Destination guide

Friendly Chester will entice you

Learn about the unique charm of Chester with a stay in a private vacation home. This welcoming and relaxing city is known for its shopping, restaurants and skiing. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.


Activities and attractions in and around Chester

Are you looking for things to do while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Chester a one-of-a-kind vacation spot. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Castle Fun Center (1.8 mi / 2.8 km)
  • Goshen Historic Track (5 mi / 8 km)
  • The Golf Club at Mansion Ridge (5.1 mi / 8.2 km)
  • Tuxedo Ridge Ski Center (7.1 mi / 11.5 km)
  • Mount Peter Ski Area (7.4 mi / 12 km)
  • Brotherhood Winery (7.5 mi / 12 km)
Natural features

Exploring the natural features in Chester

Whether you're looking for adventure or just want to take in the scenery, Chester is a great place to get outside. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • The Rock Sports Complex (1.1 mi / 1.8 km)
  • Arrow Park Lake and Lodge (6 mi / 9.7 km)
  • Mary H Harriman Memorial Park (6.4 mi / 10.4 km)
  • Thomas Bull Memorial Park (9 mi / 14.4 km)
  • Lake Tiorati Beach (10.1 mi / 16.3 km)
  • Sterling Forest State Park (10.5 mi / 16.8 km)
How to get there

Traveling to and around Chester

Fly into Newburgh, NY (SWF-Stewart Intl.), the closest airport, located 13.6 mi (21.9 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Caldwell, NJ (CDW-Essex County), which is 32.8 mi (52.7 km) away.

Where to stay around Chester?

Our 2019 property listings offer a large selection of 92 vacation rentals near Chester. From 63 Houses to 3 Condos/Apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Chester for a holiday or a weekend are on HomeAway.

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

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

  • Museum Village: 289 vacation rentals
  • Castle Fun Center: 267 vacation rentals
  • Mountain Creek Ski Resort: 200 vacation rentals
  • Bear Mountain State Park: 385 vacation rentals
  • United States Military Academy: 152 vacation rentals

But there are many other points of interest around Chester 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 Chester?

Yes, of course. HomeAway has 63 Houses in Chester. Our other popular types of vacation rentals in Chester include:

  • Condos/Apartments: 3 rentals available
  • Cabins: 11 rentals available
  • Cottages: 11 rentals available

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

Can I find a vacation rental with pool in Chester?

Yes, you can select your preferred vacation rental with pool among our 23 vacation rentals with pool available in Chester. Please use our search bar to access the selection of vacation rentals available.

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