Charlestown vacation rentals

We found 147 vacation rentals — enter your dates for availability

Discover a selection of 7 homes and other vacation rentals in Charlestown that are perfect for your trip. Vacation homes provide the best amenities for your stay with friends, family, or just your pet, like WiFi and parking. At the end of the day, you'll find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Charlestown

Showing deals for:Aug 7 - Aug 14

Image gallery for Vintage Waterfront Cottage with Stunning Sunsets

Beach
10 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

Vintage Waterfront Cottage with Stunning Sunsets

North East

9% off
Price is $445
$3,113 for 7 nights
All fees included
Vintage Waterfront Cottage with Stunning Sunsets

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Find out more about Charlestown

Why visit Charlestown

  • Beautiful Beaches: Enjoy the scenic beauty of Charlestown Beach, perfect for relaxation and family fun.
  • Outdoor Activities: Explore urban parks and marinas, offering a variety of recreational opportunities.
  • Charming Accommodations: Choose from private vacation homes, cozy cottages, and comfortable apartments for a budget-friendly stay.
  • Rich Local Culture: Immerse yourself in the town’s history and friendly atmosphere, perfect for creating lasting memories.
  • Family-Friendly Environment: Discover nearby neighborhoods that cater to families, making it ideal for all ages.

Popular types of accommodation in Charlestown

If you're exploring vacation rentals in Charlestown, you're in for a treat. The most popular types of accommodations include houses, charming cottages, and comfortable apartments. Whether you're seeking the best hotels in Charlestown or an ideal house rental for your getaway, we have a variety of options to suit your needs. Enjoy a stay that combines transparency, savings, and reassurance as you discover the perfect place to unwind.

  • Houses: A favorite among travelers, these homes offer a spacious and comfortable setting for families, friends, or couples.
  • Cottages: These quaint and charming retreats provide a cozy atmosphere, perfect for a relaxing getaway.
  • Apartments: Ideal for those seeking convenience and a home-like feel, apartments are a popular choice for visitors.
  • Cabins: Offering a rustic escape, cabins are perfect for nature enthusiasts looking for adventure.
  • Caravan Parks: For a more communal experience, caravan parks offer a fun and budget-friendly option.**

Top attractions near Charlestown

Charlestown, Maryland, is perfect for outdoor enthusiasts and beach lovers alike. Visitors can explore a variety of attractions, including urban parks, marinas, and museums, making it an ideal destination for families and those seeking a vibrant city experience. With its scenic views and recreational opportunities, Charlestown offers a delightful getaway for travelers looking to enjoy nature and local culture.

  • Havre de Grace Promenade: A beautiful esplanade offering stunning views of the water, perfect for a leisurely stroll with family or a romantic walk. Enjoy outdoor activities and the vibrant atmosphere of this scenic spot located 6 miles from Charlestown.
  • Concord Point Lighthouse: This historic lighthouse, also situated 6 miles away, showcases rich maritime culture and offers a glimpse into the area's seafaring past, making it a must-visit for history enthusiasts.
  • Conowingo Dam: Located 12 miles away, this impressive dam features breathtaking scenery and opportunities for wildlife observation, especially birdwatching, in a serene natural setting.

Things to do recommended for couples

Charlestown, Maryland, offers a charming escape for couples. Enjoy a leisurely stroll along the waterfront, savor a candlelit dinner at a cozy local restaurant, or explore the scenic beauty of the nearby parks together. Don't miss the breathtaking sunset views over the Chesapeake Bay.

Things to do recommended for families

Families visiting Charlestown can enjoy a fun-filled day at the nearby Elk Neck State Park, where kids can hike scenic trails and explore the beach. Additionally, the charming local shops offer unique finds, making it a perfect spot for family bonding and exploration.

Things to do recommended for groups

Explore the scenic views along the Susquehanna River, enjoy a thrilling day of kayaking or paddleboarding, and savor fresh seafood at local eateries. Don’t miss the chance to visit nearby parks for hiking and picnicking with your group.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Charlestown

If you're traveling with a group, family, or pets, or if you're planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Charlestown with a group: Think about how many bedrooms you'll require, as well as any amenities like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these features and more on Vrbo.
  • Traveling to Charlestown with young kids: Traveling with young children can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it's wise to think about how close you are to attractions that are enjoyable for families.
  • Taking your pets with you to Charlestown: For many families, a vacation wouldn’t be the same without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that all members of your family feel at home.
  • Planning for a long term stay visiting Charlestown: If you're in search of vacation rentals that offer discounts for stays of a month or longer, you've come to the right spot. By using the right filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding options like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay near Charlestown

Charlestown, Maryland, is a charming coastal town perfect for outdoor and beach vacations. Enjoy the scenic beauty of Charlestown Beach and explore nearby neighborhoods that offer a family-friendly atmosphere. With convenient vacation rentals, you'll find budget-friendly options to suit your needs. Whether you're seeking relaxation or adventure, this picturesque region provides a delightful blend of history, friendly locals, and stunning landscapes to create unforgettable memories.

  • Newark: Located 14 miles from Charlestown, Newark is a vibrant city known for its family-friendly atmosphere and cultural experiences. Visitors can enjoy a mix of education and entertainment at the local historic college university, which adds to the town's charm. Shopping enthusiasts will appreciate the nearby shopping centers and malls, providing ample options for retail therapy. Newark also boasts beautiful urban parks, perfect for a leisurely stroll or a family picnic, making it an excellent destination for those seeking both culture and recreation.
  • Perryville: Just 5 miles from Charlestown, Perryville is an exciting city that caters to families and outdoor enthusiasts alike. This city offers a range of entertainment options, including a thrilling water park and an amusement park, guaranteeing fun for all ages. The lively boardwalk area invites visitors to enjoy waterfront activities and delicious dining options. With its proximity to a theme park and scenic bay views, Perryville promises a delightful experience filled with adventure and enjoyment for the whole family.
  • Havre De Grace: Situated 6 miles from Charlestown, Havre De Grace is a picturesque city known for its stunning scenery and outdoor activities. This charming destination offers a variety of recreational areas, golf courses, and educational opportunities, making it perfect for nature lovers and adventure seekers. Visitors can relax on the local beaches or explore the nearby national state park, which showcases the area's natural beauty. With its inviting atmosphere and scenic bay views, Havre De Grace is a must-visit for those looking to unwind and appreciate the great outdoors.

Best time to go to Charlestown

If you're planning a trip to Charlestown, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January32.9°F (0.5°C)Light RainMostly SunnySlightly LowAverage
February35.6°F (2.0°C)Light RainMostly SunnyAverageSlightly Low
March43.0°F (6.1°C)Light RainMostly SunnyAverageSlightly Low
April53.4°F (11.9°C)Light RainMostly SunnyAverageSlightly Low
May63.1°F (17.3°C)Light RainMostly SunnyAverageAverage
June71.6°F (22.0°C)Light RainMostly SunnySlightly HighSlightly High
July77.0°F (25.0°C)Light RainMostly SunnySlightly HighSlightly High
August75.0°F (23.9°C)Light RainMostly SunnySlightly HighSlightly High
September68.7°F (20.4°C)Light RainMostly SunnyAverageAverage
October58.1°F (14.5°C)Light RainMostly SunnyAverageAverage
November46.0°F (7.8°C)Light RainMostly SunnySlightly LowAverage
December39.0°F (3.9°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides a convenient platform for you to plan new trips, revisit your existing plans, or manage your bookings. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Choose a vacation rental for your Charlestown getaway

Learn about the unique charm of Charlestown with a stay in a private vacation home. This city has something for everyone. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation 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

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

  • 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 adventure or just want to take in the scenery, Charlestown is a great place to get outside. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • 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)

Transportation to and around Charlestown

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

Frequently asked questions

What is the best area to stay in Charlestown, Maryland, United States of America when booking a vacation rental?
When considering a vacation rental in Charlestown, Maryland, the area around the waterfront is a fantastic choice. This charming neighborhood offers stunning views of the Chesapeake Bay and provides easy access to outdoor activities such as fishing and boating. A popular attraction nearby is the picturesque North East River, great for kayaking or enjoying a peaceful day by the water.

Another appealing aspect of this area is its proximity to the historical sites and natural beauty of Elk Neck State Park. This park features beautiful hiking trails and scenic vistas, making it a wonderful spot for nature lovers. While the number of properties may vary, the waterfront area typically has a range of rentals, from cozy cottages to spacious homes, ensuring a comfortable stay for visitors.
How much does it cost to rent a vacation home in Charlestown?
Prices for vacation 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 vacation 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 vacation rental accomodation in Charlestown?
In Charlestown, vacation houses are the most popular type of rental, with several available throughout the area. These spacious homes typically feature multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or decks, making them ideal for families or groups looking to enjoy the serene surroundings near the Chesapeake Bay. Cottages are also a common choice, offering a cozy atmosphere with charming decor, often located close to local parks and waterfront areas. Additionally, several apartments can be found, providing a more compact living option for travelers seeking convenience and comfort.
Are there any family house rentals in Charlestown?
In Charlestown, Maryland, there are several family-friendly vacation rentals available. This charming waterfront town offers a variety of spacious homes great for families looking to enjoy a relaxing getaway. Many of these properties feature amenities such as fully equipped kitchens, large living areas for family gatherings, and outdoor spaces where kids can play.

Visitors can explore nearby attractions, including the scenic views along the Chesapeake Bay and the recreational opportunities at nearby parks. Whether it's a day at the beach or a picnic by the water, families will find plenty to do in this welcoming locale.
Can I rent a vacation home with a pool or hot tub in Charlestown?
In Charlestown, Maryland, there are several vacation homes available for rent that feature pools and hot tubs. This charming town, located along the Chesapeake Bay, offers a variety of properties, particularly in areas close to the water, where guests can enjoy both relaxation and scenic views. Many of these rentals come equipped with private pools or hot tubs, outdoor decks for lounging, and fully equipped kitchens, superb for families or groups looking to unwind after a day of exploration.
Can I find long-stay vacation rentals in Charlestown?
A long-stay vacation rental in Charlestown is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any remote work vacation rentals in Charlestown?
In Charlestown, Maryland, there are several vacation rentals that cater to remote work needs. Travelers can expect properties equipped with high-speed internet, suitable for video conferencing and other online work tasks. Many rentals offer free Wi-Fi in both common areas and individual units, ensuring connectivity throughout your stay.

The town is located along the scenic Chesapeake Bay, providing not only a serene environment for work but also opportunities for outdoor activities during breaks. Nearby attractions include the Elk Neck State Park, which features beautiful hiking trails and waterfront views, great for relaxation after a productive day. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Charlestown vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Charlestown with parking available—perfect for families or travelers 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 vacation rental amenities cater to a comfortable and convenient stay. Travelers can expect most rentals to include a fully equipped kitchen, allowing for home-cooked meals and family gatherings. Many properties feature a deck or patio, superb for enjoying the scenic views and fresh air. Air conditioning is commonly available to ensure comfort during warmer months. Additionally, rentals often include a coffee and tea maker for those early mornings or leisurely afternoons, and onsite parking is typically provided for guests with vehicles.
When is the best time to visit Charlestown for a vacation rental?
The best time to visit Charlestown for a vacation rental is during the vibrant summer months from June to August, with July standing out as the most popular month. This peak season attracts travelers seeking sun-soaked days, superb for enjoying the picturesque waterfront and engaging in various outdoor activities. The warm climate, typically ranging from the mid-70s to mid-90s Fahrenheit, makes it ideal for swimming, boating, and exploring local parks.

During these peak months, visitors can experience firsthand the lively option filled with festivals and community events, offering a taste of the local culture. The charm of Charlestown shines brightest in summer, as families and friends gather to enjoy the scenic beauty and recreational opportunities.

For those looking for a more budget-friendly option, consider visiting in December. While this month is quieter, it provides a unique chance to experience the holiday spirit in a serene setting. You can enjoy coastal walks and the tranquility of the area without the hustle and bustle of high tourist traffic.

Ultimately, your choice will depend on whether you prefer the energetic vibe of summer or the peacefulness of winter.
How early should I book a Charlestown vacation rental?
Book your Charlestown vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Charlestown, Maryland, United States of America?
In Charlestown, Maryland, visitors can enjoy a blend of natural beauty and historical charm. The town is situated along the scenic Chesapeake Bay, making it a great spot for water-related activities such as fishing, boating, and kayaking. The nearby North East River offers beautiful views and opportunities for outdoor recreation.

Charlestown is close to the historic Fort Howard Park, which provides a glimpse into the area's military past while offering picnic areas and waterfront access. Additionally, the charming small-town atmosphere can be experienced by exploring local shops and eateries that line the streets.

For those interested in nature, the nearby Elk Neck State Park features hiking trails, camping facilities, and stunning views of the Bay, making it a superb day-trip destination for outdoor enthusiasts.
Can I change or cancel my Charlestown home rental booking on Vrbo?
To find Charlestown vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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.

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