The Glen holiday rentals, Chestertown: holiday houses & more

Scroll through and select from holiday rentals in The Glen to find one that's perfect for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll have the amenities that you expect and more, which might include Wi-Fi and a washer and dryer. At the end of the day, you're sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Find the best place to stay - The Glen

Terrace on the Lake, Spectacular Large Home with Private Beach

Sleeps 20 · 8 bedrooms · 6+ bathrooms

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Top rated rentals - The Glen

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Winter Carnival

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Enjoy full kitchens, pools, gardens and more
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More space, more privacy, more amenities — more value

Find the perfect holiday rental for your The Glen getaway

Learn about the unique charm of The Glen with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in The Glen

Do you want to discover top things to see and do in the city? Venture out of your holiday home and experience everything that makes The Glen a fun spot to go on holiday. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

Gore Mountain Ski Resort (9.5 mi / 15.3 km)
The Sagamore Golf Club (9.9 mi / 15.9 km)
Adirondack Winery (13.3 mi / 21.3 km)
Dr. Morbid's Haunted House (13.4 mi / 21.6 km)
Revolution Rail Co. (10.4 mi / 16.7 km)
Around the World Miniature Golf (13.7 mi / 22 km)

Exploring the natural features in The Glen

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, The Glen is a great place to spend some time outside. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

Friends Lake (3.1 mi / 4.9 km)
Loon Lake Beach (5.5 mi / 8.9 km)
Loon Lake (6.5 mi / 10.5 km)
Prospect Mountain (12.4 mi / 20 km)
Lake George Steamboat Company (13.7 mi / 22 km)
Lake George Dog Beach (13.8 mi / 22.2 km)

Travelling to and around The Glen

The nearest airport is in Glens Falls, NY (GFL-Floyd Bennett Memorial), located 21.2 mi (34 km) from the city centre.

Frequently asked questions

What is the most popular type of holiday rental accommodation in The Glen?

According to our data, cottages are the most popular holiday rental type in The Glen. But that goes without saying, everyone's idea of the perfect stay is bound to be different. Vrbo has holiday rentals with every shape, size and budget in mind, and we'll help you find your ideal match.

How much does it cost to rent a holiday rental in The Glen?

Season, property type and length of stay are some of the things that can influence the price of a holiday home. Simply enter your dates of travel to find your perfect fit. From homey country cottages to plush villas, all Vrbo holiday rentals offer incredible value.

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

The average price for a holiday home near the beach in The Glen depends on when you're going and the size and style of property you're searching for. Find prices easily on Vrbo by entering your travel dates. Then use our filter tool to choose the number of bedrooms and amenities that you need, like air conditioning, WiFi and a pool.

Are there large group holiday rentals in The Glen?

Take your pick of two Vrbo holiday properties in The Glen that can host a group of five or more people. You'll enjoy all the space and privacy you need to kick back with your loved ones — and no one else.

How old do you have to be to rent a holiday rental in The Glen?

Age restrictions can differ between properties on Vrbo, so be sure to check the rules of the holiday home in The Glen you're interested in. But normally, it's 16, 18 or 21.

How long can I rent a holiday rental in The Glen for?

The amount of time you can rent a The Glen holiday home for is up to the property. Just tap in your dates of travel to see available options that offer long-term stays. They include everything you need to make your extended break more convenient and comfortable, like air conditioning and kitchens. Some holiday homes might also offer discounted weekly or monthly prices, so you can hang around longer for less.