Where to stay around Chester, CT?

Our 2018 property listings offer a large selection of 211 vacation rentals near Chester. From 116 Houses to 64 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 VRBO.

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: 108 vacation rentals
  • Old Saybrook Center: 29 vacation rentals
  • Westbrook Center: 52 vacation rentals
  • Madison Center: 36 vacation rentals
  • Saybrook Manor: 35 vacation rentals

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

What are the popular point of interests near where I can stay when traveling to Chester?

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

  • Gillette Castle State Park: 414 vacation rentals
  • Norma Terris Theater: 389 vacation rentals
  • Hyland House Museum: 363 vacation rentals
  • Essex Steam Train: 598 vacation rentals
  • Connecticut River State Wildlife Area: 114 vacation rentals

But there are many other points of interest around Chester listed on VRBO 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 has 116 Houses in Chester. Our other popular types of vacation rentals in Chester include:

  • Bungalows: 64 rentals available
  • Cabins: 64 rentals available
  • Cottages: 64 rentals available

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

Can I find a vacation rental with pool in Chester?

Yes, you can select your prefered vacation rental with pool among our 16 vacation rentals with pool available in Chester. Please use our search bar to access the selection of vacation rentals available.

    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 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)

    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)