Discover a selection of 49 holiday home rentals in Cheshire that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Stayz holiday homes have the best amenities for hanging out with the people that matter most, including internet/WiFi and air conditioning. Prices start at AU$ 191 per night, and holiday houses and flats & apartments are popular options for a stay in Cheshire. Either way, you'll find holiday accommodation for everyone's needs.
Top rated rentals — Cheshire
Destination guide

Head to the historical 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-see attractions in the area. With a holiday 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 holiday home and experience everything that makes Cheshire a one-of-a-kind holiday spot. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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 highlights

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 centre:

  • 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 centre. 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.

How many holiday accommodation are available around Cheshire?

Our 2021 accommodation listings offer a large selection of 49 holiday rentals around Cheshire. From 30 holiday houses to 17 flats & apartments, find unique holiday homes for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Cheshire is on Stayz.