Cheshire, Connecticut holiday accommodation: short-term house rentals & properties

Scroll through and select from holiday rentals in Cheshire to find one that's perfect for your trip. Holiday rentals offer the best amenities for your family, friends or furry companion, including parking and a garden. What you'll find is a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Cheshire

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Sleeps 2 · 1 bedroom · 1 bathroom

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Delight in the lush landscape of Cheshire

Enjoy the history and other features of Cheshire. Well known for its hiking, waterfalls and shopping, this romantic city won't disappoint. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Cheshire

Are you searching for things to do in the area? Venture out of your cosy holiday rental and experience everything that Cheshire has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

Mount Southington Ski Area (5.1 mi / 8.3 km)
Crystal Bees (8.7 mi / 13.9 km)
Powder Ridge Mountain Park and Resort (8.8 mi / 14.2 km)
Lake Compounce (9 mi / 14.5 km)
Quassy Amusement Park (12.5 mi / 20.1 km)
Yale Golf Course (13.7 mi / 22 km)

Exploring the natural features in Cheshire

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Cheshire is a great place to spend some time outside. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

Hubbard Park (5.1 mi / 8.3 km)
Sleeping Giant State Park (5.4 mi / 8.6 km)
Mount Carmel (5.8 mi / 9.4 km)
Hop Brook Lake (8.3 mi / 13.3 km)
Lake Beseck Beach (9.1 mi / 14.7 km)
Casey Field (10.7 mi / 17.3 km)

Transport to and around Cheshire

The nearest airport is in Oxford, CT (OXC-Waterbury - Oxford), located 12 mi (19.3 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into New Haven, CT (HVN-Tweed - New Haven Regional), which is 16.5 mi (26.6 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Cheshire?

The most sought-after types of holiday homes in Cheshire are houses. Hoping for something different? Stayz has many options to match the diverse needs of our guests, so you'll see properties in all sizes, and for all budgets. The ideal fit is ready and waiting for you — discover yours today.

How much does it cost to rent a holiday home in Cheshire?

Property type, season and length of stay are some factors that can influence the price of a holiday home. Simply enter your dates of travel to find your perfect match. From comfy cabins to sprawling luxury villas, all Stayz holiday homes offer incredible value.

How much does it cost to rent a beach house in Cheshire?

When you travel and the style and size of the property will determine the cost of your beachside holiday home. Click on your Cheshire travel dates to see all your options on Stayz. Did someone just say "hot tub"? Use our filters to choose the features and amenities you want in your holiday home.

What are popular home amenities in Cheshire?

Some of the most popular home amenities guests are looking for in Cheshire are a fireplace, off-street parking options and a dishwasher. Whether you're on the road with buddies, family or even pets, Stayz holiday homes come with the best amenities for fun and relaxation with the people that matter most.

What are the top attractions for families in Cheshire?

Keep the kids happy at these fun family-friendly attractions in Cheshire:

Lake Compounce
Lake Beseck Beach
Cheshire Hollow Farm

How old do you have to be to rent a holiday home in Cheshire?

The minimum age requirements can vary across properties on Stayz, so be sure to look at the rules of the holiday home in Cheshire you want to book. But in general, it's 16, 18 or 21.

How long can I rent a holiday home in Cheshire for?

The length of time you can book a holiday home in Cheshire is down to the property. Simply enter your selected travel dates to display a list of options offering extended stays. With loads of features like kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to get a perfect place to call your home away from home in Cheshire.