Photo by Julie Miller

Chestertown holiday rentals

We found 314 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Select from 60 homes, 15 cottages and other holiday rentals in Chestertown to find one that's perfect for your trip. Whether you're staying in a holiday rental with family or friends, you'll have the best amenities for spending time at your home away from home, which might include parking and a garden. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Head to the secluded city of Chestertown

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

Sightseeing in and around Chestertown

Are you hoping to find top things to see and do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Chestertown a fun spot to go on holiday. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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 outdoor enthusiast or just want to spend some time taking in the scenery, Chestertown is a great place to get outside. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Loon Lake Beach (2 mi / 3.3 km)
  • Friends Lake (2.8 mi / 4.5 km)
  • Loon Lake (3.2 mi / 5.2 km)
  • Lake George (12.3 mi / 19.9 km)
  • Prospect Mountain (15.9 mi / 25.7 km)
  • Shepard's Beach Park (16.4 mi / 26.3 km)

Travelling 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 centre.

Frequently asked questions

What is the most popular type of holiday home accommodation in Chestertown?

The most sought-after types of holiday homes in Chestertown are houses. Want something different? Vrbo has many options to match the unique needs of our guests, so you'll see holiday properties in all shapes and sizes, and for all budgets. The perfect fit is waiting for you — lock in yours today.

How much does it cost to rent a holiday home in Chestertown?

The average price for a holiday home in Chestertown can vary depending on factors like time of year, length of stay and property type. Whether you prefer a sprawling villa with space for the whole family or a cosy cabin for just you and the kids, just enter your dates of travel to see stays that offer great value.

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

When you travel and the style and size of the property will determine the cost of your beachside holiday home. Put in your Chestertown travel dates to see all your options on Vrbo. Can't live without a private pool? Use our filters to select the features and amenities you want.

Are there pet-friendly holiday homes in Chestertown?

You're in luck. There are. Take your pick of 14 stays that welcome pets in Chestertown on Vrbo. Our furry companions also need a break, so simply use our search function for pet-friendly holiday homes to find a pad where Rover can join the fun.

What are popular home amenities in Chestertown?

Tennis, an electric car charging station and nearby museums rank as the most popular home amenities in Chestertown. Whether you're travelling alone, with your significant other or a group of dear friends, Vrbo will help you find a holiday home that matches your tastes with all the features you're looking for.

Are there large group holiday homes in Chestertown?

Chestertown has six holiday properties that can fit 10 or more guests. These stays come with all the space you need to enjoy good times with your favourite people.

Are there holiday homes in Chestertown that welcome kids?

With 14 family-friendly holiday homes available in Chestertown, now is a great time to introduce the kids to the joys of travel. Simply click on our "Properties good for families" filter to discover stays that feature amenities ideal for families on the move, such as living rooms, pools, entertainment units and bunk beds.

What are the top attractions for families in Chestertown?

You'll find loads of cool things to do and see with the family in Chestertown, such as:

  • Loon Lake Beach
  • Natural Stone Bridge and Caves
  • Friends Lake

Are there holiday homes with WiFi in Chestertown?

Chestertown has four holiday homes with WiFi, so you'll be able to stay connected while on holiday. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with your family to posting pics on social media, these Vrbo homes make it easy to go online.

How can I find holiday homes with air conditioning in Chestertown?

Chestertown has 13 holiday homes where you can relax and recharge in air-conditioned comfort. To book a property on Vrbo featuring this amenity, choose your travel dates and use the convenient filters to select the "air conditioning" box.

How old do you have to be to rent a holiday home in Chestertown?

You should check with the Chestertown holiday property you'd like on Vrbo as the age limit differs. However, it's normally 16, 18 or 21.

How long can I rent a holiday home in Chestertown for?

The length of time you can book a holiday home in Chestertown depends on the property. Just enter your chosen travel dates to look at a list of options offering extended stays. With many creature comforts like full kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to discover a perfect place to call your home away from home in Chestertown.

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