Choose from 6 vacation rentals located in Chestertown, New York. Top filters in Chestertown include TV, Dishwasher, and Garden. Prices range from $101 to $797 per night. Our most popular vacation rental types near Chestertown are Hotel and RV.

Top vacation rentals in Chestertown

Life is about who you spend your time with.  In the great room - only smiles!
4.3
Excellent(3 Reviews)
Condo
 in Chestertown
Luxury Group Rental sleeps 12-16
16 guests · 4 bedrooms · 5 baths
Garden · Kitchen / Kitchenette · Air conditioner

Business stays, family stays, couples stay, getaway vacation, and rental in Chestertown at Luxury Group Rental sleeps 12-16 for $285 for your next trip.

$$$$
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Exterior
4.0
Good(36 Reviews)
House
 in Chestertown
Elizabeth. A Guest House Near Lake George.
18 guests · 6 bedrooms · 3 baths
Garden · Pool · Pets allowed

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Chestertown, at $492 per night for your next great vacation.

$$$$
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Property view
4.8
Outstanding(10 Reviews)
House
 in Chestertown
Historic Greek Revival style home w/ screened in porch -near attractions!
11 guests · 6 bedrooms · 5 baths
Garden · Pool · Kitchen / Kitchenette

Nestled in Chestertown, this House is perfect for your next vacation. Enjoy Historic Greek Revival style home w/ screened in porch -near attractions!'s top-rated amenities, including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Nature lodge
 in Chestertown
6 Bed 5 Bath Holiday home in Lake George,Adirondack
Garden · Kitchen / Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to Chestertown? This Nature lodge offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Chestertown

Chestertown travel guide

Let us help you plan your perfect Chestertown vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Chestertown, and more.

Frequently asked questions

What is the price range for rentals in Chestertown?

Vacation rentals in Chestertown have a price range between $101-$797. The average price for rentals in Chestertown is $255 per night.

What are the top things to do in Chestertown, NY?

Chestertown, NY is a great destination for a relaxing and enjoyable getaway. Here are some of the top things to do in Chestertown:

  • Visit the Adirondack Interpretive Center
  • Go hiking in the many beautiful forests
  • Go fishing at the nearby lakes
  • Take a relaxing boat ride on Lake George

With so much to do and explore, Chestertown is the perfect place to spend a weekend or go on a longer vacation.

What are the most popular vacation rental amenities in Chestertown, NY?

The most popular vacation rental amenities in Chestertown, NY include:

  • Fully-equipped kitchens
  • Laundry facilities
  • Private balconies or patios
  • Access to swimming pools
  • High-speed internet

These amenities allow visitors to enjoy all the comforts of home while on vacation. Fully-equipped kitchens offer the convenience of preparing meals in the comfort of the rental. Laundry facilities are also available, allowing vacationers to pack light and do laundry during their stay. Private balconies or patios offer great views of the surrounding area and provide a quiet spot to relax. Swimming pools are also available to enjoy in the warmer months. High-speed internet allows vacationers to stay connected and enjoy all their favorite streaming services.

Where is Chestertown, NY?

Chestertown, NY is a small hamlet located in the northern part of Warren County, in the Adirondack Mountains region of New York. It is situated on the Schroon River, and is known for its beautiful views and outdoor activities. It is home to a small population of about 1,000 people.

What are the best neighborhoods to visit in Chestertown, NY?

The best neighborhoods to visit in Chestertown, NY are:

  • The Chestertown Historic District
  • The Chestertown Marina
  • The Chestertown Beach

These neighborhoods offer a variety of activities, including sightseeing, shopping, and outdoor recreation.

What are the popular shopping destinations in Chestertown, NY?

Chestertown, NY is home to a variety of popular shopping destinations. Here are some of the most popular spots:

  • The Chestertown Mall
  • Chestertown Antique Mall
  • Chestertown Outlet Center
  • Chestertown Shopping Plaza

These shopping spots offer a wide variety of items, from clothing to furniture, making them popular destinations for locals and visitors alike.

Is Chestertown, NY safe to travel to?

Chestertown, NY is generally a safe place to travel to. Here are some safety tips for visitors:

  • Be aware of your surroundings and trust your instincts.
  • Avoid walking alone at night.
  • Stay in well-lit areas and be aware of people around you.

What is the culture like in Chestertown, NY?

Chestertown, NY is a small town located in the Adirondacks, and is known for its friendly and welcoming culture. Here are five points that sum up the culture in Chestertown:

  • The townspeople are genuinely kind and hospitable.
  • The local community is close-knit and supportive.
  • The town celebrates its history with various events throughout the year.
  • The town is filled with outdoor activities for all ages.
  • The town prides itself on its small-town charm.

Where can I find affordable accommodation in Chestertown, NY?

Chestertown, NY offers a variety of affordable accommodations, including the following:

  • The Chestertown Inn
  • The Chestertown Motel
  • The Chestertown Hotel
  • The Chestertown Bed & Breakfast

The Chestertown Inn is a great option for travelers seeking a comfortable and affordable stay. Located in the heart of Chestertown, it offers a variety of amenities, including a full-service restaurant, an outdoor pool, and complimentary Wi-Fi. The Chestertown Motel provides guests with a clean and comfortable stay at a great value. It features an outdoor pool, free Wi-Fi, and a complimentary continental breakfast. The Chestertown Hotel is a luxurious option for those looking for a more upscale experience. It offers a variety of amenities, including an indoor pool, a fitness center, and a full-service restaurant. Finally, the Chestertown Bed & Breakfast is a charming and cozy option for travelers seeking a unique stay. It features a variety of amenities, including complimentary breakfast, free Wi-Fi, and a cozy lounge area.

How can I get around in Chestertown, NY?

To get around in Chestertown, NY, you can:

  • Rent a car
  • Take a taxi
  • Walk or bike around

What are the must-visit tourist attractions in Chestertown, NY?

Chestertown, NY is home to many great tourist attractions, including the renowned Lake George, the historic Fort Ticonderoga, and the beautiful Adirondack Mountains. Other must-visit attractions in Chestertown include:

  • The Great Escape & Splashwater Kingdom
  • The House of Frankenstein Wax Museum
  • The Natural Stone Bridge and Caves
  • The Adirondack Animal Land
Chestertown is a great destination for any traveler looking to explore the area's natural and historic beauty.

What do I need to know before visiting Chestertown, NY?

Before visiting Chestertown, NY, it's important to know the following things:

  • The town is located in the Adirondack Mountains of New York State
  • It's an ideal spot for outdoor activities such as camping, hiking, fishing, and boating
  • There are plenty of historical sites in the area, such as the Chestertown Historic District and the Chestertown Historic Church

The town is also home to a variety of restaurants, shops, and galleries, making it a great place to explore and experience the local culture. Additionally, the town has a wide range of lodging options, from cozy bed and breakfasts to spacious cabins.

What are the most popular vacation rental amenities in Chestertown?

  • TV
  • Dishwasher
  • Garden

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