Photo by Julie Miller
Chestertown apartments
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Explore Chestertown condo rentals
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Sleeps 6 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
60 reviews(60 reviews)
Luxury Adirondack getaway with 4 private ensuites
Sleeps 16 · 4 bedrooms · 4 bathrooms
9.29.2 out of 10
Wonderfulwonderful
Cozy retreat with fireplace, kayaks, and shared beach/pond access
Sleeps 5 · 2 bedrooms · 1+ bathroom
9.09.0 out of 10
Wonderfulwonderful
16 reviews(16 reviews)
Peaceful Lakeside Retreat with Private Beach
Sleeps 5 · 2 bedrooms · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
17 reviews(17 reviews)
Secluded gem with forest view, beach access & W/D
Sleeps 4 · 1 bedroom · 2 bathrooms
8.08.0 out of 10
Very goodvery good
16 reviews(16 reviews)
Lily Pad South at Loon Lake near Gore Mountain
Sleeps 5 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
47 reviews(47 reviews)
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- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
Are there any apartment holiday rentals in Chestertown?
Choose one of our apartment holiday rentals in Chestertown that let you live more like a local. Town of Horicon, Little Gore Glades and Sagamore Glades are some of the most popular areas to base yourself.
How much does it cost to stay in an apartment holiday rental in Chestertown?
The size of your apartment holiday rental and the number of bedrooms can influence how much you pay. Another thing that can affect the price is the availability of amenities, like a balcony, pool or hot tub. Whether you’re looking for a luxury or a budget-friendly apartment, Stayz will help you find a Chestertown holiday condo rental that fits your budget.
When is the best time to rent a holiday condo in Chestertown?
The most popular month to visit Chestertown is July, so if you’d like to experience this place at its buzziest, consider staying then. Average temperatures at this time of year range from 13ºC to 27ºC. Once you’ve worked out the best time to visit this part of Warren County, Stayz will help you find an apartment holiday rental that comes with a homey atmosphere that traditional hotel rooms can’t match.
Where can I rent a Chestertown holiday apartment with great views?
Stayz has some incredible holiday condo rentals in Chestertown, including properties with views of historic areas. In between seeing the sights, chill out and enjoy vistas that are an attraction in themselves.
Does Chestertown have any weekend apartment rentals?
Turn on the out-of-office message and get away to Chestertown for a weekend of fun in a Stayz apartment holiday rental. Our handy tip? Stay flexible with your preferred dates and book early to get the first choice of the best holiday condo rentals.
Can I book a luxury apartment in Chestertown?
Boasting deluxe amenities like pools and hot tubs, our luxury apartment holiday rentals in Chestertown will take your trip to new heights. They generally come with plush furniture, ultra-modern appliances and lots more. To truly kick back and relax, look for holiday condo rentals that come with hotel-like services such as housekeeping.
What are the top things to do in Chestertown?
Get your Chestertown trip off to an awesome start with a visit to top-rated sights like Lake George, Gore Mountain Ski Resort and Loon Lake Beach. Stay in a Stayz apartment holiday rental with the family and then discover this destination’s wonders together.
Why should I book my apartment holiday rental with Stayz?
With over 2 million holiday rentals to pick from across the world, we help guests find a stay that goes beyond the typical hotel room experience. Whether that’s an ideally located apartment holiday rental or even a boat, you’ll always get the entire place to yourself. What’s more, our Book with Confidence Guarantee and flexible cancellation policies mean you can book stress-free on Stayz.