Book Cheshire County holiday rental accommodation: short-term rental properties & homes

Select from 45 homes, 29 cottages and other holiday rentals in Cheshire County to find one that's perfect for your trip. Whether you’re staying in a holiday home with family or friends, you'll have the best amenities for spending time at your home away from home, including air conditioning and Wi-Fi. At the end of the day, you'll be sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Popular Cheshire County destinations on Stayz

Keene showing a city and a church or cathedral

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Cheshire County

View of Loon Lodge from Rear Parking Area

Victorian Lakefront Cottage With Spectacular Sunrise View Of Water

Sleeps 8 · 4 bedrooms

Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!

Sleeps 22 · 8 bedrooms · 5+ bathrooms

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

Book a holiday rental for your Cheshire County getaway

Learn about the unique charm of Cheshire County with a stay in a holiday home rental. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Cheshire County

Are you looking for top things to see and do during your stay? Venture out of your cosy holiday rental and check out everything that makes Cheshire County a fun spot to go on holiday. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

Brentwood Golf Course (3.5 mi / 5.7 km)
Friendly Farm (9.5 mi / 15.2 km)
Walpole Mountain View Winery (10.6 mi / 17.1 km)
Monadnock State Park (11.4 mi / 18.4 km)
Shattuck Golf Course (12.7 mi / 20.4 km)
Harris Hill Ski Jump (15.5 mi / 25 km)

Exploring the natural landscape of Cheshire County

Whether you're looking for fun outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Cheshire County. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

Swanzey Lake (6.2 mi / 10 km)
Chesterfield Gorge Natural Area (6.5 mi / 10.5 km)
Spofford Lake (8.5 mi / 13.7 km)
Granite Lake (9.2 mi / 14.8 km)
Monadnock State Park (11.4 mi / 18.4 km)
Nubanusit Lake (11.6 mi / 18.7 km)

Frequently asked questions

What is the best area to stay in Cheshire County when booking a holiday home?

Stoddard is one of the more desirable areas to secure a holiday home in Cheshire County. Take a look at our relaxing properties and then go out and explore this destination like a local.

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

According to our research, houses are the most in-demand type of property in Cheshire County. But naturally, everyone’s idea of the perfect trip can differ. Stayz has holiday homes in a variety of shapes and sizes, and we’ll help you locate the perfect match.

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

Different factors can influence how much you pay for a holiday home in Cheshire County, like the length of stay, season and type of property. Still, all of our holiday homes have something in common — unbeatable value. Just enter your travel dates to find your home away from home.

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

When you travel and the size and style of the property will help determine the cost of your beachside stay. Enter your Cheshire County travel dates to see your options on Stayz. Can’t live without a hot tub? Use our filters to choose the amenities and features you want in your home.

What are popular home amenities in Cheshire County?

Some of the most popular home amenities people prefer in Cheshire County are a fridge, a microwave oven and off-street parking options. Whether you’re on the road with your besties, family or even pets, Stayz holiday properties have the best amenities for making new memories with the people who matter most.

Are there large group holiday homes in Cheshire County?

With 16 properties that can sleep 10 people or more in Cheshire County, there’s no need to leave anyone off your invite list. From holidays with the extended family to special events like Thanksgiving or Christmas parties, Stayz can help you find a large group home to match the occasion.

What are the top attractions for families in Cheshire County?

You’ll find lots of awesome things to see and do with the family in Cheshire County, including:

Monadnock State Park
Friendly Farm
Cathedral of the Pines

Can I find two-bedroom holiday homes in Cheshire County?

Take off with your loved ones and enjoy peace, privacy and comfort in one of the 17 two-bedroom holiday homes Cheshire County has to offer.

Are there holiday homes with WiFi in Cheshire County?

Whether you’d like to keep up with the news, reply to emails or update your social media accounts, there are 35 holiday homes with WiFi in Cheshire County. Check the “WiFi” box when searching on Stayz and stay connected on your getaway.

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

The minimum age permitted can vary across properties on Stayz, so check the rules of the holiday home in Cheshire County you’re interested in. But normally, it’s 16, 18 or 21.

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

The amount of time you can stay in a Cheshire County holiday home for is down to the property. Simply enter your dates of travel to browse available options offering extended stays. They come with everything you need to make your extended holiday more convenient and enjoyable, such as air conditioning and laundries. Some Stayz holiday properties may also offer weekly or monthly discounts, so you can stick around for longer for less.