Find the best place to stay — Chester

Where to stay around Chester?

Our 2018 property listings offer a large selection of 220 vacation rentals near Chester. From 120 houses to 68 cottages, 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: 37 vacation rentals
  • Saybrook Manor: 38 vacation rentals
  • Old Saybrook Center: 28 vacation rentals
  • Madison Center: 46 vacation rentals
  • Westbrook Center: 54 vacation rentals

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

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:

  • Gillette Castle State Park: 418 vacation rentals
  • Norma Terris Theater: 399 vacation rentals
  • Hammonasset Beach State Park: 839 vacation rentals
  • Harvey's Beach: 904 vacation rentals
  • Connecticut River State Wildlife Area: 89 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 120 houses in Chester. Our other popular types of vacation rentals in Chester include:

  • Cottages: 68 rentals available
  • Apartments: 14 rentals available
  • Condos: 4 rentals available

Can I rent golf rentals in Chester?

Absolutely, HomeAway has 124 golf rentals in Chester. You have also many other possibilities in Chester area, including:

  • Near the ocean rentals: 100 rentals
  • Beach rentals: 90 rentals
  • Waterfront rentals: 49 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with pool in Chester?

Yes, you can select your preferred vacation rental with pool among our 14 vacation rentals with pool available in Chester. Please use our search bar to access the selection of vacation rentals available.

    The Waterfront Setting of Chester is Ready to Explore

    The natural parks and other outdoor surroundings create an inviting atmosphere in Chester. One of the city's many top draws is its theaters. Consider a vacation rental for your stay. Many offer full kitchens and spacious living quarters, along with cable or satellite TV and DVD players to entertain you on a lazy day.

    Attractions In and Around Chester

    First time in Chester and looking for things to do? Visitors searching for nearby cultural experiences can spend an enlightening afternoon at Norma Terris Theater, Goodspeed Opera House or Ivoryton Playhouse. To appreciate the outdoor scene, make time for green spaces such as Plattwood Park, Gillette Castle State Park and Cockaponset State Forest. Activities around the area include Essex Island Marina, Chatfield Hollow State Park and Machimoodus State Park. While you're in the area, stop by Scherer Library of Musical Theatre, Nathan Hale Schoolhouse and Major General Joseph Spencer Memorial. You may also want to visit Rathbun Free Memorial Library, Museum of Fife and Drum or East Haddam Historical Society and Museum.