Charlestown holiday homes, MD, USA: holiday houses & more

Discover a selection of 7 homes and other holiday rentals in Charlestown that are perfect for your trip. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as Wi-Fi and a washer and dryer. No matter what you're looking for, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Charlestown

Showing deals for:18 Jul - 25 Jul

Welcome to Chesapeake Point! Get ready for you and your loved ones to enjoy the vacation of your DREAMS!

Exceptional

(15 reviews)

Chesapeake Point | Waterfront w/ HOT TUB + Beach!

Elkton, Maryland

7% off

NZ$4,607 per night

includes taxes & fees

Bluffside seating overlooking the Chesapeake Bay

Exceptional

(81 reviews)

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

North East, MD

8% off

NZ$788 per night

includes taxes & fees

Exceptional

(44 reviews)

Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

Perryville, MD

8% off

NZ$553 per night

includes taxes & fees

Exceptional

(22 reviews)

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

Havre De Grace, MD

8% off

NZ$489 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Charlestown

Water View House in Charlestown, MD

Sleeps 8 · 4 bedrooms · 3 bathrooms

Cozy Charlestown Getaway - Steps from the Water with a Kayak, & Paddleboards.

Sleeps 10 · 5 bedrooms · 3 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

Choose a holiday rental for your Charlestown getaway

Learn about the unique charm of Charlestown with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Charlestown

Are you hoping to discover things to do while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Charlestown has to offer. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

Dove Valley Winery (7.7 mi / 12.3 km)
Bulle Rock Golf Course (8.7 mi / 14 km)
Plumpton Park Zoo (9.1 mi / 14.7 km)
Back Creek Golf Club (12.5 mi / 20.2 km)
Paradocx Vineyard (16.1 mi / 26 km)
Wyncote Golf Club (16.5 mi / 26.6 km)

Exploring the natural landscape of Charlestown

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Charlestown. Here are some of the area’s most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

North East Beach Area (5.6 mi / 9 km)
Garrett Island Beach (5.8 mi / 9.3 km)
Millard Tydings Memorial Park (6.7 mi / 10.8 km)
Fair Hill State Natural Resources Management Area (11.9 mi / 19.1 km)
Lewis Park (13.8 mi / 22.2 km)
University of Delaware Botanic Gardens (13.9 mi / 22.3 km)

Transport to and around Charlestown

Fly into Baltimore, MD (MTN-Martin State), the closest airport, located 29.2 mi (47 km) from the city centre.

Frequently asked questions

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

Houses are the most popular style of holiday home in Charlestown, according to our data. Even if you have a different idea about what you’d like, Bookabach has holiday homes in a variety of sizes and shapes. Compare our options to find your perfect Charlestown pad.

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

Length of stay, property type and season are some of the conditions that can influence the price of a holiday home. Simply add your travel dates to find your ideal match. From cosy cabins to sprawling luxury villas, all Bookabach holiday homes provide incredible value.

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

The average price for a holiday home by the beach in Charlestown will depend on when you’ll be there and the style and size of property you’re looking for. You can quickly and easily find prices on Bookabach by entering your destination and preferred travel dates. Then use our filters to select the number of bedrooms and amenities essential to you, like a pool, WiFi and air conditioning.

Are there pet-friendly holiday homes in Charlestown?

There are, yes. You’ll have a choice of three holiday homes that allow pets in Charlestown on Bookabach. Our furry kids need to get away from it all too, so simply use our search function for pet-friendly holiday homes to find a perfect pad where your puppy can join the fun.

What are popular home amenities in Charlestown?

A garden, a nearby river and a swimming pool rank as the most popular home amenities in Charlestown. Whether you’re taking a trip solo, with your spouse or a bunch of friends, Bookabach will help you find a holiday home that matches your style with all the conveniences you’re looking for.

Are there large group holiday homes in Charlestown?

With two Charlestown properties that can accommodate five or more people, you can invite a few extra family members or pals along. Whether you’re planning a casual gathering or a birthday party, we’ll help you book a comfortable space to match the occasion.

Are there holiday homes in Charlestown that welcome kids?

With three family-friendly holiday homes to select from in Charlestown, now is a superb time to introduce the kiddos to the thrills of travel. Just click on our “Properties good for families” filter box to search for stays packed with amenities perfect for holidaying families, such as dining rooms, private pools, bunk beds and entertainment areas.

What are the top attractions for families in Charlestown?

Keep your kids busy at these fantastic family-friendly attractions in Charlestown:

Havre de Grace Maritime Museum
Plumpton Park Zoo
Historical Society of Cecil County

How can I find holiday homes with air conditioning in Charlestown?

There are three holiday homes with air conditioning in Charlestown offering that cool, cool breeze and extra element of comfort. Just enter your dates of travel and then use our filters to help you book stays with air conditioning.

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

The minimum required age is normally 16, 18 or 21. It can vary from one property to another on Bookabach, so check the rules of your chosen Charlestown holiday home before booking.

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

The amount of time you can book a Charlestown holiday home for is up to each property. Just put in your dates of travel to browse available options that offer extended stays. They feature all you need to make your extended holiday more comfortable and convenient, such as kitchens and backyards. Some properties might also offer discounted weekly or monthly prices, so you can have a longer stay for less.