Find the best place to stay — Chestertown

Where to stay around Chestertown?

Our 2018 property listings offer a large selection of 396 vacation rentals near Chestertown. From 205 houses to 58 cabins, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Chestertown for a holiday or a weekend are on HomeAway.

What are the popular points of interest near where I can stay when traveling to Chestertown?

HomeAway offers a large selection of vacation rentals near lovely places in Chestertown. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Loon Lake Beach: 489 vacation rentals
  • Gore Mountain: 284 vacation rentals
  • Lake George Beach: 422 vacation rentals
  • Adirondack Winery: 429 vacation rentals
  • Million Dollar Beach: 417 vacation rentals

But there are many other points of interest around Chestertown listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent houses in Chestertown?

Yes, of course. HomeAway has 205 houses in Chestertown. Our other popular types of vacation rentals in Chestertown include:

  • Cabins: 58 rentals available
  • Cottages: 39 rentals available
  • Townhomes: 21 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including apartments and more.

Can I rent golf rentals in Chestertown?

Absolutely, HomeAway has 289 golf rentals in Chestertown. You have also many other possibilities in Chestertown area, including:

  • Skiing rentals: 235 rentals
  • Lake rentals: 179 rentals
  • Mountain rentals: 152 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with pool in Chestertown?

Yes, you can select your preferred vacation rental with pool among our 48 vacation rentals with pool available in Chestertown. Please use our search bar to access the selection of vacation rentals available.

    The Lakeside Setting of Chestertown is Ready to Explore

    The lake and forests create a pretty picture of Chestertown. This secluded city is known for its coffeehouses, canoeing and horseback riding. Top attractions in the area include Prospect Mountain, Fort William Henry and Lake George Dog Beach. If you're looking for somewhere to stay with more space, consider a vacation rental—many rental homes offer full kitchens and laundry facilities.

    Attractions In and Around Chestertown

    First time in Chestertown and looking for places to see? Visitors searching for nearby landmarks can take a trip to Fort William Henry. To appreciate the outdoor scene, make time for beaches like Lake George Dog Beach and Loon Lake Beach and green spaces such as Prospect Mountain and Pack Demonstration Forest. Winter activities you might appreciate include visiting Gore Mountain Ski Resort and Hickory Ski Center. Want to take in a game or event? Get tickets for Lake George Forum. Activities around the area include Adirondack Winery, Lake George Shoreline Cruises and Lake George Steamboat Company. Also you might want to add Natural Stone Bridge and Caves, Tannery Pond Community Center or North Creek Ski Bowl Town Park to your agenda.