Photo by Julie Miller

Chestertown holiday lettings

We found 292 holiday rentals — enter your dates for availability

Select from 60 homes, 19 cottages and other holiday rentals in Chestertown to find one that's perfect for your trip. Whether you're staying in a holiday rental with family or friends, you'll have the best amenities for spending time at your home away from home, which might include parking and a garden. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Chestertown

Showing deals for:3 Jul - 10 Jul

Image gallery for Loon Lake, Chestertown - spotless, bright chalet for 6-8, close to Public Beach

Huge yard for play
10 out of 10, Exceptional, (87 reviews)
Exceptional
(87 reviews)

Loon Lake, Chestertown - spotless, bright chalet for 6-8, close to Public Beach

Chestertown

8% off
Price is £2,227
for 7 nights, 1 chalet
£318 per night
includes taxes & fees
Loon Lake, Chestertown - spotless, bright chalet for 6-8, close to Public Beach

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Head to the secluded city of Chestertown

The lake and forests provide a pleasant backdrop to your holiday home in Chestertown. Travellers to this relaxing city praise the coffee shops, canoeing and horse riding. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Chestertown

Are you hoping to find top things to see and do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Chestertown a fun spot to go on holiday. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • The Sagamore Golf Club (8.2 mi / 13.2 km)
  • Gore Mountain Ski Resort (10.4 mi / 16.7 km)
  • Garnet Hill Lodge and Ski Resort (15.8 mi / 25.5 km)
  • Adirondack Winery (16.3 mi / 26.2 km)
  • Six Flags Great Escape (21.6 mi / 34.7 km)
  • Hiland Golf and Country Club (22 mi / 35.4 km)

Exploring the natural features in Chestertown

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Chestertown is a great place to get outside. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Loon Lake Beach (2 mi / 3.3 km)
  • Friends Lake (2.8 mi / 4.5 km)
  • Loon Lake (3.2 mi / 5.2 km)
  • Natural Stone Bridge and Caves (7 mi / 11.3 km)
  • Schroon Lake (9.6 mi / 15.4 km)
  • Lake George (12.3 mi / 19.9 km)

Travelling to and around Chestertown

Fly into Glens Falls, NY (GFL-Floyd Bennett Memorial), the closest airport, located 23.6 mi (38 km) from the city centre.

Frequently asked questions

What is the best area to stay in Chestertown when booking a holiday rental?
When considering a holiday rental in Chestertown, New York, the charming area surrounding the town centre is an excellent choice. This locality offers a delightful blend of scenic beauty and local character, making it ideal for those looking to immerse themselves in the tranquility of the Adirondacks.

Chestertown is known for its proximity to the stunning Schroon Lake, a popular spot for swimming, kayaking, and fishing during the warmer months. Additionally, the nearby Gore Mountain provides thrilling opportunities for skiing and snowboarding in the winter, drawing outdoor enthusiasts year-round.

The town centre itself features a selection of quaint shops, eateries, and local cafes, allowing visitors to experience the warm hospitality of the region. With a variety of properties available, from cosy cabins to charming cottages, guests can find accommodations that suit their needs and preferences.
How much does it cost to rent a holiday home in Chestertown?
Prices for holiday rentals in Chestertown vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chestertown to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Chestertown holiday house rentals?
You can find great discounts on house rentals in Chestertown on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Chestertown?
For renting a beach house in Chestertown, the area around Lake George is particularly appealing, as it offers a range of properties with scenic waterfront views. The hamlet of Pottersville, located just a short drive from Chestertown, features charming cottages and cabins that often come with private docks, outdoor seating areas, and fire pits, great for enjoying summer evenings by the water.

Nearby, the Lake George Village area provides additional options for holiday rentals, including larger family homes with spacious backyards and amenities such as barbecue grills and game rooms. Many properties here offer easy access to the lake for swimming and boating, with some featuring kayaks or paddleboards for guest use.

In addition, Chestertown itself is surrounded by the stunning natural beauty of the Adirondacks, making it a great base for outdoor activities. Rentals in the area often include access to hiking trails, with some properties located near popular spots for fishing and wildlife watching.
Where are the best Chestertown ski resort rentals?
For the best ski resort rentals near Chestertown, New York, consider the nearby area of Gore Mountain. Located approximately 20 minutes away, this popular ski destination offers a variety of rental options. In Chestertown itself, visitors can find charming cabins and lodges that provide a cozy retreat after a day on the slopes. Many of these properties feature amenities such as fully equipped kitchens, fireplaces, and outdoor decks with scenic views of the surrounding Adirondack Mountains.

In the vicinity of Gore Mountain, you'll also discover an array of holiday rentals, including ski-in/ski-out lodgings and spacious chalets that cater to larger groups or families. These accommodations often come with modern conveniences like Wi-Fi, hot tubs, and game rooms, providing a superb balance of comfort and entertainment.

Chestertown is located among beautiful natural landscapes, offering not just skiing but also opportunities for hiking and exploring the picturesque surroundings. The local community provides access to quaint shops and dining, allowing guests to enjoy the charm of small-town life while being close to outdoor adventures.
What is the most popular type of holiday rental accomodation in Chestertown?
In Chestertown, holiday houses are the most popular type of holiday rental, with about 165 available throughout the area. These houses often feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor spaces for enjoying the picturesque views of the surrounding nature. Many come with amenities such as fireplaces and BBQ grills, making them ideal for families or groups looking for a comfortable retreat.

Additionally, there are approximately 51 charming cottages that provide a quaint, homely atmosphere, great for those seeking a more rustic experience. Cabins, numbering around 36, offer a unique stay in the heart of the Adirondack Mountains, often equipped with cozy interiors and access to beautiful hiking trails.
Are there any family house rentals in Chestertown?
In Chestertown, New York, there are numerous family-friendly house rentals available, with around 84 options to choose from. This charming area is located in the beautiful Adirondack Mountains, providing a superb backdrop for outdoor adventures. Many of these homes feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor decks where families can enjoy the fresh mountain air.

Visitors can explore nearby attractions such as the stunning Lake George and the picturesque hiking trails of the surrounding forests. Properties often include amenities like Wi-Fi, laundry facilities, and sometimes even game rooms or fire pits for evening gatherings.
Can I rent a holiday home with a pool or hot tub in Chestertown?
In Chestertown, there are several holiday homes available for rent that feature pools and hot tubs, with around 12 options to choose from. This picturesque town, located in the Adirondack Mountains, offers a serene getaway for those looking to relax and enjoy nature. Many of these properties come equipped with private pools and hot tubs, making them ideal for families or groups seeking a tranquil retreat. Additionally, amenities such as spacious outdoor decks, fully equipped kitchens, and cosy living areas are commonly found, ensuring a comfortable stay.
Can I find long-stay holiday rentals in Chestertown?
A long-stay holiday rental in Chestertown is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Chestertown?
In Chestertown, there are numerous pet-friendly house rentals available, offering a range of options for travellers with furry companions. Many of these properties feature amenities such as spacious gardens, outdoor decks, and fully equipped kitchens, making them suitable for both relaxation and convenience during your stay.

The area is surrounded by the natural beauty of the Adirondack Mountains, providing ample opportunities for outdoor activities like hiking and exploring. Nearby, the picturesque Loon Lake offers opportunities for swimming and kayaking, where pets are often welcome. Furthermore, the Chestertown area boasts local parks and trails that are great for walking your dog, ensuring that both you and your pet can enjoy the scenic surroundings.
Are there any remote work holiday rentals in Chestertown?
In Chestertown, New York, there are a substantial number of remote work holiday rentals available, with around 264 options to choose from. This picturesque town, located in the Adirondack Mountains, offers a tranquil setting for those looking to combine work and leisure. Many of the properties are equipped with essential amenities for remote work, including high-speed Wi-Fi and dedicated workspaces, ensuring a productive environment.

Travellers can expect a variety of accommodations, ranging from cosy cabins to spacious homes, often featuring comfortable living areas, full kitchens for meal preparation, and outdoor spaces to enjoy the natural surroundings. The area is known for its stunning landscapes, with opportunities for hiking, fishing, and enjoying the local wildlife, making it an ideal location for a work-cation. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chestertown holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Chestertown with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Chestertown?
In Chestertown, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals. Many properties also offer onsite parking for convenience. Outdoor spaces, such as decks or patios, provide a lovely setting for relaxation amidst the picturesque surroundings. Additionally, you can expect amenities like coffee and tea makers for those early morning brews, and fireplaces that create a warm, inviting atmosphere during cooler evenings.
When is the best time to visit Chestertown for a holiday rental?
The best time to visit Chestertown for a holiday rental is during the peak season from June to August, with July being the most popular month among travellers. This vibrant period attracts outdoor enthusiasts eager to take advantage of the warm weather, with plenty of opportunities for hiking, kayaking, and exploring the stunning natural beauty of the Adirondacks.

During these summer months, visitors can expect pleasant temperatures averaging between 15 to 25 degrees Celsius, great for enjoying the local lakes and picturesque scenery. The town also comes alive with community events and the chance to connect with both locals and fellow travellers, creating a lively option that enhances your holiday experience.

For those looking to save a bit, November offers a quieter alternative. While it may be less bustling, this month presents a unique charm with the tranquility of early winter setting in, allowing for peaceful walks amidst the crisp air and the chance to enjoy the serene landscapes without the crowds.

Whether you're drawn to the excitement of summer activities or the calm of the shoulder season, Chestertown has something special to offer throughout the year.
How early should I book a Chestertown holiday rental?
Book your Chestertown holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Chestertown?
In Chestertown, visitors can enjoy a variety of attractions that highlight the area's natural beauty and outdoor activities. The stunning Schroon Lake is a major draw, offering opportunities for swimming, fishing, and boating, with several waterfront parks for picnicking and relaxation. The nearby Hudson River is superb for canoeing and kayaking, making it a great spot for water enthusiasts.

The charming town itself features quaint shops and local eateries, providing a taste of the community's hospitality. For those interested in hiking, the surrounding Adirondack Mountains offer numerous trails with breathtaking views, including the nearby Pharaoh Mountain Wilderness Area, which is popular for its scenic vistas and diverse wildlife.
Can I change or cancel my Chestertown home rental booking on Vrbo?
To find Chestertown holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Chestertown holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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