Discover a selection of 75 holiday rentals in Chester, NY, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at £ 59 per night, and houses and flats & apartments are popular options for a stay in Chester. Either way, you'll find a rental for everyone's needs.
Destination guide

Friendly Chester will entice you

Learn about the unique charm of Chester with a stay in a holiday home rental. This welcoming and relaxing city is well 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 holiday rental, you'll want to experience everything that makes Chester a one-of-a-kind holiday spot. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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 centre:

  • 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

Travelling to and around Chester

Fly into Newburgh, NY (SWF-Stewart Intl.), the closest airport, located 13.6 mi (21.9 km) from the city centre. 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.

Can I find a vacation rental around Chester?

Yes, our 2020 property listings offer a large selection of 75 vacation rentals near Chester. From 61 houses to 3 flats & 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 Vrbo.

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

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

  • The Rock Sports Complex: 229 vacation rentals
  • Museum Village: 251 vacation rentals
  • Castle Fun Center: 233 vacation rentals
  • Sterling Forest State Park: 211 vacation rentals
  • Boscobel House and Gardens: 176 vacation rentals

But there are many other points of interest around Chester listed on Vrbo UK 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. Vrbo UK has 61 Houses in Chester. Our other popular types of vacation rentals in Chester include:

  • Flats: 3 rentals available
  • Cabins: 5 rentals available
  • Cottages: 5 rentals available

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

Can I find a vacation rental with pool in Chester?

Yes, you can select your preferred vacation rental with pool among our 18 vacation rentals with pool available in Chester. Please use our search bar to access the selection of vacation rentals available.