Destination guide

Travel to artsy Chester

Enjoy the theater scene and other features of Chester. One of the city's many top draws is its parks. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities

Activities and attractions in Chester

Are you hoping to find attractions to visit in the area? Venture out of your cozy vacation rental and experience everything that makes Chester a fun place to get away. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Essex Steam Train (5.5 mi / 8.8 km)
  • Chatfield Hollow State Park (6.2 mi / 10 km)
  • Machimoodus State Park (6.8 mi / 10.9 km)
  • Banner Country Club (7.7 mi / 12.4 km)
  • Chamard Vineyards (7.8 mi / 12.6 km)
  • Priam Vineyards (12 mi / 19.3 km)
Natural features

Exploring the natural landscape of Chester

Whether you're an adventurous traveler or just want to take in the scenery, Chester is a great place to get out in nature. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Plattwood Park (2.9 mi / 4.7 km)
  • Gillette Castle State Park (3.1 mi / 5.1 km)
  • Cockaponset State Forest (3.5 mi / 5.6 km)
  • Haddam Meadow State Park (5.3 mi / 8.5 km)
  • Chatfield Hollow State Park (6.2 mi / 10 km)
  • Machimoodus State Park (6.8 mi / 10.9 km)
Transport

Transportation to and around Chester

The nearest airport is in New Haven, CT (HVN-Tweed - New Haven Regional), located 23.2 mi (37.3 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into New London, CT (GON-Groton - New London), which is 23.2 mi (37.4 km) away.

Where to stay around Chester?

Our 2019 property listings offer a large selection of 206 vacation rentals near Chester. From 121 Houses to 59 Bungalows, 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 is the best area to stay when traveling to Chester?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Chester:

  • Niantic: 148 vacation rentals
  • Saybrook Manor: 35 vacation rentals
  • Westbrook Center: 47 vacation rentals
  • Madison Center: 40 vacation rentals
  • Guilford Center: 17 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

Can I rent Houses in Chester?

Yes, of course. HomeAway has 121 Houses in Chester. Our other popular types of vacation rentals in Chester include:

  • Bungalows: 59 rentals available
  • Cabins: 59 rentals available
  • Cottages: 59 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 12 vacation rentals with pool available in Chester. Please use our search bar to access the selection of vacation rentals available.