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Earleville vacation rentals

We found 174 vacation rentals — enter your dates for availability

Discover a selection of 5 homes and other vacation rentals in Earleville that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation rentals have the amenities you need and want for your stay, which might include parking and a pool. No matter what 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.

Vacation rentals with weekly discounts - Earleville

Showing deals for:Dec 19 - Dec 26

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10 out of 10, Exceptional, (46 reviews)
Exceptional
(46 reviews)

Water View House in Charlestown, MD

Charlestown, MD

8% off
Price is $391
$2,735 for 7 nights
All fees included
Water View House in Charlestown, MD

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Find out more about Earleville

Find out more about Earleville

Why visit Earleville

  • Outdoor Adventures: Enjoy a variety of outdoor activities in stunning parks and marinas, perfect for nature lovers and adventure seekers.
  • Family-Friendly Atmosphere: Earleville offers numerous family-oriented activities and attractions for a memorable trip with loved ones.
  • Charming Waterfront Views: Experience the enchanting scenery of waterfront neighborhoods that provide a relaxing escape.
  • Rich Historical Vibe: Explore the area's history and culture through its quaint surroundings and local points of interest.
  • Diverse Accommodation Options: Choose from cozy cottages, charming homes, and modern apartments for a comfortable stay.

Popular types of accommodation in Earleville

Planning a getaway to Earleville? You're in for a treat. Discover a variety of popular vacation rentals, including charming houses, cozy cottages, and modern apartments. Whether you're dreaming of a beachfront escape or a peaceful holiday cottage, Earleville has something for everyone. Explore inviting suites in nearby Middletown or Chestertown, MD, and experience the comfort of a center parlor room. Your perfect stay awaits.

  • Houses: The top choice for travelers heading to Earleville, offering spacious and comfortable accommodations ideal for families or groups.
  • Cottages: A delightful option for those seeking a cozy and charming retreat amidst nature.
  • Apartments: Perfect for couples or solo travelers, these rentals provide convenience and a home-like atmosphere.
  • Cabins: A popular pick among nature enthusiasts, offering a rustic escape with modern amenities.
  • Condos: Great for those wanting a blend of luxury and convenience, often located near local attractions.**

Top attractions in and around Earleville

Earleville, Maryland, is perfect for outdoor enthusiasts and adventure seekers, offering stunning scenery and a family-friendly atmosphere. Explore local points of interest such as marinas, urban parks, and beautiful parks that provide opportunities for beach experiences and outdoor activities. Whether traveling with family or friends, you'll find plenty to enjoy in and around this charming town.

  • Bohemia Vista Marina: Experience the vibrant beach vibes at Bohemia Vista Marina. Located 5 miles from Earleville, this marina offers adventure with water activities, fishing, and beautiful views of the Bohemia River, perfect for outdoor enthusiasts.
  • Elk Neck State Park: Just 5 miles from Earleville, Elk Neck State Park is a haven for nature lovers. Explore scenic trails, enjoy stunning waterfront views, and partake in a variety of outdoor adventures like hiking and birdwatching.
  • Mount Harmon Plantation: Situated within Earleville, Mount Harmon Plantation immerses you in local history and culture. Tour the beautifully restored estate, stroll through the gardens, and learn about the rich heritage of the region.

Things to do recommended for couples

For a romantic getaway in Earleville, explore the charming Crow Farm and Vineyard, only 7 miles away, or indulge in the enchanting atmosphere at Mount Felix Vineyard & Winery and Tilmon's Island Winery, both 15 miles from town. Enjoy wine tastings and beautiful scenery together.

Things to do recommended for families

Families visiting Earleville can catch an exciting game at Ripken Stadium, enjoy outdoor fun at Glasgow Park, or play tennis at Elkton Indoor Tennis. Each location offers a unique experience, perfect for creating lasting memories together.

Things to do recommended for groups

Enjoy a round of golf at Bulle Rock Golf Course, explore local goods at the Dutch Country Farmers Market, and catch a show at the Milburn Stone Theater for a mix of sports, shopping, and culture—all within a short drive from Earleville.

*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 Earleville

If you’re traveling with friends, family, or pets, or if you’re planning an extended stay, be sure to apply the appropriate filters to match your needs. Here are some helpful tips for booking on Vrbo.

  • Traveling to Earleville with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Earleville with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with finding age-appropriate amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Earleville: For many families, a trip wouldn’t feel complete without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly homes offer feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Earleville: If you're in search of vacation rentals that offer great discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking spot, a well-equipped kitchen, or a private pool in your search for the ideal getaway.

Where to stay in and around Earleville

Earleville, Maryland, is a hidden gem perfect for outdoor enthusiasts and those seeking a relaxing getaway. Surrounded by enchanting views and waterfront neighborhoods, this charming area offers a rich historical vibe and family-friendly activities. Explore nearby towns for delightful excursions, bask in sunny weather, and enjoy the peaceful residential atmosphere. Whether you're on an adventure or unwinding, Earleville promises a memorable experience for every traveler.

  • Aberdeen: Located 15 miles from Earleville, Aberdeen is a vibrant city known for its blend of sports, business, and family-friendly experiences. Visitors can explore shopping centers and malls, making it a great spot for those looking to indulge in retail therapy. The city features notable landmarks like sports facilities and stadiums, where you can catch a live game or attend various events. With a welcoming atmosphere and an array of educational opportunities, Aberdeen offers a fulfilling travel experience for families and sports enthusiasts alike.
  • White Crystal Beach: Nestled close to Earleville, White Crystal Beach is a charming village perfect for outdoor lovers and those seeking a romantic getaway. This picturesque destination features a lovely boardwalk and recreational areas that invite visitors to soak up the sun and enjoy beach activities. The local beach and nearby national state park provide opportunities for hiking, wildlife watching, and family fun. Whether you're looking to relax on the sand or explore nature, White Crystal Beach is a delightful escape for all.
  • Cecilton: Just 3 miles from Earleville, Cecilton is an adventurous city that captivates visitors with its scenic beauty and outdoor activities. Known for its recreational areas and motor racing, this destination is ideal for thrill-seekers and nature enthusiasts. Cecilton’s proximity to national parks and beaches allows for a myriad of outdoor adventures, from hiking to picnicking. With stunning views and engaging activities, Cecilton offers a refreshing experience for those looking to explore the great outdoors.

Best time to go to Earleville

If you're planning a trip to Earleville, 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 February and November to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January32.9°F (0.5°C)Light RainMostly SunnyAverageSlightly Low
February35.6°F (2.0°C)Light RainMostly SunnySlightly LowSlightly Low
March43.0°F (6.1°C)Light RainMostly SunnyAverageSlightly Low
April53.4°F (11.9°C)Light RainMostly SunnyAverageAverage
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
November46.2°F (7.9°C)Light RainMostly SunnySlightly LowAverage
December38.7°F (3.7°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Are you hoping to cut costs on your upcoming journey? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to take advantage of substantial savings. To discover a Vrbo property that meets your financial needs, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect fit for your trip.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire booking. Being the planner truly has its benefits. When you join our travel rewards program, One Key, you’ll gain access to exclusive member discounts and earn OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers an easy and organized way to plan your travels. You can start new trips, resume planning from where you paused, or review and arrange your existing plans. You’ll see your saved or booked properties neatly organized into categories like Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply head over to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The historic city of Earleville awaits you

The area's history and museums are just a few of the reasons to vacation in Earleville. This city has something for everyone. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Earleville

Do you want to discover attractions to see in the city? Venture out of your vacation home and experience everything that makes Earleville a fun place to get away. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Back Creek Golf Club (10.3 mi / 16.5 km)
  • Bulle Rock Golf Course (14.4 mi / 23.2 km)
  • Tilmon's Island Winery (15.2 mi / 24.5 km)
  • Frightland (16.3 mi / 26.3 km)
  • Dove Valley Winery (19 mi / 30.5 km)
  • Crow Farm and Vineyard (6.7 mi / 10.7 km)

Exploring the natural landscape of Earleville

Whether you're looking for fun outdoor activities or just want to take in the scenery, Earleville is a great place to spend some time outside. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • North East Beach Area (6.6 mi / 10.6 km)
  • Betterton Beach (8.4 mi / 13.5 km)
  • Millard Tydings Memorial Park (12.6 mi / 20.3 km)
  • Garrett Island Beach (13.6 mi / 21.9 km)
  • Belcamp Beach (17.3 mi / 27.8 km)
  • Earleville Wildlife Management Area (1.8 mi / 2.9 km)

Traveling to and around Earleville

The nearest airport is in Baltimore, MD (MTN-Martin State), located 27.6 mi (44.4 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Easton, MD (ESN-Easton - Newnam), which is 42.5 mi (68.4 km) away.

Frequently asked questions

What is the best area to stay in Earleville when booking a vacation rental?
When considering a vacation rental in Earleville, Maryland, a popular area to stay is near the waterfront along the Sassafras River. This picturesque locale offers a tranquil setting, great for those looking to unwind while enjoying the scenic beauty of the river. The proximity to outdoor activities is a major draw; you can easily access kayaking, fishing, and hiking opportunities.

In addition to its natural allure, staying near the Sassafras River puts you close to attractions like the Sassafras Natural Resources Management Area, which offers beautiful trails and a chance to immerse yourself in local wildlife. Another point of interest is the nearby historic town of Chesapeake City, known for its charming shops and lovely views of the C&D Canal.

The waterfront area typically has a variety of vacation rental properties, allowing visitors to choose from cozy cabins to spacious homes, making it a versatile choice for families or couples.
How much does it cost to rent a vacation home in Earleville?
Prices for vacation rentals in Earleville 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 Earleville 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 Earleville vacation house rentals?
You can find great discounts on house rentals in Earleville 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.
Where are the best areas for renting a beach house in Earleville?
For renting a beach house in Earleville, Maryland, travelers should focus on the nearby Chesapeake Bay area, particularly around North East and Elkton. The waterfront properties along the bay often come with breathtaking views, private docks, and easy access to the water, making them ideal for boating and fishing enthusiasts. Many rentals in this region feature spacious outdoor decks, fire pits, and picnic areas, superb for enjoying warm evenings by the shore.

The North East River area offers a variety of vacation homes that provide a blend of comfort and convenience, with amenities such as modern kitchens, air conditioning, and washer/dryer facilities. These accommodations are typically within a short drive of local attractions like the North East Town Park, which provides recreational opportunities including walking trails and picnic spots.

Additionally, visitors can explore nearby parks and nature reserves, such as Elk Neck State Park, which is a great place for hiking and enjoying the natural beauty of the region. Rentals here may include features like outdoor grills, access to hiking trails, and sometimes even kayaks or bicycles for exploring the local area.
What is the most popular type of vacation rental accomodation in Earleville?
In Earleville, vacation houses are the most common type of rental accommodation, with several options available throughout the area. These homes typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable stay. Many also include outdoor decks or patios, providing lovely views of the surrounding nature and opportunities for relaxation. Additionally, there are several cottages and villas, which offer a quaint, charming atmosphere, often set in picturesque locations near the shoreline.
Are there any family house rentals in Earleville?
In Earleville, Maryland, there are several family-friendly house rentals available, making it a suitable spot for family gatherings. The area features properties with spacious living areas, fully equipped kitchens great for preparing family meals, and outdoor spaces where children can play and explore. Many of these homes also offer amenities such as Wi-Fi and air conditioning to ensure a comfortable stay.

For family-friendly activities, visitors can enjoy the nearby Sassafras River, ideal for kayaking and fishing, or explore the natural beauty of the surrounding parks.
Can I rent a vacation home with a pool or hot tub in Earleville?
In Earleville, Maryland, there are several vacation homes available for rent that come with pools or hot tubs, making it a great option for those seeking relaxation and leisure during their stay. The area, which is known for its scenic views and proximity to the Chesapeake Bay, offers rentals that often feature private pools, spacious outdoor areas, and hot tubs, superb for unwinding after a day of exploring. Many of these homes also include amenities such as fully equipped kitchens, comfortable living spaces, and outdoor dining areas, allowing for an enjoyable family experience.
Can I find long-stay vacation rentals in Earleville?
A long-stay vacation rental in Earleville 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 pet-friendly house rentals in Earleville?
In Earleville, travelers can find several pet-friendly house rentals that cater to a variety of needs. Many of these properties offer amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces superb for both guests and their furry companions. The area is surrounded by beautiful landscapes, providing a serene setting for relaxation and outdoor activities.

Additionally, the nearby Sassafras River offers opportunities for kayaking and fishing, making it an appealing choice for nature lovers. The region is also close to several parks where pets are welcome, ensuring that visitors have ample options for walks and outdoor leisure activities.
Are there any remote work vacation rentals in Earleville?
In Earleville, Maryland, there are several vacation rentals that cater to remote work needs. Many properties in this area come equipped with essential amenities such as Wi-Fi, dedicated workspaces including desks and chairs, allowing for productivity during your stay. The serene environment provides a superb backdrop for focused work sessions, while still being close to local attractions.

Travelers can enjoy the natural beauty of the nearby Chesapeake Bay, with opportunities for outdoor activities like hiking and fishing. The peaceful surroundings of Earleville make it an ideal spot for those looking to balance work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Earleville vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Earleville 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 Earleville?
In Earleville, popular vacation rental amenities include WiFi, kitchens equipped with essential appliances like blenders and coffee/tea makers, and outdoor patios for enjoying the serene surroundings. These features make rentals ideal for travelers seeking comfort and convenience, allowing them to prepare their meals and relax outdoors after a day of exploring the charming countryside of Maryland.
When is the best time to visit Earleville for a vacation rental?
August is the most popular month to visit Earleville, as it falls within the peak season from June to August. During this vibrant time, travelers flock to the area to enjoy the warm weather and partake in a variety of outdoor activities. With temperatures typically ranging from the mid-70s to the low 90s Fahrenheit, August offers a comfortable climate for exploring the scenic beauty of the Chesapeake Bay region, making it ideal for boating, fishing, and hiking.

The summer months also bring a bustling atmosphere, with plenty of events and festivals that highlight local culture and cuisine. This lively environment is great for families and groups seeking to create unforgettable memories, whether you're relaxing by the water or discovering hidden gems in the surrounding area.

For those mindful of their budgets, December presents a wonderful opportunity to visit Earleville at a lower cost. It's cooler, with temperatures averaging in the upper 30s to low 50s Fahrenheit, the serene winter landscape offers a peaceful retreat. You can enjoy cozy indoor activities, explore local shops, and savor the charm of the town without the crowds.

Ultimately, the best time to book a vacation rental in Earleville depends on your preferences.
How early should I book a Earleville vacation rental?
Book your Earleville 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 Earleville?
In Earleville, Maryland, visitors can enjoy attractions that showcase the area's natural beauty and history. The nearby Sassafras River offers opportunities for boating, fishing, and picturesque views. The town is also close to the Chesapeake and Delaware Canal, which features scenic trails for walking and biking. For those interested in history, the region has several historical sites, including old churches and landmarks that reflect its historic past.
Can I change or cancel my Earleville home rental booking on Vrbo?
To find Earleville 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Earleville 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.

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