Chesapeake City vacation rentals

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Discover a selection of 9 homes and other vacation rentals in Chesapeake City that are perfect for your trip. Vacation homes provide the amenities you need and want for you and your friends, family, or even pets, such as parking and a washer and dryer. At the end of the day, you'll be able to choose a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Chesapeake City

Showing deals for:Dec 5 - Dec 12

Image gallery for Water View House in Charlestown, MD

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10 out of 10 rating
Exceptional
(44 reviews)

Water View House in Charlestown, MD

Charlestown, MD

8% off
Price is $387
$2,709 for 7 nights
All fees included
Water View House in Charlestown, MD

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Find out more about Chesapeake City

Find out more about Chesapeake City

Why visit Chesapeake City

  • Scenic waterfront: Enjoy breathtaking views of the Chesapeake Bay, perfect for relaxation and family activities.
  • Outdoor recreation: Explore urban parks, marinas, and nearby state parks for adventure and nature experiences.
  • Charming local shops: Stroll through picturesque towns filled with unique boutiques and waterfront relaxation spots.
  • Welcoming atmosphere: Experience the friendly vibe and historical charm that make Chesapeake City a memorable destination.
  • Diverse accommodations: Find a range of vacation rentals, from cozy homes to quaint cottages, suited for any group size.

Popular types of accommodation in Chesapeake City

Discover the charm of Chesapeake City with our selection of vacation rentals tailored to meet your needs. Whether you’re looking for a cozy private vacation home, a quaint cottage, or a comfortable apartment, we’ve got you covered. Explore our Chesapeake City house rentals and vacation homes to find the perfect base for your getaway. No matter your group size or activities planned, there’s an ideal rental waiting for you in this picturesque destination.

  • Houses: The top choice among travelers, these homes offer spacious accommodations perfect for families or groups seeking a home-like atmosphere.
  • Cottages: These quaint and charming retreats provide a cozy ambiance, ideal for a peaceful getaway.
  • Apartments: A convenient option for visitors, apartments offer modern amenities and easy access to local attractions.
  • Cabins: Nestled in nature, cabins provide a rustic escape for those looking to unwind in a serene environment.
  • Condos: Offering a mix of comfort and convenience, condos are a great choice for travelers seeking a home away from home.**

Top attractions in and around Chesapeake City

Chesapeake City, Maryland, is perfect for outdoor and family vacations, offering beautiful scenery and a variety of attractions. Visitors can explore urban parks, marinas, and nearby national state parks, making it ideal for those seeking both adventure and a city experience. Don't miss the stunning views of the Chesapeake Bay, which adds to the area's charm and appeal for travelers looking to enjoy nature and family-friendly activities.

  • University of Delaware: This historic university is known for its vibrant campus culture and beautiful architecture. Just 11 miles from Chesapeake City, you can explore its rich academic history and enjoy the scenic surroundings.
  • Bohemia Vista Marina: Located within Chesapeake City, this marina offers thrilling outdoor adventures, from boating to fishing. Experience the relaxing beach vibes while enjoying the stunning views of the water.
  • C and D Canal Museum: Situated in Chesapeake City, this museum showcases the region's maritime history and culture. Discover fascinating exhibits that highlight the significance of the C and D Canal.

Things to do recommended for couples

For a romantic getaway in Chesapeake City, explore nearby wineries like Dove Valley Winery and Crow Farm and Vineyard, both 16 miles away, or visit Paradocx Vineyard, 17 miles away. Enjoy the enchanting atmosphere, perfect for couples seeking love and entertainment.

Things to do recommended for families

In Chesapeake City, families can unwind at Glasgow Park, just 7 miles away, or enjoy indoor fun at Elkton Indoor Tennis, 5 miles away. For a thrilling day, head to Fred Rust Ice Arena, 10 miles away, for ice skating and adventure.

Things to do recommended for groups

Experience excitement at Mansion House Paintball for an adventure day, or enjoy a round at Elkton Golf and Batting Center for some friendly competition. For a leisurely afternoon, explore the Newark Shopping Center, offering shopping and entertainment for the whole 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 Chesapeake City

If you're traveling with a group, with family, bringing pets, or planning for an extended stay, it's essential to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Chesapeake City with a group: Think about how many bedrooms you’ll require, along with features like a complete kitchen or outdoor space for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Chesapeake City with young kids: Traveling with young kids can be quite an adventure. It's important to prioritize their comfort and safety, along with providing age-appropriate amenities like a private pool. Additionally, think about how close you are to family-friendly attractions to enhance your experience.
  • Taking your pets with you to Chesapeake City: For many families, a vacation wouldn’t feel complete without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chesapeake City: If you're searching for vacation rentals with special rates for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Chesapeake City

Chesapeake City, Maryland, offers a delightful blend of outdoor adventures and family-friendly activities. Explore picturesque towns and charming shore areas, where you can shop local boutiques or relax by the waterfront. The welcoming atmosphere and historical vibe make it an ideal destination for a memorable vacation. Nearby, discover beautiful properties perfect for a getaway, ensuring a serene escape surrounded by friendly locals and scenic views.

  • Newark: Located 11 miles from Chesapeake City, Newark is a vibrant city known for its family-friendly atmosphere and cultural offerings. Visitors can enjoy a range of activities, from exploring the historic college university to indulging in retail therapy at the local shopping centers and malls. Nature lovers will appreciate the nearby parks, while sports enthusiasts can catch a game at the stadium. The mix of education, shopping, and recreation makes Newark a well-rounded destination for travelers.
  • Elkton: Just 5 miles away from Chesapeake City, Elkton is perfect for those seeking outdoor adventures and family-oriented activities. The city boasts a range of recreational areas, making it ideal for picnics and outdoor fun. Visitors can explore the historic college university and enjoy the natural beauty of the national state park nearby. With a beach within reach, Elkton offers a delightful blend of culture and nature, ensuring a memorable experience for all ages.
  • Middletown: Located 7 miles from Chesapeake City, Middletown is a charming city that attracts visitors with its outdoor experiences and family-friendly environment. The city features a lively boardwalk and various shopping centers, providing ample opportunities for leisure and enjoyment. Visitors can relax at the beach, explore the local park, or visit the historic college university, making Middletown a delightful stop for those looking to soak up some sun and culture during their vacation.

Best time to go to Chesapeake City

If you're planning a trip to Chesapeake City, 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
January33.1°F (0.6°C)Light RainMostly SunnyModerately LowAverage
February35.6°F (2.0°C)Light RainMostly SunnyAverageSlightly Low
March43.0°F (6.1°C)Light RainMostly SunnyAverageSlightly Low
April53.6°F (12.0°C)Light RainMostly SunnyAverageSlightly Low
May63.1°F (17.3°C)Light RainMostly SunnyAverageAverage
June71.6°F (22.0°C)Light RainMostly SunnyModerately HighSlightly High
July77.0°F (25.0°C)Light RainMostly SunnyModerately HighSlightly High
August75.0°F (23.9°C)Light RainMostly SunnyModerately 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 SunnyModerately LowAverage
December39.0°F (3.9°C)Light RainMostly SunnyModerately LowAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider booking a longer stay, which can lead to considerable savings. To discover a Vrbo property that aligns with your budget, 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 travel needs.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire booking. It truly benefits you to take on the planning role. 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 start enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers an easy-to-use platform for planning your next adventure, picking up right where you left off, or organizing your travel plans. You can easily find the properties you've saved or booked, conveniently categorized into Potential, Upcoming, or Current Trips. To get started with Trip Boards, just visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Delight in the waterfront landscape of Chesapeake City

The area's history and museums are just a few of the reasons to vacation in Chesapeake City. Travelers appreciate the restaurants in this welcoming city. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Chesapeake City

Are you looking for top things to see and do in the area? Venture out of your cozy vacation rental and experience everything that makes Chesapeake City a one-of-a-kind vacation spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Back Creek Golf Club (3.3 mi / 5.3 km)
  • Frightland (8.5 mi / 13.7 km)
  • Dove Valley Winery (15.7 mi / 25.2 km)
  • Plumpton Park Zoo (15.9 mi / 25.5 km)
  • Bulle Rock Golf Course (17.3 mi / 27.9 km)
  • Patriots Glen Golf Club (6.3 mi / 10.1 km)

Exploring the natural features in Chesapeake City

Whether you're looking for adventure or just want to spend some time taking in the scenery, Chesapeake City is a great spot to appreciate mother nature. These are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

  • North East Beach Area (10 mi / 16.1 km)
  • Lewis Park (10.2 mi / 16.5 km)
  • University of Delaware Botanic Gardens (10.6 mi / 17.1 km)
  • Battery Park (11.9 mi / 19.1 km)
  • Chespeake & Delaware Branch Canal (12 mi / 19.2 km)
  • Kirkwood Soccer Complex (12.3 mi / 19.8 km)

Transportation to and around Chesapeake City

The nearest airport is in Baltimore, MD (MTN-Martin State), located 35.6 mi (57.3 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Baltimore Washington Intl. Airport (BWI), which is 52 mi (83.7 km) away.

Frequently asked questions

What is the best area to stay in Chesapeake City when booking a vacation rental?
When planning a vacation rental in Chesapeake City, Maryland, one of the best areas to consider is the charming waterfront district. This area is not only picturesque, with stunning views of the Chesapeake and Delaware Canal, but it also offers a convenient location near several attractions. You can explore the historic Chesapeake City Bridge, which provides a beautiful backdrop for photos, or visit the nearby C&D Canal Museum to learn about the area's rich maritime history.

Another great option is the residential neighborhoods surrounding the downtown area. Here, you will find a variety of cozy homes and cottages that cater to vacationers. This area boasts easy access to the quaint shops, local eateries, and art galleries that line the streets. Additionally, nearby parks such as the Chesapeake City Park offer scenic spots for picnics and leisurely walks along the water.

Overall, the waterfront district and surrounding neighborhoods have a healthy number of vacation rentals available, ensuring you can find something that suits your needs.
How much does it cost to rent a vacation home in Chesapeake City?
Prices for vacation rentals in Chesapeake City 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 Chesapeake City 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 Chesapeake City vacation house rentals?
You can find great discounts on house rentals in Chesapeake City 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 Chesapeake City?
For renting a beach house in Chesapeake City, Maryland, travelers should consider the serene waterfront along the Chesapeake and Delaware Canal, where many vacation rentals offer picturesque views and easy access to the water. The area surrounding the historic downtown is charming, featuring homes with amenities such as spacious decks for outdoor dining, private docks for boating, and modern kitchens equipped for family meals.

Additionally, properties near the Chesapeake City Bridge provide a unique vantage point for watching boats pass through the canal, with some rentals boasting amenities like fire pits and outdoor seating areas, superb for evening gatherings. The quaint streets of the historic district are lined with shops and restaurants, offering a blend of local cuisine and artisan goods that enhance the vacation experience.

For travelers interested in outdoor activities, the nearby Elk Neck State Park offers hiking trails and beautiful landscapes, making it a great spot for nature lovers. Rentals in this vicinity often come with amenities such as picnic areas and easy access to hiking routes. Find your rental near the beach in Chesapeake City.
What is the most popular type of vacation rental accomodation in Chesapeake City?
In Chesapeake City, vacation houses are the most popular rental option, with several available throughout the charming town. These properties typically offer spacious layouts with multiple bedrooms, fully equipped kitchens, and cozy living areas, making them ideal for families or groups. Many vacation houses also feature outdoor spaces, such as patios or decks, where guests can enjoy views of the Chesapeake Bay or relax after a day of exploring.

Apartments, cottages, cabins, and mobile homes are also prevalent, providing travelers with a variety of choices to suit different preferences and budgets. Cottages and cabins, in particular, offer a quaint and rustic charm, often set in tranquil surroundings, superb for a peaceful getaway.
Are there any family house rentals in Chesapeake City?
In Chesapeake City, visitors can find several family-friendly vacation rentals that cater to various needs. This charming waterfront town offers homes in neighborhoods that are close to the scenic Chesapeake and Delaware Canal, superb for family outings and outdoor activities. Many of these properties feature spacious living areas, full kitchens for preparing family meals, and outdoor spaces where children can play or families can gather for barbecues.

Amenities such as Wi-Fi, air conditioning, and even game rooms are often included, ensuring comfort and entertainment for all ages. The town is not far from parks and recreational areas, making it a great base for exploring local nature trails or enjoying water activities.
Can I rent a vacation home with a pool or hot tub in Chesapeake City?
In Chesapeake City, there are several vacation homes available for rent that feature pools and hot tubs, providing great options for relaxation and enjoyment. The charming waterfront town offers a serene atmosphere, with many properties located near the Chesapeake and Delaware Canal, allowing for picturesque views and easy access to outdoor activities. Travelers can expect amenities such as private swimming pools, hot tubs for unwinding after a day of exploration, spacious outdoor decks, and fully equipped kitchens superb for family meals.
Can I find long-stay vacation rentals in Chesapeake City?
A long-stay vacation rental in Chesapeake City 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 Chesapeake City?
In Chesapeake City, travelers can find several pet-friendly house rentals that cater to those looking to enjoy a charming waterfront experience. Many of these homes come equipped with modern amenities such as fully stocked kitchens, outdoor grills, and spacious living areas, making them ideal for families or groups. Some properties also feature private decks or patios, providing picturesque views of the Chesapeake and Delaware Canal, great for relaxing with pets.

The quaint town itself is known for its historic charm and scenic beauty, offering various parks and green spaces where pets can enjoy walks. Nearby, the Chesapeake City Park provides ample room for pets to roam and play, while the waterfront area is ideal for leisurely strolls.
Are there any remote work vacation rentals in Chesapeake City?
In Chesapeake City, there are several remote work vacation rentals available, specifically around 13 options that cater to those needing a productive environment. Many of these properties are situated near the charming waterfront, providing a serene backdrop for work and relaxation. Travelers can expect amenities tailored for remote work, including high-speed Wi-Fi, dedicated office spaces, desks, and comfortable chairs, ensuring a conducive atmosphere for getting tasks completed.

The town itself offers a quaint atmosphere with historic buildings and scenic views of the Chesapeake and Delaware Canal. Nearby, visitors can enjoy local restaurants and small shops, adding to the convenience of the location. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chesapeake City vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Chesapeake City 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 Chesapeake City?
In Chesapeake City, popular vacation rental amenities include WiFi, allowing guests to stay connected during their stay. Many rentals feature fully equipped kitchens, which provide the convenience of preparing meals at home. A coffee and tea maker is commonly found in these properties, great for those who enjoy a morning brew. Additionally, outdoor spaces such as decks or patios are prevalent, offering a relaxing area to unwind while enjoying the scenic views of the Chesapeake and Delaware Canal.
When is the best time to visit Chesapeake City for a vacation rental?
July is the most popular time to visit Chesapeake City, as it falls within the peak season from June to August. During these summer months, travelers flock to this charming waterfront town to enjoy a variety of outdoor activities, including boating, fishing, and exploring the scenic C&D Canal. The warm weather, with temperatures typically ranging from the mid-70s to mid-80s Fahrenheit, creates a friendly space for leisurely strolls along the historic waterfront and dining al fresco at local eateries.

If you prefer a more relaxed experience, consider visiting in November when the crowds have diminished, yet the beauty of Chesapeake City remains. This shoulder month offers pleasant weather for exploring the quaint shops and enjoying the peaceful surroundings without the hustle and bustle of summer tourists.

Regardless of when you decide to visit, Chesapeake City promises a delightful blend of history, charm, and natural beauty.
How early should I book a Chesapeake City vacation rental?
Book your Chesapeake City 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 Chesapeake City?
In Chesapeake City, visitors can enjoy a charming small-town atmosphere with several attractions. The historic downtown area features beautifully preserved 19th-century buildings, quaint shops, and delightful eateries. The C&D Canal Museum offers insights into the area's history and its significance in the region's maritime activities. The waterfront park along the canal is great for leisurely strolls and picnics, providing scenic views of the waterway. Nearby, the Chesapeake City Bridge offers picturesque vistas and is a great spot for photography.
Can I change or cancel my Chesapeake City home rental booking on Vrbo?
To find Chesapeake City 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 Chesapeake City 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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