Chestertown Vacation Rentals, New York: house rentals & more

Select from 62 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.

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Find the best place to stay - Chestertown

Lakefront cabin with beautiful loft, game room, views, private dock

Sleeps 10 · 5 bedrooms · 3 bathrooms

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

Sleeps 6 · 3 bedrooms · 2+ bathrooms

Year round Log Cabin on Loon Lake. Minutes from skiing at Gore Mountain

Sleeps 10 · 5 bedrooms · 3 bathrooms

Top rated rentals - Chestertown

Warrensburg Vacation Rental | 5BR | 4.5BA | 3,000 Sq Ft | Stairs Required

Perfect for families.

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Find out more about Chestertown

Why visit Chestertown

Outdoor Adventures: Chestertown is a haven for outdoor enthusiasts, featuring stunning lakes and relaxing beaches.
Scenic Beauty: The picturesque surroundings and enchanting vibe create a romantic atmosphere.
Historical Exploration: Discover intriguing military museums and charming historical sites in the town.
Cozy Accommodations: Enjoy unique stays in cozy cottages, inviting vacation homes, and distinctive cabins.
Nearby Attractions: Venture to Glens Falls for additional recreational opportunities and breathtaking landscapes.

Popular types of accommodation in Chestertown

Planning a getaway to Chestertown? You're in for a treat! Discover the charm of cozy cottages, houses, and unique accommodations like the Wevertown Barn. Whether you prefer a rustic cabin or a spacious lodge, Chestertown offers diverse options to make your stay memorable. Dive into the local experience and find the perfect rental for your next adventure.

Cabins: The top choice for visitors, cabins in Chestertown offer a cozy retreat surrounded by nature.
Houses: Ideal for families or groups, these homes provide spacious accommodations and a home-like atmosphere.
Caravan Parks: A great option for those seeking a more communal experience with facilities for campers and RVs.
Cottages: Charming and quaint, cottages provide a picturesque getaway in the heart of Chestertown.
Apartments: Convenient and versatile, apartments are perfect for travelers looking for modern amenities.**

Top attractions in Chestertown

Chestertown, New York, is a perfect destination for outdoor enthusiasts and those seeking scenic beauty and romance. Visitors can explore stunning lakes, relaxing beaches, and intriguing military museums, offering a variety of experiences for travelers. Whether you're traveling solo, with family, or as a couple, Chestertown's attractions promise a memorable getaway filled with adventure and relaxation in a picturesque setting.

Lake George: A stunning lake known for its romantic ambiance, beautiful beaches, and outdoor activities. Enjoy scenic views while boating, swimming, or picnicking along its picturesque shores, just 12 miles from Chestertown.
Loon Lake Beach: Located within Chestertown, this charming beach offers a relaxing atmosphere. Perfect for sunbathing and swimming, it’s an ideal spot to unwind and enjoy the beautiful surroundings.
Natural Stone Bridge and Caves: An adventurous destination just 7 miles away, featuring unique geological formations. Explore the caves and hike the trails for an exhilarating outdoor experience.

Things to do recommended for couples

Looking for a romantic getaway in Chestertown? Enjoy skiing together at Gore Mountain Ski Resort, sip fine wines at Adirondack Winery, or embark on an adventure at East Chair Ski Lift. Each spot offers a unique experience perfect for couples seeking fun and romance.

Things to do recommended for families

Your family will love exploring North Creek Ski Bowl Town Park, only 10 miles from Chestertown, for relaxing outdoor fun. Shepard's Beach Park, 16 miles away, offers a serene environment, while Tubby Tubes Company, 20 miles out, guarantees thrilling water adventures for everyone!

Things to do recommended for groups

Experience an exhilarating day at the Adirondack Extreme Adventure Course for ziplining and ropes challenges. Hike the scenic Warren County Nature Trails for stunning views. In the evening, enjoy a performance at the Seagle Music Colony, where culture and entertainment await your group.

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

When traveling with a group, family, pets, or seeking extended stays, it's important to prioritize your specific needs in your search. Here are some helpful Vrbo booking tips to assist you.

Traveling to Chestertown with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor space for group gatherings. Luckily, you can easily filter for these options and more 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 having suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
Taking your pets with you to Chestertown: For many families, a vacation isn't truly complete without their furry companions. If you can relate to this, consider exploring Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer amenities like feeding bowls and beds, ensuring that everyone feels comfortable and at home.
Planning for a long term stay visiting Chestertown: If you're seeking 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 rentals. Don’t forget to include amenities like parking, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Chestertown

Chestertown, New York, offers a delightful blend of outdoor adventures and scenic beauty, perfect for a romantic getaway or a relaxing retreat. Explore the charming town, with its friendly atmosphere and historical sites, or venture to nearby Glens Falls for recreation and stunning landscapes. The area's wooded acres and the enchanting vibe of the eastern shore create a unique upstate magic that will leave you rejuvenated and inspired throughout your vacation.

Lake George: Located 16 miles from Chestertown, Lake George is a vibrant resort town known for its stunning natural beauty and outdoor adventures. Visitors flock to Lake George for activities such as skiing in the winter and enjoying the picturesque lake, parks, and beaches in the warmer months. The area offers a romantic backdrop for couples, with scenic views and charming waterfront dining options. Popular attractions include the Lake George Steamboat Company and various ski resorts that cater to both beginners and seasoned snowboarders.
Brant Lake: Just 3 miles from Chestertown, Brant Lake is a hidden gem that offers a serene escape into nature. This quaint town is perfect for outdoor enthusiasts, with ample opportunities for skiing and hiking in the surrounding mountains. The lake itself is a major attraction, providing a peaceful setting for fishing, kayaking, and picnicking. The scenic views and tranquil atmosphere make Brant Lake an ideal spot for a romantic getaway or a family vacation, where you can immerse yourself in the beauty of the Adirondacks.
Chester Shores: Chester Shores is a charming neighborhood within the Chestertown area, renowned for its outdoor activities and breathtaking scenery. Visitors can enjoy skiing at local resorts and exploring the nearby lakes and beaches. The stunning mountain backdrop enhances the area's appeal, making it a popular destination for couples and families alike. With easy access to nature trails and recreational spots, Chester Shores is perfect for those seeking adventure or simply a peaceful retreat to relax and unwind amidst nature.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	20.3°F (-6.5°C)	Light Rain	Mostly Cloudy	Average	Average
February	22.3°F (-5.4°C)	Light Rain	Mostly Cloudy	Average	Average
March	30.4°F (-0.9°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
April	42.6°F (5.9°C)	Light Rain	Mostly Cloudy	Average	Slightly High
May	55.9°F (13.3°C)	Light Rain	Mostly Sunny	Average	Average
June	63.1°F (17.3°C)	Light Rain	Mostly Sunny	Slightly High	Slightly Low
July	69.1°F (20.6°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	67.1°F (19.5°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
September	60.3°F (15.7°C)	Light Rain	Mostly Sunny	Average	Average
October	48.6°F (9.2°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low
November	36.1°F (2.3°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	27.5°F (-2.5°C)	Light Rain	Mostly Cloudy	Slightly Low	Average

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. You might also discover significant savings by booking an extended stay. To find the ideal Vrbo property that fits your budget, utilize our filters to narrow down your search by price, location, and type of vacation rental.

Save more with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash™ on your booking. Being the planner really pays off! When you join our travel rewards program, One Key, you can immediately access exclusive member savings and earn OneKeyCash™ on qualifying reservations. Sign up today and begin enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform for planning your trips, allowing you to easily create new itineraries, continue from where you last left off, or manage your travel plans. You can view your saved or booked properties organized into categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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 most popular type of vacation rental accommodation in Chestertown?

According to our research, cottages are the most desirable vacation property type in Chestertown. But of course, everyone’s idea of an epic trip isn’t the same. Vrbo has vacation homes of all shapes and sizes, so you’re sure to find your ideal fit.

How much does it cost to rent a vacation rental in Chestertown?

Several things determine what you’ll pay for a vacation rental in Chestertown, like the type of property, length of stay and season. Still, all of our vacation homes have something in common — unbeatable value. Just enter your travel dates to find your ideal match.

How much does it cost to rent a beach house in Chestertown?

The average price for a vacation rental close to the beach in Chestertown depends on when you’re traveling and the size and style of property you’re searching for. You can easily find prices on Vrbo by entering your preferred travel dates and destination. Then use our handy filter tool to choose the number of bedrooms and amenities important to you, like a pool, WiFi and air conditioning.

Are there pet-friendly vacation rentals in Chestertown?

Yes. You’ll have your pick of 80 vacation rentals that cater to pets in Chestertown. Many of our pet-friendly vacation rentals even have an outdoor area for your fur baby to have fun in, complimentary treats, doggie beds and proximity to parks. Apply the “Pets allowed” filter to find your pawfect place on Vrbo.

Can I rent a house with a pool in Chestertown?

Add a whole other level of fun to your vacation by booking your group into one of the 20 houses with a private pool in Chestertown. Use our handy search filter to find the kind of property you want on Vrbo, and then spend carefree days splishing and splashing in a swimming pool that’s only for you.

What are popular rental amenities in Chestertown?

Tennis, a nearby river and a nearby waterfront are the most popular rental amenities in Chestertown. Whether you’re taking to the road solo, with a partner or a group of dear friends, Vrbo can help you find a vacation home that matches your style with all the options you need.

Are there large group vacation rentals in Chestertown?

With 19 properties that can host 10 or more people in Chestertown, you won’t have to cross anyone off the invite list. From family get-togethers to special events like Christmas and birthday parties, Vrbo will help you find a large group rental to suit the occasion.

Are there vacation rentals in Chestertown that welcome kids?

Chestertown has 79 family-friendly vacation rentals to choose from. And discovering a stay that welcomes kiddos is a breeze with our “Properties good for families” filter. Besides having the entire place to yourselves, you’ll have access to amenities and perks like extra bedrooms, private pools and yards.

What are the top attractions for families in Chestertown?

Keeping the kids entertained during your Chestertown vacation is a snap with these leading family-friendly attractions:

Loon Lake Beach
Friends Lake
Loon Lake

Are there one-bedroom vacation rentals in Chestertown?

Yes, Chestertown has seven one-bedroom rentals on offer. Typically located in well-regarded areas due to their smaller size, a one-bedroom vacation property is ideal if you’re getting away with your partner or a pal. And with home comforts like air conditioning and more privacy than a standard hotel, you’ll be able to chill out while exploring this fabulous destination.

Can I find two-bedroom vacation rentals in Chestertown?

Gather your nearest and dearest and enjoy peace, privacy and comfort in one of the 16 two-bedroom vacation properties Chestertown has to offer.

Are there vacation rentals with WiFi in Chestertown?

Chestertown has 42 vacation rentals with WiFi, so you’ll be able to stay connected while on vacation. Simply check the “WiFi” box in our handy search filter for a list of properties with this feature. From streaming movie blockbusters to writing and sending emails, these Vrbo homes make it a breeze to get online.

How can I find vacation rentals with air conditioning in Chestertown?

Chestertown has 53 vacation rentals where you’ll be able to spend your days in air-conditioned comfort. To locate a property on Vrbo that provides this perk, enter your preferred travel dates and use the handy filter tool to select the “air conditioning” box.

How old do you have to be to rent a vacation rental in Chestertown?

The minimum required age is typically 16, 18 or 21. It can change from one property to another on Vrbo, so look at the rules of your chosen Chestertown vacation home before booking your escape.

How long can I rent a vacation rental in Chestertown for?

It all depends on the Chestertown property. To look over a list of options offering extended stays, simply type your dates and number of guests into the Vrbo search page. Enjoy having the place to yourself, along with home comforts like a full kitchen, air conditioning and outdoor spaces to play in. Keep your eyes open for any long-term stays that offer discounted weekly or monthly prices.

Does Vrbo offer discounts for vacation homes in Chestertown?

In Chestertown, you’ll find some fantastic discounts and bargains for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you’re wanting a mini escape or a longer stay, we offer plenty of options to match your style.