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Chestertown holiday lettings

We found 301 holiday rentals — enter your dates for availability

Select from 61 homes, 17 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.

Holiday rentals with weekly discounts - Chestertown

Showing deals for:28 Nov - 5 Dec

Image gallery for Elizabeth. A Guest House Near Lake George.

Exterior
8.2 out of 10 rating
Very good
(45 reviews)

Elizabeth. A Guest House Near Lake George.

Chestertown, NY

12% off
Price is £2,357
£337 nightly
Includes taxes & fees
Elizabeth. A Guest House Near Lake George.

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Find out more about Chestertown

Find out more about Chestertown

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)
  • 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)

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 best area to stay in Chestertown when booking a holiday rental?
When considering a holiday rental in Chestertown, New York, the area surrounding the town centre is an excellent choice. This picturesque neighbourhood offers a charming small-town atmosphere, making it ideal for visitors looking to immerse themselves in the local culture. Staying here puts you within easy reach of delightful shops, cafes, and restaurants, providing a great base for exploring the town.

One of the top attractions nearby is the stunning Loon Lake, which is great for a day of relaxation by the water, swimming, or enjoying a picnic. Additionally, the scenic Adirondack Park is just a short drive away, offering a wealth of outdoor activities such as hiking, fishing, and stunning vistas. There are a variety of holiday rental properties available in this area, suiting different preferences and budgets, ensuring that you're likely to find something that suits your needs.
How much does it cost to rent a holiday home in Chestertown?
Prices for holiday 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 holiday 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?
In Chestertown, New York, the best areas for renting a beach house are primarily around the beautiful shores of Lake George, which is just a short drive away. The area surrounding the northern part of the lake, especially in places like Hague and Ticonderoga, offers a variety of holiday rentals. Many of these properties provide stunning lake views and direct access to the water, making them ideal for swimming, kayaking, or simply enjoying the scenic surroundings.

Travellers can expect amenities such as private docks, outdoor seating areas, and fire pits, great for evening gatherings by the lake. Some properties may also include spacious decks, BBQ grills, and fully equipped kitchens, allowing guests to prepare meals while taking in the natural beauty of the area.
Where are the best Chestertown ski resort rentals?
For skiing in the Chestertown area, the nearby Gore Mountain Ski Resort is a popular choice, located just a short drive away. In Chestertown itself, travellers can find a range of holiday rentals, including cosy cabins and larger family homes, which often come equipped with essential amenities such as fully stocked kitchens, fireplaces, and spacious living areas, creating a warm and friendly space after a day on the slopes.

Properties in the Chestertown vicinity frequently feature outdoor spaces, such as decks or patios, where guests can relax and take in the beautiful winter landscape. Many of these rentals are also conveniently located near local shops and eateries, providing easy access to dining options and supplies.
What is the most popular type of holiday rental accomodation in Chestertown?
In Chestertown, holiday houses are the most popular type of accommodation, with approximately 58 available throughout the area. These houses are often set in picturesque surroundings, providing a tranquil retreat for visitors. Most include amenities such as fully equipped kitchens, spacious living areas, and outdoor decks or patios where guests can enjoy the beautiful natural scenery.
Are there any family house rentals in Chestertown?
In Chestertown, New York, there is a substantial selection of family-friendly houses, with around 97 options available for those seeking a getaway. This charming town, located in the heart of the Adirondacks, provides a serene atmosphere superb for families. Many of these rentals offer spacious living areas, full kitchens ideal for preparing family meals, and outdoor spaces superb for children to play and explore.

Visitors will find properties equipped with conveniences such as Wi-Fi, laundry facilities, and often outdoor grills for summer barbecues. The area is known for its natural beauty, nearby lakes, and recreational opportunities, making it easy to engage in activities like hiking, fishing, or simply enjoying a day by the water.
Can I rent a holiday home with a pool or hot tub in Chestertown?
In Chestertown, New York, there are several holiday homes available for rent that feature pools and hot tubs, with around 12 options to choose from. This charming town, located in the heart of the Adirondacks, offers a serene escape surrounded by nature. Many of these properties come equipped with private pools and inviting hot tubs, providing the superb setting for relaxation after a day of outdoor activities.
Can I find long-stay holiday rentals in Chestertown?
A long-stay holiday rental in Chestertown is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Chestertown?
In Chestertown, there are numerous pet-friendly house rentals available, with around 36 options for travellers to consider. This charming town, located in the heart of the Adirondack Mountains, provides a lovely setting for those looking to enjoy the great outdoors with their pets. Many holiday rentals here come equipped with amenities such as spacious backyards, fully equipped kitchens, and cozy living areas, making them ideal for families or groups.
Are there any remote work holiday rentals in Chestertown?
In Chestertown, New York, there are a variety of remote work holiday rentals available, with around 103 options to choose from. This picturesque town, located in the Adirondack Mountains, offers a serene environment great for working remotely. Many properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated workspaces, and comfortable desk setups, ensuring a productive atmosphere. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chestertown holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Chestertown with parking available—perfect for families or travellers 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 holiday rental amenities include fully equipped kitchens, which typically feature essential appliances such as microwaves and refrigerators. Guests can expect cookware, dishware, and utensils provided, making it easy to prepare meals during their stay. This focus on kitchen facilities allows visitors to enjoy a more homely experience while exploring the natural beauty of the surrounding area.
How early should I book a Chestertown holiday rental?
Book your Chestertown holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Chestertown home rental booking on Vrbo?
To find Chestertown holiday 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 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 travellers 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 cosy 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 holiday 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.

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