foot Dock!!
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
Fridge, microwave, oven, stovetop
Lake George Great Location with Lake Access
10.0 out of 10, Exceptional, (8)
"Since booking our stay, Peter was very helpful and hospitable with our trip to Lake George. Everything from restaurant recommendations to making himself available if we needed anything. The property was VERY clean and comfortable and within a short walk to the water. My girlfriend and I would recommend this property without question. Thank you Peter!"
Lake George Great Location with Lake Access
Property grounds
Get away to the Adirondacks, heated Pool open, hot tub on deck.
10.0 out of 10, Exceptional, (49)
"Hot tub is awesome. Love that it is available year round. Great place to unwind and enjoy with family/friends."
Get away to the Adirondacks, heated Pool open, hot tub on deck.
Fridge, microwave, oven, stovetop
Cabin, lake and moose...OH MY!!
10.0 out of 10, Exceptional, (25)
"Perfect place to stay. Clean and cozy. Thank you ."
The price is AU$613
per night
15 May - 16 May
Cabin, lake and moose...OH MY!!
Outdoor dining
Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail
10.0 out of 10, Exceptional, (79)
"Just what we needed for the sides of our group. Phenomenal views."
Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail
Exterior
Private child-friendly home with game room, high-speed WiFi, and wraparound deck
9.8 out of 10, Exceptional, (47)
"Clean property. Kids enjoyed games in basement."
Private child-friendly home with game room, high-speed WiFi, and wraparound deck
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!
Exterior
Handcrafted mountain cabin with gorgeous views
9.8 out of 10, Exceptional, (29)
"Perfect cozy getaway. Peaceful!"
The price is AU$318
per night
16 May - 17 May
Handcrafted mountain cabin with gorgeous views
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
Exterior
Modern Lakeside Cabin - 2 Kayaks, 2 SUPS, perfect lake stay
9.8 out of 10, Exceptional, (93)
"Property was extremely clean and Tom was so helpful since I booked. Would definitely stay here again."
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 AU$537
per night
16 May - 17 May
Charming cabin with three river-view decks & private setting
Exterior
Log Cabin on the Hudson
9.8 out of 10, Exceptional, (83)
"Stayed the weekend with a group of friends and had a great time, would recommend"
Log Cabin on the Hudson
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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.

Chestertown Holiday Home Travel Info

Number of holiday homes
27
Popular accommodation
Chestertown private holiday homes
Known landmarks
Loon Lake Beach, Natural Stone Bridge and Caves and Friends Lake
International airport
Albany, NY (ALB-Albany Intl.)

Other types of properties in Chestertown you may be interested in

Lobby
The Queensbury Hotel
3.0 star property
9.2 out of 10, Wonderful, (1113)
"Lovely hotel with helpful friendly staff. Quiet with good beds."
The price is AU$191
per night
20 May - 21 May
The Queensbury Hotel
Interior
Holiday Inn Resort Lake George - Adirondack Area, an IHG hotel
3.0 star property
9.2 out of 10, Wonderful, (1001)
"No coffee in lobby for the cost of hotel it should be free and available not only in mornings "
The price is AU$227
per night
19 May - 20 May
Holiday Inn Resort Lake George - Adirondack Area, an IHG hotel
Indoor pool
La Quinta Inn & Suites by Wyndham Lake George
2.0 star property
9.0 out of 10, Wonderful, (1209)
"Excellent pool area"
The price is AU$156
per night
19 May - 20 May
La Quinta Inn & Suites by Wyndham Lake George
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, 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 favourite 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 depend 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 AU$248 per night. Entering your travel dates in the search wizard might find you 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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