Owner Direct Vacation
Rentals in Chestertown
The Best Owner Direct Vacation Rentals in Chestertown. Explore thousands of vacation home rentals, large cabins, and villas near Chestertown
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Explore the Best Chestertown Vacation Homes
Looking for the perfect place to stay in Chestertown? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Chestertown character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
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What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Chestertown
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Popular Neighborhoods for Chestertown Vacation Rentals
What are the best areas to stay in Chestertown
Discover the top neighborhoods in Chestertown and choose a place that suits your stay.
Sunday Feb 8
Chestertown, New York
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Chestertown vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Chestertown
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How to Reserve Your Chestertown Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
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Check photos, reviews, and features for your top picks.
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Chestertown Vacation Rental FAQs
1. What are the top vacation rentals in Chestertown?
There are a lot of options in Chestertown. If you plan on staying in the Chestertown area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chestertown:
- Eagles Nest at Loon Lake near Gore Mountain
- TRIPP LAKE RETREAT sleeps 7 and is a great place to make Adirondack memories!
- Secluded and Cozy Townhome at Tripp Lake
- Loon Lake, Chestertown - Spotless, bright chalet, sleeps 6-8, 13 mi. to ski Gore
- Welcome home!
- The Roost, a lakefront 4 season home in the Adirondack Mountains
- The Fern Lodge
- Relax at Our River Retreat
- Rustic Adirondack Retreat on Tripp Lake
- Lakefront home steps away from a private, gentle sloping sandy beach & fire pit.
2. How many vacation rentals have private pools in Chestertown?
There are 1 vacation rentals with private pools near Chestertown. Top-rated homes that have access to a swimming pool include:
3. Which vacation homes in Chestertown are best for families?
If you are looking for a family-friendly vacation home in Chestertown, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chestertown:
4. How many vacation rentals are available in Chestertown?
Currently, the total number of properties listed in 2026 is over 173 in the Chestertown area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chestertown.