Photo by Julie Miller

Chestertown vacation rentals

We found 291 vacation rentals — enter your dates for availability

Select from 59 homes, 19 cottages, and other vacation rentals in Chestertown to find one that's perfect for your trip. Whether you're staying in a vacation rental with your kids or with friends, you'll have the amenities you expect and more, which might include a fireplace and a washer and dryer. You're sure to find a rental for everyone's needs, including options that are accessible or non-smoking.

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Find out more about Chestertown

Why visit Chestertown

  • Outdoor Adventures: Chestertown is ideal for outdoor enthusiasts, offering activities like hiking, fishing, and boating in its beautiful natural surroundings.
  • Romantic Getaways: Perfect for couples, the town provides serene lakeside spots and charming accommodations for a romantic escape.
  • Scenic Neighborhoods: Explore picturesque areas like Bolton Landing and the Central Leatherstocking region, showcasing stunning landscapes.
  • Cozy Accommodations: Enjoy a range of lodging options, from private vacation homes to inviting cabins and cottages.
  • Family-Friendly Fun: Chestertown offers a variety of family activities, making it a great destination for all ages.

Popular types of accommodation in Chestertown

Planning a getaway to Chestertown? You’ll find a variety of cozy accommodations to suit your needs, from charming houses to inviting cabins and seasonal cottages. Explore our selection of Chestertown vacation rentals and discover the perfect spot for your Adirondack adventure. With options designed for comfort and relaxation, you can enjoy a memorable stay with us at Vacasa.

  • Houses: These spacious homes are the top choice for travelers seeking comfort and privacy during their stay in Chestertown.
  • Cabins: Ideal for those who love the outdoors, these rustic retreats offer a cozy atmosphere surrounded by nature.
  • Cottages: Quaint and charming, cottages provide a warm and inviting space for a peaceful getaway.
  • Apartments: Convenient and often centrally located, apartments are perfect for those looking for a home-away-from-home experience.
  • Chalets: Offering a unique blend of luxury and rustic charm, chalets are a delightful option for a mountain escape.**

Top attractions in and around Chestertown

Chestertown, New York, is a perfect destination for outdoor enthusiasts and couples seeking a romantic getaway. With its stunning lakes, beautiful beaches, and charming island resorts, visitors can enjoy a variety of scenic experiences. Whether you're looking to relax by the water or explore the natural beauty of the area, Chestertown offers a diverse range of attractions that cater to those who appreciate nature and adventure.

  • Friends Lake: Nestled in Chestertown, Friends Lake offers a serene escape with its picturesque scenery, perfect for outdoor activities. Enjoy romantic lakeside strolls or relax on the beach, immersing yourself in nature's tranquility.
  • Loon Lake Beach: This charming beach invites you to unwind and soak up the sun. With its inviting waters, Loon Lake Beach is ideal for swimming and enjoying a laid-back day by the lake.
  • The Sagamore Golf Club: Located 8 miles from Chestertown, this stunning island resort features a world-class golf course set against breathtaking landscapes, making it a must-visit for golf enthusiasts.

Things to do recommended for couples

Chestertown offers a charming getaway for couples. Enjoy a peaceful hike in the nearby Adirondack Mountains or take a scenic kayak trip on the Schroon River. Don't miss a candlelit dinner at a local restaurant, where you can savor delicious cuisine in a cozy atmosphere.

Things to do recommended for families

In Chestertown, families can explore the scenic trails of the Adirondacks, enjoy a day at the nearby Lake George, and visit local farms for seasonal activities. Kids will love the hands-on experiences at the Chestertown Farmer's Market during summer weekends.

Things to do recommended for groups

Explore the scenic beauty of the Adirondacks with a group hike on nearby trails, or enjoy a fun-filled day at the Chestertown Farmers Market, where you can taste local produce and crafts. Don’t miss the opportunity for a group canoeing adventure on the tranquil Schroon River.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Chestertown

When planning your trip—whether you're traveling with a group, family, pets, or seeking longer accommodations—be sure to prioritize your preferences when filtering your options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Chestertown with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Chestertown with young kids: Traveling with young children can be quite demanding. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Chestertown: For many families, a vacation wouldn’t feel complete without their furry companion. If that resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chestertown: If you're searching for vacation rentals that offer special rates for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in and around Chestertown

Chestertown offers a serene escape with its stunning natural features, perfect for outdoor enthusiasts and couples seeking romance. Explore the scenic neighborhoods surrounding the town, including the charming Bolton Landing and the picturesque Central Leatherstocking region. With acres of lush property and a relaxing vibe, Chestertown is an ideal base for family-friendly adventures and trendy recreation. Discover the perfect blend of tranquility and excitement as you immerse yourself in this beautiful part of New York.

  • Bolton Landing: Located 10 miles from Chestertown, Bolton Landing is a charming lakeside community known for its stunning scenery and romantic atmosphere. Outdoor enthusiasts flock to this area for its golf courses and private country clubs, making it a perfect spot for both relaxation and recreation. Visitors can enjoy breathtaking views of the lake, explore nearby islands, or unwind at the local beach. Bolton Landing offers a serene escape, ideal for couples and families alike, with plenty of opportunities to connect with nature.
  • Brant Lake: Just 3 miles from Chestertown, Brant Lake is a picturesque destination that captivates travelers with its outdoor adventures and scenic beauty. This city is a haven for skiing enthusiasts, featuring top-notch ski fields and resorts that attract winter sports lovers. In the warmer months, visitors can bask on the sandy beach, hike the surrounding mountains, or enjoy a leisurely day by the lake. Brant Lake's idyllic setting makes it a popular spot for romantic getaways or family vacations filled with fun and excitement.
  • Chester Shores: Nestled around Chestertown, Chester Shores is a delightful neighborhood that offers the perfect blend of outdoor adventures and scenic vistas. This area is particularly appealing to those seeking a romantic escape, with opportunities for skiing and exploring ski resorts during the winter season. The nearby lakes and mountains provide a stunning backdrop for outdoor activities, while urban parks offer a space for relaxation and leisure. Chester Shores is an excellent choice for nature lovers looking to enjoy the beauty of the Adirondacks.

Best time to go to Chestertown

If you're planning a trip to Chestertown, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January20.3°F (-6.5°C)Light RainMostly CloudyAverageAverage
February22.3°F (-5.4°C)Light RainMostly CloudyAverageAverage
March30.4°F (-0.9°C)Light RainMostly CloudyAverageSlightly Low
April42.6°F (5.9°C)Light RainMostly CloudyAverageSlightly Low
May55.9°F (13.3°C)Light RainMostly SunnyAverageAverage
June63.1°F (17.3°C)Light RainMostly SunnySlightly HighSlightly High
July69.1°F (20.6°C)Light RainMostly SunnySlightly HighSlightly High
August67.1°F (19.5°C)Light RainMostly SunnySlightly HighSlightly High
September60.3°F (15.7°C)Light RainMostly SunnyAverageAverage
October48.6°F (9.2°C)Light RainMostly CloudySlightly LowSlightly Low
November36.1°F (2.3°C)Light RainMostly SunnySlightly LowAverage
December27.5°F (-2.5°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Also, opting for a longer stay can lead to significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We're here to help you find the best options for your needs.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or manage your travel arrangements with ease. You can easily access properties you've saved or booked, now organized into Potential, Upcoming, or Current Trips. To explore your Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Head to the remote city of Chestertown

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

Sightseeing in and around Chestertown

Are you searching for attractions to visit while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Chestertown a one-of-a-kind vacation spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Top of the World Golf Course (16.9 mi / 27.2 km)
  • Six Flags Great Escape (21.6 mi / 34.7 km)

Exploring the natural features in Chestertown

Whether you're an active traveler or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Chestertown. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • 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)

Traveling 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 center.

Frequently asked questions

What is the best area to stay in Chestertown, New York, United States of America when booking a vacation rental?
When considering a vacation rental in Chestertown, New York, the area around the charming town center is an excellent choice. This neighborhood offers a delightful mix of convenience and local charm, making it easy to explore the town's attractions. One of the top highlights nearby is the beautiful Loon Lake, great for swimming, fishing, and enjoying picturesque views. Additionally, the nearby Chestertown Farmer's Market offers a wonderful opportunity to sample local produce and crafts, providing a taste of the community's spirit.

Another appealing option is the area surrounding the Schroon River, where you can enjoy scenic walks and outdoor activities. The river's tranquil setting is ideal for kayaking and canoeing, offering a relaxing way to immerse yourself in the natural beauty of the region. With a variety of vacation rentals available, you'll find options that cater to different preferences, from cozy cabins to larger homes great for families.
How much does it cost to rent a vacation home in Chestertown?
Prices for vacation 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 vacation 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 Chestertown ski resort rentals?
For ski resort rentals near Chestertown, travelers should focus on the nearby Gore Mountain area, which is just a short drive away and offers a variety of rental options suitable for winter sports enthusiasts. In the town of North Creek, which is close to Gore Mountain, visitors can find cozy cabins and chalets that cater to groups and families. These properties often come with amenities such as fireplaces, full kitchens, and outdoor decks, great for relaxing after a day on the slopes.

In Chestertown itself, there are charming log homes and rustic lodges that provide a more secluded experience. These rentals frequently feature large living spaces, hot tubs, and proximity to cross-country skiing trails, making them ideal for those looking to enjoy both downhill and Nordic skiing. Many properties also offer easy access to local dining options and grocery stores, enhancing convenience for travelers.

For outdoor enthusiasts, the surrounding area provides numerous opportunities for snowshoeing and winter hiking, with trails that showcase the region's natural beauty. Accommodations in this area often emphasize comfort and warmth, ensuring a cozy retreat after a day of outdoor activities.
What is the most popular type of vacation rental accomodation in Chestertown?
In Chestertown, vacation houses are the most popular type of rental, with around 55 available throughout the charming town. These houses often provide ample space, featuring multiple bedrooms and fully equipped kitchens, making them ideal for families or large groups seeking comfort and convenience. Many of these homes also include outdoor areas for relaxation and enjoying the scenic natural surroundings. In addition to vacation houses, there are about 17 cottages and 12 cabins, which offer a cozy, rustic experience superb for those wanting to immerse themselves in the Adirondack atmosphere. While condos and apartments are available, they are less common compared to the aforementioned options.
Are there any family house rentals in Chestertown?
In Chestertown, New York, visitors can find a wide selection of family-friendly house rentals, with approximately 84 options available. The area is known for its beautiful natural surroundings, particularly near the stunning Lake George, which is superb for outdoor activities such as swimming, fishing, and hiking. Many of these homes boast spacious living areas, full kitchens for preparing family meals, and outdoor decks or patios where guests can enjoy the fresh mountain air.

Properties in the Chestertown vicinity often feature amenities like game rooms, cozy fireplaces, and private yards, making them ideal for families seeking both comfort and fun. Additionally, the nearby Adirondack Mountains provide a wealth of recreational opportunities, including hiking trails and scenic views.
Can I rent a vacation home with a pool or hot tub in Chestertown?
In Chestertown, there are several vacation homes available for rent that feature pools or hot tubs, with around 12 options to choose from. This picturesque town is located in the heart of the Adirondacks, offering a serene backdrop for a relaxing getaway. Travelers can find rentals that include private pools and hot tubs, great for unwinding after a day of outdoor adventures. Many properties also come equipped with amenities such as spacious living areas, full kitchens, and outdoor decks, providing a comfortable setting for families or groups. Find your rental in Chestertown with a pool or a hot tub.
Can I find long-stay vacation rentals in Chestertown?
A long-stay vacation rental in Chestertown is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Chestertown?
In Chestertown, there are a variety of pet-friendly house rentals available, with approximately 36 options for travelers looking to bring their furry friends along. Many of these vacation rentals are situated near the picturesque Adirondack Mountains, providing a serene backdrop for outdoor adventures. Expect amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can play. Some properties may also feature features like fire pits or decks, superb for enjoying the beautiful surroundings.

The area offers easy access to local parks and trails, making it ideal for pet owners who enjoy hiking and exploring nature. Nearby, the Chester Town Park provides open spaces and walking paths, allowing pets to enjoy the great outdoors. See all pet-friendly rentals in Chestertown.
Are there any remote work vacation rentals in Chestertown?
In Chestertown, New York, there are plenty of remote work vacation rentals available, with about 88 options for those looking to blend work and leisure. This scenic town, located in the Adirondack Mountains, offers a tranquil environment ideal for remote work. Many properties come equipped with reliable internet services, including both Wi-Fi and third-party internet options, ensuring that you can stay connected while enjoying the beautiful surroundings.

Travelers can expect amenities such as comfortable workspaces, free Wi-Fi in rooms, and some rentals even allow events, making them suitable for gatherings or meetings. The natural beauty of the area, combined with the charm of Chestertown, provides a great backdrop for a productive stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chestertown vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Chestertown with parking available—perfect for families or travelers 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, which allow travelers to prepare their own meals during their stay. Many vacation rentals also offer onsite parking for added convenience. Guests can enjoy the fresh air and beautiful views from decks or patios, superb for relaxation or outdoor dining. Additionally, properties often feature cozy fireplaces, providing warmth and a charming atmosphere during colder months. Coffee and tea makers are also commonly available, ensuring that guests can enjoy their favorite hot beverages at their leisure.
When is the best time to visit Chestertown for a vacation rental?
The peak travel season in Chestertown occurs from June to August, making it an ideal time for those seeking outdoor adventures and a vibrant setting. July, in particular, draws many visitors who relish the warm summer temperatures, typically ranging from the mid-50s to mid-80s Fahrenheit, superb for kayaking on the serene waters of Lake George or hiking the scenic trails in the surrounding Adirondack Mountains.

During these summer months, Chestertown comes alive with activities such as local festivals, farmers markets, and community events that highlight the charm of this quaint town. Travelers can enjoy long days filled with sunshine, making it convenient to explore the nearby natural wonders and partake in summer sports.

For those looking for a more budget-friendly option, November presents a wonderful opportunity to experience Chestertown's tranquil beauty. While the summer crowds have dispersed, the fall foliage offers stunning views and a peaceful atmosphere, superb for leisurely hikes or cozy moments by the fire.

Ultimately, the best time to book a vacation rental in Chestertown hinges on your preferences. If you're eager for lively summer activities and warm weather, June to August is your go-to. However, if you appreciate a serene escape and the beauty of autumn, November is a delightful choice.
How early should I book a Chestertown vacation rental?
Book your Chestertown vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Chestertown, New York, United States of America?
In Chestertown, visitors can enjoy a variety of attractions that highlight the area's natural beauty and outdoor activities. The charming town is located near the stunning Schroon Lake, where travelers can partake in swimming, fishing, and kayaking during the warmer months. The surrounding Adirondack Mountains offer ample opportunities for hiking, with several trails suiting different skill levels, providing breathtaking views of the landscape.

For those interested in history, the Chestertown Museum showcases the local heritage with exhibits that reflect the town's past. The nearby Gore Mountain is a popular destination for winter sports enthusiasts, offering skiing and snowboarding during the winter season.
Can I change or cancel my Chestertown home rental booking on Vrbo?
To find Chestertown vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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