Photo by Julie Miller

Chestertown vacation rentals

We found 283 vacation rentals — enter your dates for availability

Select from 60 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.

Vacation rentals with weekly discounts - Chestertown

Showing deals for:Jun 12 - Jun 19

Image gallery for Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing

Living area
10 out of 10, Exceptional, (41 reviews)
Exceptional
(41 reviews)

Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing

Chestertown

10% off
Price is $329
$2,304 for 7 nights
All fees included
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing

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)
  • Magic Forest Park (18.4 mi / 29.6 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, 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.

More Vacation Ideas