Cheshire County Holiday Rentals, New Hampshire: Holiday Houses & More

Select from 51 homes, 26 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 Vrbo

Keene which includes a church or cathedral and a city

Find spaces that suit your style

Find the best place to stay - Cheshire County

Secluded chalet on 50 acres at base of Mt Monadnock, near lakes -TESLA charger

Sleeps 12 · 5 bedrooms · 2+ 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, 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:

Monadnock State Park (11.4 mi / 18.4 km)
Shattuck Golf Course (12.7 mi / 20.4 km)
Cathedral of the Pines (18.4 mi / 29.6 km)
Crotched Mountain Ski and Ride Area (20.9 mi / 33.6 km)
Vermont Country Store (21.5 mi / 34.6 km)
Pats Peak (28.9 mi / 46.5 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:

Spofford Lake (8.5 mi / 13.7 km)
Monadnock State Park (11.4 mi / 18.4 km)
Madame Sherri Forest (13 mi / 20.9 km)
Madame Sherris Castle Ruins (13.1 mi / 21.1 km)
Brattleboro Common (15.2 mi / 24.4 km)
Pack Monadnock Mountain (20.8 mi / 33.5 km)

Frequently asked questions

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

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 rental 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. Vrbo has holiday rentals 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 rental in Cheshire County?

Different factors can influence how much you pay for a holiday rental 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 Vrbo. Can't live without a hot tub? Use our filters to choose the amenities and features you want in your rental.

What are popular rental amenities in Cheshire County?

Some of the most popular rental 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, Vrbo holiday properties have the best amenities for making new memories with the people who matter most.

Are there large group holiday rentals 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, Vrbo can help you find a large group rental 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 rentals in Cheshire County?

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

Are there holiday rentals 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 Vrbo and stay connected on your getaway.

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

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

How long can I rent a holiday rental 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 Vrbo holiday properties may also offer weekly or monthly discounts, so you can stick around for longer for less.