Photo by Julie Miller

Chestertown vacation rentals

We found 307 vacation rentals — enter your dates for availability

Select from 60 homes, 16 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.

Vacation rentals with weekly discounts - Chestertown

Showing deals for:Jan 16 - Jan 23

Image gallery for Lake George/ Gore / snowmobile trail access NEW HOME

Exterior
9.8 out of 10, Exceptional, (17 reviews)
Exceptional
(17 reviews)

Lake George/ Gore / snowmobile trail access NEW HOME

Warrensburg, NY

8% off
Price is $300
$2,099 for 7 nights
All fees included
Lake George/ Gore / snowmobile trail access NEW HOME

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Chestertown

Why visit Chestertown

  • Outdoor Adventures: Chestertown is a haven for outdoor enthusiasts, offering activities like hiking, fishing, and boating in picturesque settings.
  • Scenic Lakes and Beaches: Relax by the beautiful lakes and beaches, perfect for unwinding and enjoying nature's tranquility.
  • Charming Accommodations: Choose from cozy cabins, charming cottages, and private vacation homes for a comfortable stay.
  • Romantic Getaways: The serene environment and stunning vistas make Chestertown an ideal spot for a romantic escape.
  • Family-Friendly Activities: Enjoy vibrant local attractions and recreational spots suitable for families and children.

Popular types of accommodation in Chestertown

If you're exploring vacation rentals in Chestertown, you'll find a delightful range of options to suit your needs. The most popular choices include houses, cozy cabins, and charming cottages. Whether you're looking for house rentals or Adirondack vacation rentals, Chestertown has something for everyone. Enjoy the comfort and convenience of vacation homes that offer a perfect retreat in this scenic area. Your ideal getaway awaits.

  • Houses: The top choice for visitors, these spacious homes offer a comfortable retreat for families or groups seeking a home-like atmosphere in Chestertown.
  • Cabins: A favorite among nature lovers, these rustic retreats provide a cozy escape surrounded by scenic beauty.
  • Cottages: Charming and quaint, these smaller homes are perfect for couples or solo travelers looking for a peaceful getaway.
  • Apartments: Ideal for those seeking a modern and convenient stay, these rentals offer amenities in a compact space.
  • Chalets: These stylish lodges provide a unique alpine experience, blending comfort with mountain views.**

Top attractions in and around Chestertown

Chestertown, New York, is a charming destination perfect for outdoor enthusiasts and those seeking romantic getaways. Visitors can enjoy stunning scenery at local lakes, beaches, and island resorts. Whether you're looking to relax by the water or explore the great outdoors, Chestertown offers a variety of attractions that cater to your adventurous spirit and desire for serene landscapes.

  • The Sagamore Golf Club: Nestled on its own island, this exclusive resort offers a world-class golfing experience along with stunning views of the Adirondack Mountains, perfect for both avid golfers and those seeking relaxation.
  • Friends Lake: A serene escape within Chestertown, Friends Lake boasts a picturesque beach and scenic surroundings, making it an ideal spot for outdoor activities and romantic getaways.
  • Natural Stone Bridge and Caves: A thrilling adventure awaits at this geological wonder, where visitors can explore breathtaking caves and unique rock formations, perfect for outdoor enthusiasts.

Things to do recommended for couples

Looking for a romantic getaway in Chestertown? Enjoy a cozy day skiing at Gore Mountain Ski Resort, indulge in wine tasting at the Adirondack Winery, or have fun playing mini-golf at Around the World Miniature Golf. Each experience offers a perfect blend of adventure and romance.

Things to do recommended for families

Your family will love the North Creek Ski Bowl Town Park, just 10 miles from Chestertown, perfect for relaxation. Shepard's Beach Park, 16 miles away, offers fun recreational activities, while Huletts Park, 15 miles out, provides a serene escape for everyone to enjoy.

Things to do recommended for groups

Experience the thrill of the Adirondack Extreme Adventure Course, just 10 miles from Chestertown, perfect for adventure seekers. Enjoy a captivating performance at the Seagle Music Colony, located 12 miles away, or catch a family-friendly film at the Strand Theater, 13 miles from town.

*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

If you're planning a trip with a group, family, pets, or looking for extended stays, be sure to use the appropriate filters to prioritize your needs. Here are some helpful booking tips for Vrbo.

  • Traveling to Chestertown with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and many others on Vrbo.
  • Traveling to Chestertown with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with finding age-appropriate features, like a private 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 by their side. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home during your stay.
  • Planning for a long term stay visiting Chestertown: If you're searching for vacation rentals with special offers 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 rental options. 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, New York, offers a delightful blend of outdoor adventures and serene getaways, perfect for a romantic vacation. Surrounded by stunning scenic views, including beautiful river vistas and the charming Otter Valley, this quaint town invites travelers to unwind and explore. Nearby areas provide a vibrant atmosphere for recreation, family-friendly activities, and trendy spots, ensuring a memorable escape for everyone. Enjoy the relaxing vibes and discover the best of Chestertown and its surroundings.

  • Brant Lake: Located 3 miles from Chestertown, Brant Lake is a picturesque city known for its stunning outdoor experiences. Nestled amidst breathtaking scenery, this area is perfect for those seeking a romantic getaway or an adventure in nature. Popular activities include skiing at nearby resorts and exploring the serene lakes and mountains. The local landmarks, such as the lake and beach, provide ideal spots for relaxation and recreation, making Brant Lake a must-visit destination for outdoor enthusiasts.
  • The Glen: The Glen is a charming village located in close proximity to Chestertown, offering a delightful mix of outdoor adventures and scenic beauty. Travelers flock here for its romantic ambiance and opportunities for skiing at local ski fields and resorts. The village is surrounded by beautiful lakes, pristine beaches, and well-maintained parks, making it an excellent spot for family outings or quiet retreats. Whether you're enjoying a leisurely stroll by the water or hitting the slopes, The Glen promises an unforgettable experience.
  • Chester Shores: As a scenic neighborhood near Chestertown, Chester Shores is a delightful escape for those who appreciate outdoor activities and breathtaking landscapes. Visitors are drawn to the area for its romantic atmosphere and the abundance of skiing opportunities at nearby resorts. With nearby lakes, beaches, and mountains, Chester Shores offers a variety of attractions for nature lovers. Whether you're looking to relax at the beach or explore the surrounding trails, this neighborhood provides a perfect blend of tranquility and adventure.

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 a breeze

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that suits your budget, take advantage of our filters to narrow down your options by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire booking. It truly benefits you to take on the planning role. When you join our travel rewards program, One Key, you'll gain access to exclusive discounts and earn OneKeyCash on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your travels. You can start new trips, pick up right where you left off, or easily manage and organize your travel plans. All the properties you've saved or booked are now accessible in the Potential, Upcoming, or Current Trips sections. To explore 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)
  • Dr. Morbid's Haunted House (16.5 mi / 26.6 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 when booking a vacation rental?
When considering a vacation rental in Chestertown, New York, the best area to stay is likely along the shores of Loon Lake. This picturesque neighborhood offers a serene atmosphere and easy access to the water, making it ideal for those seeking relaxation or outdoor activities. The lake provides opportunities for swimming, kayaking, and fishing, allowing guests to fully immerse themselves in the natural beauty of the Adirondacks.

Another great option is the town center area, which is charming and convenient. Staying here puts you close to local shops, restaurants, and community events. The Chestertown Farmer's Market, held during the warmer months, is a delightful place to explore local produce and crafts. Additionally, the nearby North Creek Railroad offers a unique opportunity for scenic train rides through the stunning landscape.

Across these areas, you can find a variety of properties suiting different tastes and budgets, ensuring that you can find a great spot for your getaway.
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 areas for renting a beach house in Chestertown?
For renting a beach house in Chestertown, New York, travelers should consider the scenic areas around Loon Lake and the nearby Schroon Lake. Loon Lake offers a picturesque setting with beach access, where vacation rentals often feature amenities such as private docks, outdoor decks, and fire pits, ideal for enjoying sunny afternoons and evenings by the water. Many properties here provide family-friendly amenities, including spacious yards and direct access to swimming areas.

Schroon Lake, located just a short drive from Chestertown, is another excellent option for beach house rentals. This area is known for its charming waterfront properties, many of which come equipped with modern kitchens, screened porches, and breathtaking lake views. Visitors can expect amenities like kayaks or paddleboards available for guest use, enhancing the lakeside experience. The local atmosphere is relaxed, with options for hiking and outdoor activities nearby.

Additionally, the surrounding Adirondack region offers opportunities for exploration, with beautiful hiking trails and natural attractions, making it great for travelers seeking both relaxation and adventure.
Where are the best Chestertown ski resort rentals?
For the best ski resort rentals near Chestertown, New York, travelers should consider the proximity to the nearby Gore Mountain Ski Resort, located just a short drive away. In Chestertown itself, visitors can find a variety of cozy cabins and chalets that offer a rustic charm and comfortable accommodations. Many of these properties feature amenities such as wood-burning stoves, fully equipped kitchens, and outdoor decks with scenic views of the surrounding Adirondack Mountains, ideal for families or groups looking to enjoy winter sports.

Additionally, the nearby town of North Creek provides further options, with vacation rentals that range from modern condos to traditional mountain lodges. These properties often come with convenient features like ski storage, laundry facilities, and access to communal hot tubs or saunas, enhancing the après-ski experience. The area's picturesque landscapes also offer opportunities for hiking and snowshoeing, making it an attractive destination year-round.

Travelers can also explore local dining options and shops in both Chestertown and North Creek, ensuring a well-rounded experience.
What is the most popular type of vacation rental accomodation in Chestertown?
In Chestertown, vacation houses are the most popular type of rental, with about 55 available throughout the area. These homes typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or larger groups. Many vacation houses also offer outdoor amenities such as decks or patios, allowing guests to enjoy the beautiful natural surroundings. Additionally, there are around 16 cabins and 15 cottages, which provide a more rustic experience and often include cozy wood interiors and scenic views. For those seeking a more compact option, several apartments and condos are available as well, usually equipped with essential amenities for a comfortable stay.
Are there any family house rentals in Chestertown?
In Chestertown, New York, families will find a wide selection of vacation rentals—approximately 90 are available throughout the area. This charming town, located in the Adirondack Mountains, offers a variety of family-friendly homes that cater to different needs and preferences. Many properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor decks or yards great for children to play in.

Travelers can explore nearby attractions such as the stunning Lake George, where boating and swimming opportunities await. The surrounding natural beauty provides excellent hiking trails and outdoor activities, making it an ideal destination for families looking to connect with nature. Additionally, Chestertown is close to charming local shops and restaurants, enhancing the overall experience for visitors.
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 and hot tubs, with around 12 options to choose from. This picturesque town, located in the Adirondack Mountains, provides a serene backdrop for travelers seeking relaxation. Many of these rentals come equipped with private pools, hot tubs, and spacious outdoor areas, great for enjoying the natural beauty of the surroundings.

Travelers can expect amenities like fully equipped kitchens for preparing meals, cozy living spaces, and often access to outdoor decks or patios ideal for entertaining or unwinding after a day of exploring. Some properties may also offer proximity to nearby lakes and hiking trails, adding to the overall appeal of a stay in this charming area.
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 numerous pet-friendly house rentals available, with about 35 options to choose from. These vacation homes often come equipped with amenities that ensure a comfortable stay, such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air. Many properties feature cozy fireplaces, making them ideal for relaxing after a day of exploring the nearby Adirondacks.

The area around Chestertown is known for its natural beauty, and pet-friendly outdoor activities are abundant. Nearby, travelers can enjoy hiking trails in the Adirondack Park, where pets are often welcome on leashes. The Schroon River also offers opportunities for canoeing and fishing, and many vacation rentals provide easy access to these outdoor pursuits, allowing guests to enjoy quality time with their pets in nature.
Are there any remote work vacation rentals in Chestertown?
In Chestertown, New York, there are numerous vacation rentals suitable for remote work, with around 96 options available. This picturesque area, located near the Adirondack Mountains, offers a tranquil environment ideal for productivity. Many of these properties come equipped with essential remote work amenities such as desks, Wi-Fi, and dedicated workspace, including features like desk chairs and computer monitors, ensuring that guests can comfortably manage their work tasks while enjoying their stay.

Travelers can expect a mix of charming cabins and spacious homes that often include cozy living areas, fully equipped kitchens, and outdoor spaces to unwind after a day of work. The serene surroundings also provide opportunities for outdoor activities, including hiking and exploring local lakes, making it easy to balance work and leisure. 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 WiFi, ensuring guests stay connected during their stay. Most rentals also feature fully equipped kitchens, allowing travelers to prepare their own meals. Coffee and tea makers are commonly provided for that morning pick-me-up. Many properties offer patios or outdoor spaces, superb for enjoying the serene surroundings. Additionally, a fireplace is a sought-after amenity, adding warmth and a cozy atmosphere, particularly appealing during the colder months.
When is the best time to visit Chestertown for a vacation rental?
The best time to visit Chestertown for a vacation rental is during the peak summer months of June to August, with July being particularly popular among travelers. This vibrant season attracts families and outdoor enthusiasts who flock to the area to take advantage of the warm weather and the plethora of recreational activities available. Visitors can enjoy hiking, fishing, and kayaking in the beautiful Adirondack Mountains, all while soaking in the stunning natural landscapes.

During these months, average temperatures generally range from the mid-60s to the low 80s Fahrenheit, creating a comfortable environment for outdoor exploration and relaxation by the lake. Chestertown's charming small-town atmosphere comes alive with local events, fairs, and farmers' markets, making it an ideal time for those seeking a lively vacation experience.

For those looking for a more budget-friendly option, consider visiting in November. This month offers a peaceful retreat with fewer tourists, allowing you to enjoy the serene beauty of Chestertown and the surrounding fall foliage. The crisp air and colorful leaves create a picturesque setting great for scenic walks and cozy evenings.

Ultimately, the choice of when to visit Chestertown will depend on your preference for lively summer activities or the quiet charm of late fall exploration.
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?
In Chestertown, visitors can enjoy a range of attractions that highlight the area's natural beauty and local culture. The charming town center features quaint shops and eateries that provide a taste of the local flavor. Outdoor enthusiasts can explore the nearby Schroon Lake, which offers opportunities for swimming, fishing, and boating, making it a popular spot during the warmer months.

The surrounding Adirondack Park provides ample hiking trails, with options suitable for various skill levels, allowing visitors to immerse themselves in the stunning forested landscapes. The nearby Chester Historical Society offers insights into the region's history and culture, while the scenic views from the nearby mountains provide picturesque backdrops for photography and relaxation.

For those seeking winter activities, nearby ski resorts like Gore Mountain are just a short drive away, offering skiing and snowboarding options.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

More Vacation Ideas