Charlestown holiday lettings

We found 146 holiday rentals — enter your dates for availability

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.

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, 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:

  • Bulle Rock Golf Course (8.7 mi / 14 km)
  • Plumpton Park Zoo (9.1 mi / 14.7 km)
  • Paradocx Vineyard (16.1 mi / 26 km)
  • Wyncote Golf Club (16.5 mi / 26.6 km)
  • Dove Valley Winery (7.7 mi / 12.3 km)
  • Mount Felix Vineyard & Winery (8.1 mi / 13 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)
  • Fair Hill State Natural Resources Management Area (11.9 mi / 19.1 km)
  • Lewis Park (13.8 mi / 22.2 km)
  • Glen Cove (13.8 mi / 22.2 km)
  • University of Delaware Botanic Gardens (13.9 mi / 22.3 km)

Transport to and around Charlestown

Fly into Wilmington, DE (ILG-New Castle), the closest airport, located 21.3 mi (34.2 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Baltimore, MD (MTN-Martin State), which is 29.2 mi (47 km) away.

Frequently asked questions

How much does it cost to rent a holiday home in Charlestown?
Prices for holiday rentals in Charlestown vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Charlestown to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Charlestown holiday house rentals?
You can find great discounts on house rentals in Charlestown on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Charlestown?
In Charlestown, holiday houses are the most popular type of holiday rental, with about 18 available throughout the area. These houses typically offer spacious layouts, multiple bedrooms, and amenities such as fully equipped kitchens and outdoor areas, making them ideal for families or groups looking to enjoy a relaxing getaway. Additionally, there are several cottages and apartments scattered around, providing more options for those seeking a cozier or more compact accommodation.
Are there any family house rentals in Charlestown?
In Charlestown, Maryland, there are several family-friendly holiday rentals available, making it a great choice for those travelling with children. Properties in this charming area often feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where kids can enjoy fresh air and play. Many homes also come with amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay for all guests.

Located near the Chesapeake Bay, visitors can easily access beautiful waterfront parks and recreational activities, superb for family outings. The nearby Elk Neck State Park offers hiking trails and picnic spots, allowing families to immerse themselves in nature.
Can I rent a holiday home with a pool or hot tub in Charlestown?
In Charlestown, Maryland, there are several holiday homes available for rent that feature pools or hot tubs, providing excellent options for travellers seeking relaxation during their stay. The area offers a variety of rental properties, many of which are situated near the picturesque Chesapeake Bay, ideal for both leisure and outdoor activities.

Travellers can expect amenities such as private swimming pools, hot tubs, outdoor seating areas, and fully equipped kitchens, making these homes great for family gatherings or groups looking to enjoy the tranquil surroundings. Some properties may also have access to nearby beaches and recreational areas, enhancing your holiday experience with opportunities for water sports and nature exploration.
Can I find long-stay holiday rentals in Charlestown?
A long-stay holiday rental in Charlestown is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any remote work holiday rentals in Charlestown?
In Charlestown, Maryland, there are approximately 27 holiday rentals that cater to remote work needs. This charming town, located along the Chesapeake Bay, offers a peaceful environment ideal for productivity. Many of these properties come equipped with reliable Wi-Fi, ensuring a smooth work experience.

Travellers can expect amenities such as spacious work areas, comfortable seating, and high-speed internet access, allowing for a seamless blend of work and relaxation. The area's proximity to nature and local attractions, including beautiful parks and waterfront views, provides an inspiring backdrop for those balancing work with leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Charlestown holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Charlestown with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Charlestown?
In Charlestown, popular holiday rental amenities include well-equipped kitchens, allowing guests to prepare their own meals. Many properties feature decks or patios, providing lovely outdoor spaces for relaxation and enjoying the surrounding scenery. Air conditioning is commonly available, ensuring comfort during warmer months. Additionally, most rentals come with coffee and tea makers, great for a warm beverage any time of day. Onsite parking is also a standard offering, making it convenient for those travelling by car.
When is the best time to visit Charlestown for a holiday rental?
The best time to visit Charlestown for a holiday rental is during the summer months, particularly in July when the town is alive with activity. This peak season, spanning from June to August, attracts travellers, eager to enjoy the warm temperatures and vibrant setting. With average highs reaching around 30°C, it's the great time for outdoor activities such as boating, fishing, and exploring the scenic waterfront.

In July, you'll find a lively community spirit, with many local events and festivals that showcase the best of Charlestown's culture and charm. The beaches are bustling, and the opportunities for sightseeing are abundant, whether you're visiting the historic sites or indulging in fresh seafood at local eateries.

For those seeking a more budget-friendly option, consider planning your visit in December. While this month falls into the low season, it brings its own unique appeal. You can enjoy a quieter experience, and perhaps even catch the festive decorations around town, making it a lovely time for a peaceful retreat.
How early should I book a Charlestown holiday rental?
Book your Charlestown holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Charlestown?
In Charlestown, Maryland, visitors can enjoy a variety of attractions that highlight the area's natural beauty and historical significance. The nearby Elk Neck State Park is a popular spot for outdoor enthusiasts, offering hiking trails, picnic areas, and stunning views of the Chesapeake Bay. This park is ideal for those who enjoy birdwatching or simply want to immerse themselves in nature.

The historic town itself features charming streets where visitors can explore local shops and eateries, providing a quaint atmosphere that reflects the town's heritage. Additionally, the proximity to the Susquehanna River allows for recreational activities such as fishing and kayaking, making it a great destination for water sports enthusiasts.
Can I change or cancel my Charlestown home rental booking on Vrbo?
To find Charlestown holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Charlestown holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More holiday ideas