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 highlights

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)

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 2020 accommodation listings offer a large selection of 84 holiday lettings near Chester. From 61 Houses to 2 Condos/Apartments, find unique self catering accommodation for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay near Chester is on HomeAway.

What are the most popular points of interest and landmarks to stay near when travelling to Chester? offers a large selection of holiday accommodations near great places in Chester. From travellers, the most popular points of interest to stay near are:

  • Museum Village: 265 holiday lettings
  • Castle Fun Center: 245 holiday lettings
  • The Golf Club at Mansion Ridge: 267 holiday lettings
  • Hudson Highlands Nature Museum: 221 holiday lettings
  • Demarest Hill Winery: 186 holiday lettings

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

Can I rent Houses in Chester?

Yes, of course. offers 61 Houses in Chester. Our other popular types of Chester holiday rentals include:

  • Condos/Apartments: 2 self catering accommodations
  • Cabins: 8 self catering accommodations
  • Cottages: 8 self catering accommodations

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

Can I find a holiday accommodation with pool in Chester?

Yes, you can select your preferred holiday accommodation with pool among our 19 holiday homes with pool available in Chester. Please use our search bar to access the selection of holiday rentals available.