Destination guide

Head to the historic city of Cheshire

Enjoy the history and other features of Cheshire. This romantic city is known for its hiking, waterfalls and shopping. Lake Compounce and East Rock Park are just a couple of the must-sees in the area. With a vacation rental, you get a home away from home—many rentals offer full kitchens and outdoor grills for some home cooking.


Sightseeing in and around Cheshire

Do you want to find things to do while you're in the area? Venture out of your vacation home and experience everything that makes Cheshire a one-of-a-kind vacation spot. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Lake Compounce (9 mi / 14.4 km)
  • Cheshire Hollow Farm (2.4 mi / 3.9 km)
  • Mount Southington Ski Area (4.9 mi / 7.9 km)
  • Sleeping Giant Golf Course (5.2 mi / 8.4 km)
  • Tradition Golf Club at Wallingford (7.5 mi / 12.1 km)
  • Hunter Memorial Golf Course (7.6 mi / 12.3 km)
Natural features

Exploring the natural landscape of Cheshire

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Cheshire is a great place to get outside. These are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • East Rock Park (11.9 mi / 19.2 km)
  • Drazen Orchards (1.5 mi / 2.4 km)
  • Bartlem Park (1.6 mi / 2.6 km)
  • Quinnipiac Recreation Area (2.4 mi / 3.9 km)
  • Roaring Brook Park (2.7 mi / 4.3 km)
  • Habershon Field (4 mi / 6.4 km)
How to get there

How to get to and around Cheshire

The nearest airport is in Oxford, CT (OXC-Waterbury - Oxford), located 12.4 mi (19.9 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into New Haven, CT (HVN-Tweed - New Haven Regional), which is 16.8 mi (27.1 km) away.

Where to stay around Cheshire?

Our 2019 property listings offer a large selection of 21 vacation rentals near Cheshire. From 15 Houses to 2 Condos/Apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Cheshire for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Cheshire?

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 Cheshire:

  • Litchfield: 161 vacation rentals
  • Devon / Walnut Beach: 31 vacation rentals
  • Madison Center: 37 vacation rentals
  • Momauguin: 21 vacation rentals
  • Portland: 23 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 Cheshire?

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

  • Barker Museum: 114 vacation rentals
  • Roaring Brook Park: 152 vacation rentals
  • Cheshire Hollow Farm: 105 vacation rentals
  • Quinnipiac Recreation Area: 122 vacation rentals
  • Maplecroft Plaza Shopping Center: 145 vacation rentals

But there are many other points of interest around Cheshire 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 Cheshire?

Yes, of course. HomeAway has 15 Houses in Cheshire. Our other popular types of vacation rentals in Cheshire include:

  • Condos/Apartments: 2 rentals available
  • Cabins: 2 rentals available
  • Cottages: 2 rentals available

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

Can I find a vacation rental with internet/wifi in Cheshire?

Yes, you can select your preferred vacation rental with internet/wifi among our 16 vacation rentals with internet/wifi available in Cheshire. Please use our search bar to access the selection of vacation rentals available.

    Explore destinations around Cheshire