Calvert County holiday rentals

We found 258 holiday rentals — enter your dates for availability

Select from 98 homes, 32 cottages and other holiday rentals in Calvert County to find one that's perfect for your trip. Holiday rentals offer the best amenities for your family, friends or furry companion, such as a pool and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Popular Calvert County destinations on Stayz

Chesapeake Beach

Chesapeake Beach

Find spaces that suit your style

  • 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

Choose a holiday rental for your Calvert County getaway

Learn about the unique charm of Calvert County with a stay in a holiday home rental. This city has something for everyone. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Calvert County

Are you searching for attractions to see while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Calvert County a one-of-a-kind holiday spot. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Running Hare Vineyard (5.3 mi / 8.5 km)
  • Perigeaux Vineyards and Winery (8.1 mi / 13 km)
  • Chesapeake Beach Water Park (10.9 mi / 17.5 km)
  • Fridays Creek Winery (12.6 mi / 20.3 km)
  • Port of Leonardtown Winery (17.4 mi / 28 km)
  • Maryland International Raceway (18.8 mi / 30.2 km)

Exploring the natural landscape of Calvert County

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Calvert County is a great spot to appreciate mother nature. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Battle Creek Cypress Swamp Sanctuary (4.4 mi / 7.1 km)
  • Matoaka Beach (5.2 mi / 8.4 km)
  • Breezy Point Beach (6 mi / 9.7 km)
  • Cove Point Beach (13.1 mi / 21.1 km)
  • Annmarie Sculpture Garden and Arts Center (13.8 mi / 22.2 km)
  • Upper Yough River (14.7 mi / 23.6 km)

Frequently asked questions

What is the best area to stay in Calvert County when booking a holiday home?
One of the more sought-after areas for a Calvert County holiday home is Rose Haven. When you book your Stayz holiday home, you can look forward to having the entire place to yourselves. This means you won’t have to share it with anyone apart from your people.
What is the most popular type of holiday home accommodation in Calvert County?
Houses are the most popular type of holiday home in Calvert County, according to our data. Even if you’ve got something bigger or smaller in mind, Stayz has holiday homes in a variety of shapes and sizes. Explore our options to find your perfect fit.
How much does it cost to rent a holiday home in Calvert County?
The average price for a holiday home in Calvert County is determined by a number of factors, including property type, season and length of stay. Whether you’d like a sprawling villa with lots of space or a cosy cottage just enough for two, just add your dates of travel to view some great-value stays.
How much does it cost to rent a beach house in Calvert County?
When you travel and the size and style of the property will determine the cost of your beachside escape. Click on your Calvert County travel dates to see your options on Stayz. Can’t live without a private pool? Use the filters to choose the features and amenities you need.
What are popular home amenities in Calvert County?
A microwave oven, a fridge and off-street parking options are rated the most popular home amenities in Calvert County. Whether you’re taking a trip by yourself, with your better half or a group of family members, Stayz can help you find a holiday home that suits your tastes with a load of extras you’ll love.
Are there large group holiday homes in Calvert County?
With eight properties that can host 10 or more guests in Calvert County, you won’t have to hold back on your invites. From holidays with the extended family to special events like birthday and Christmas parties, Stayz can help you find a large group home to suit the occasion.
What are the top attractions for families in Calvert County?
Keeping the kiddos entertained during your stay in Calvert County is a snap with these family-friendly attractions:

  • Chesapeake Beach Water Park
  • Calvert Cliffs State Park
  • Breezy Point Beach

Can I find two-bedroom holiday homes in Calvert County?
Calvert County has 21 two-bedroom holiday homes for you to pick from. Find a holiday home with all the privacy and space you’re looking for at an attractive price on Stayz.
Are there holiday homes with WiFi in Calvert County?
You’ll find 52 holiday homes with WiFi in Calvert County. If you want to disconnect from the world during your escape, but still want to be connected to the internet, these properties are for you. Narrow your search by applying the WiFi filter on Stayz.
How old do you have to be to rent a holiday home in Calvert County?
You should check with the Calvert County holiday home you want on Stayz as age restrictions differ. However, it’s generally 16, 18 or 21.
How long can I rent a holiday home in Calvert County for?
The length of time you can book a holiday home in Calvert County depends on the property. Simply enter your selected dates to see a list of options offering extended stays. With plenty of amenities such as washing machines and kitchens, as well as some offering discounted weekly or monthly prices, you’re sure to discover the perfect place to call your home away from home in Calvert County.

Explore destinations around Calvert County

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