Cheshire County Vacation Rentals, New Hampshire: house rentals & more

Select from 52 homes, 26 cottages, and other vacation rentals in Cheshire County to find one that's perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll have the best amenities for spending time at your home away from home, which might include cable TV and a washer and dryer. Whatever you're looking for, you'll be able to choose a rental that has what everyone needs, including a place that is accessible or non-smoking.

Popular Cheshire County destinations on Vrbo

Keene featuring a city and a church or cathedral

Find spaces that suit your style

House

Condo/Apartment

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

Top rated rentals - Cheshire County

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Book a vacation rental for your Cheshire County getaway

Experience the unique character of Cheshire County with a stay in a vacation home rental. There's no shortage of things to see and do in the area.If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Cheshire County

Are you looking for attractions to see while you're in the area? Venture out of your cozy vacation rental and check out everything that makes Cheshire County a fun place to get away. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

Monadnock State Park (11.4 mi / 18.4 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)
Newport Golf Club (29.1 mi / 46.8 km)

Exploring the natural landscape of Cheshire County

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Cheshire County is a great place to get out in nature. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city center:

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 vacation rental?

Stoddard is one of the more desirable areas to secure a vacation 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 vacation 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 vacation 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 vacation rental in Cheshire County?

Different factors can influence how much you pay for a vacation rental in Cheshire County, like the length of stay, season and type of property. Still, all of our vacation 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 vacation properties have the best amenities for making new memories with the people who matter most.

Are there large group vacation 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 vacations 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 vacation rentals in Cheshire County?

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

Are there vacation 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 vacation 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 vacation rental in Cheshire County?

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

How long can I rent a vacation rental in Cheshire County for?

The amount of time you can stay in a Cheshire County vacation 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 vacation more convenient and enjoyable, such as air conditioning and laundries. Some Vrbo vacation properties may also offer weekly or monthly discounts, so you can stick around for longer for less.