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Chesapeake Beach vacation rentals

We found 842 vacation rentals — enter your dates for availability

Discover a selection of 7 homes and other vacation rentals in Chesapeake Beach that are perfect for your trip. Whether you're staying in a vacation rental with family, friends, or just your furry companion, you'll find the amenities you need and want, which might include a hot tub and a washer and dryer. You're sure to find a rental that has what everyone needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Chesapeake Beach

Showing deals for:Jan 9 - Jan 16

Image gallery for Unbelievable beach views for 6

You can't get much closer to the Chesapeake Bay than this 2-bed/1-bath gem that sleeps 6!
10 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)

Unbelievable beach views for 6

North Beach, MD

10% off
Price is CA $306
CA $2,698 total
includes taxes & fees
Unbelievable beach views for 6

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Find out more about Chesapeake Beach

Find out more about Chesapeake Beach

Why visit Chesapeake Beach

  • Beautiful Beaches: Enjoy the pristine sandy shores and stunning views along Chesapeake Bay, perfect for relaxation.
  • Outdoor Activities: Engage in various activities like hiking, tent camping, and eco-friendly excursions to connect with nature.
  • Charming Accommodations: Choose from a selection of cozy cottages, inviting apartments, and private vacation homes for a comfortable stay.
  • Family-Friendly Atmosphere: Experience a welcoming environment ideal for families and couples seeking quality time together.
  • Local Attractions: Discover unique local spots and vibrant community events that enrich your visit to Chesapeake Beach.

Popular types of accommodation in Chesapeake Beach

If you're exploring vacation rentals in Chesapeake Beach, you're in for a treat. This charming destination offers an array of accommodations, including houses, cozy cottages, and inviting apartments. Whether you're seeking Chesapeake Beach cabin rentals or looking to unwind in a quaint cottage, we have the perfect options for you. Enjoy transparency and reassurance as you find your ideal getaway.

  • Houses: The top choice for visitors to Chesapeake Beach, these homes offer spacious accommodations ideal for families, friends, or couples seeking a comfortable stay.
  • Cottages: A delightful option for a quaint and cozy getaway, cottages are perfect for those who appreciate charm and a homey feel.
  • Apartments: A convenient choice for solo travellers or couples, apartments provide modern amenities and easy access to local attractions.
  • Condos: These stylish units combine luxury with comfort, making them a popular pick for those wanting a resort-style experience.
  • Cabins: Ideal for nature enthusiasts, cabins offer a rustic escape surrounded by the beauty of the outdoors.**

Top attractions in Chesapeake Beach

Chesapeake Beach, Maryland, is perfect for outdoor enthusiasts and families seeking a romantic getaway. Visitors can explore urban parks, pristine beaches, and the scenic Chesapeake Bay. Excursions and beach breaks are popular activities, alongside tent camping for those wanting to connect with nature. With a focus on eco-friendly experiences, Chesapeake Beach offers a variety of attractions that cater to all types of travellers looking to enjoy the great outdoors.

  • Breezy Point Beach: Enjoy a relaxed atmosphere at Breezy Point Beach, where you can soak up the sun on the sandy shores, take leisurely strolls, and indulge in beach vibes perfect for unwinding or family fun.
  • Rod n Reel Charter Fishing: Experience the thrill of outdoor adventure with Rod n Reel Charter Fishing. Enjoy a day on the water, casting lines and reeling in the catch of the day amidst a vibrant marina setting.
  • Chesapeake Beach Railway Museum: Immerse yourself in local culture at the Chesapeake Beach Railway Museum. Discover the rich history of the area’s railway system through engaging exhibits that highlight its significance to the community.

Things to do recommended for couples

Looking for a romantic getaway in Chesapeake Beach? Visit St. Michaels Winery for a delightful tasting experience, enjoy a fun round of mini-golf at R&J's PlayPark, or indulge in luxury at the Old South Country Club. Each spot offers unique vibes perfect for couples.

Things to do recommended for families

Your family will have a blast at the Chesapeake Beach Water Park, enjoying thrilling slides and splashes. For a serene outing, visit Allen Pond Park, perfect for relaxation. Catch a game at Prince George's Stadium for a true sports experience, all within a short drive from Chesapeake Beach.

Things to do recommended for groups

Groups visiting Chesapeake Beach can enjoy a round of golf at Renditions Golf Club, shop at the Bay Bridge Market Place Shopping Center for local goods, and explore the Wild Bird Center for a unique experience in nature. Each activity offers a delightful taste of the area.

*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 Beach

When planning your trip—whether you're traveling with a group, as a family, bringing your pets, or seeking extended stays—it's important to prioritize your preferences. Here are some helpful booking tips for using Vrbo.

  • Traveling to Chesapeake Beach with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Chesapeake Beach with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable 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 Chesapeake Beach: For many, a family vacation isn't truly satisfying without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Chesapeake Beach: If you’re searching for vacation rentals with special offers 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 rentals. 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 Beach

Chesapeake Beach offers a delightful getaway with its stunning ocean views and charming beachside setting. Perfect for families and couples alike, you can enjoy a range of activities from relaxing on the sand to exploring unique local spots. The friendly atmosphere and picturesque scenery make it an ideal destination for creating lasting memories. Experience the vibrant vibe of Chesapeake Beach and its surrounding areas during your unforgettable vacation.

  • North Beach: Located merely 1.4km from Chesapeake Beach, North Beach is a charming coastal city known for its delightful outdoor experiences and scenic views. Visitors can enjoy a stroll along the picturesque boardwalk, which offers stunning vistas of the Chesapeake Bay. The recreational areas are perfect for families looking to spend quality time together, and the local shopping mall centre presents a variety of stores and eateries. Don't miss the nearby family beach and the serene national state park, both ideal for a fun-filled day in nature.
  • Deale: Situated 9.7km away from Chesapeake Beach, Deale is the go-to destination for outdoor enthusiasts and adventurers alike. This vibrant city is surrounded by beautiful landscapes, including beaches and lakes, making it perfect for those seeking scenic getaways. The recreational areas provide ample opportunities for activities such as fishing and kayaking, while the local shopping centre offers a selection of shops and dining options. The nearby national state park is also a must-visit, providing trails and natural beauty to explore.
  • Rose Haven: Just 3.2km from Chesapeake Beach, Rose Haven is a quaint village that caters to families and couples looking for a romantic escape. Known for its inviting water park and recreational areas, it’s a fantastic destination for a fun-filled day with loved ones. Visitors can explore the beautiful beaches, enjoy the tranquility of the local lake, and marvel at the historical monument. Rose Haven's charming atmosphere makes it a perfect spot for creating lasting memories in a picturesque setting.

Best time to go to Chesapeake Beach

If you're planning a trip to Chesapeake Beach, 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
January36.0°F (2.2°C)Light RainMostly SunnyLowSlightly Low
February38.3°F (3.5°C)Light RainMostly SunnyAverageSlightly Low
March45.0°F (7.2°C)Light RainMostly SunnyAverageSlightly Low
April55.2°F (12.9°C)Light RainMostly SunnyAverageAverage
May64.2°F (17.9°C)Light RainMostly SunnyAverageAverage
June73.0°F (22.8°C)Light RainMostly SunnyHighAverage
July78.1°F (25.6°C)Light RainMostly SunnyHighSlightly High
August76.5°F (24.7°C)Light RainMostly SunnyHighSlightly High
September70.7°F (21.5°C)Light RainMostly SunnyAverageSlightly High
October60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
November48.9°F (9.4°C)Light RainMostly SunnyLowAverage
December41.7°F (5.4°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is simple

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

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient platform for you to plan new adventures, refine your current plans, or manage your bookings. Your saved or reserved properties are thoughtfully categorized into Potential, Upcoming, or Current Trips, making it easy to stay organized. To discover the features of Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Explore the beachside setting in Chesapeake Beach

Enjoy the live music and other features of Chesapeake Beach. This relaxing and romantic city is known for its restaurants, spas and beaches. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Chesapeake Beach

Are you hoping to discover attractions to see in the city? Venture out of your vacation home and experience everything that makes Chesapeake Beach a fun place to get away. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Chesapeake Beach Water Park (0.2 mi / 0.3 km)
  • Fridays Creek Winery (7.6 mi / 12.2 km)
  • Running Hare Vineyard (13.6 mi / 21.9 km)
  • Lake Presidential Golf Club (14.9 mi / 24 km)
  • South River Golf Links (15.7 mi / 25.2 km)
  • Renditions Golf Club (16.5 mi / 26.6 km)

Exploring the natural features in Chesapeake Beach

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Chesapeake Beach is a great place to get out in nature. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Breezy Point Beach (5.2 mi / 8.3 km)
  • Merkle Wildlife Sanctuary (9.6 mi / 15.5 km)
  • Shadyside Park (10.6 mi / 17 km)
  • Triton Beach (13.3 mi / 21.3 km)
  • Smithsonian Environmental Research Center (13.4 mi / 21.6 km)
  • Battle Creek Cypress Swamp Sanctuary (14.4 mi / 23.1 km)

Seasonal weather averages in Chesapeake Beach

If warm-weather activities are high on your list, July, August, June and September are the hottest months to visit, when temperatures average 75°F.

How to get to and around Chesapeake Beach

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 26.5 mi (42.7 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to College Park, MD (CGS), which is 28.8 mi (46.3 km) away.

Frequently asked questions

What is the best area to stay in Chesapeake Beach when booking a vacation rental?
When considering a vacation rental in Chesapeake Beach, Maryland, the most appealing area to stay in is the waterfront neighbourhood. This charming locale not only offers stunning views of the Chesapeake Bay but also provides easy access to various attractions. One of the top highlights in this area is the Chesapeake Beach Water Park, great for families looking to enjoy a day of fun and relaxation. Additionally, the nearby Boardwalk and Fishing Pier are excellent spots for leisurely strolls and catching a glimpse of local wildlife.

Another attractive option is the area around the Calvert Cliffs State Park, which is renowned for its hiking trails and fossil hunting opportunities along the stunning coastal cliffs. Staying here allows visitors to immerse themselves in nature while still being close to the quaint shops and restaurants that characterise Chesapeake Beach.
How much does it cost to rent a vacation home in Chesapeake Beach?
Prices for vacation rentals in Chesapeake Beach 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 travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chesapeake Beach to more spacious homes.
Are there any discounts for Chesapeake Beach vacation house rentals?
You can find great discounts on house rentals in Chesapeake Beach 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 Beach?
For renting a beach house in Chesapeake Beach, consider the scenic waterfront areas along the Chesapeake Bay. The vicinity near the Chesapeake Beach Railway Trail offers a delightful mix of beach access and recreational opportunities. Many properties in this area feature amenities such as spacious decks with bay views, private yards, and outdoor grilling areas, making them superb for family gatherings or relaxing getaways.

The area around the Boardwalk is particularly appealing, where travellers can find charming beach cottages and larger homes that often come equipped with modern kitchens, comfortable living spaces, and easy access to the sandy shores. This location allows visitors to enjoy local attractions such as the Chesapeake Beach Water Park and various shops and restaurants, enhancing the overall experience.
What is the most popular type of vacation rental accomodation in Chesapeake Beach?
In Chesapeake Beach, vacation houses and cottages are the most popular types of rental accommodations, with several available throughout the area. These properties provide a charming, home-like atmosphere, ideal for families or groups looking to enjoy the local beaches and waterfront activities. Most vacation houses come equipped with multiple bedrooms, fully stocked kitchens, and spacious living areas, often featuring outdoor spaces like decks or patios where guests can relax and enjoy the coastal breeze. Cottages, on the other hand, tend to offer a cozier experience, with comfortable interiors and convenient access to nearby attractions such as the Chesapeake Beach Water Park and local dining options.
Are there any family house rentals in Chesapeake Beach?
In Chesapeake Beach, there are about ten family-friendly house rentals available, making it an excellent choice for those travelling with children. The area is known for its charming waterfront views and a relaxed atmosphere, superb for family outings. Many of these properties offer spacious living areas, fully equipped kitchens, and outdoor spaces where kids can play safely.
Can I rent a vacation home with a pool or hot tub in Chesapeake Beach?
In Chesapeake Beach, there are several vacation homes available for rent that come equipped with pools and hot tubs, making it an appealing destination for those looking to enjoy a relaxing getaway. This charming coastal town, located along the western shore of the Chesapeake Bay, features properties in various neighbourhoods, providing a mix of beachfront access and tranquil surroundings.
Can I find long-stay vacation rentals in Chesapeake Beach?
A long-stay vacation rental in Chesapeake Beach 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 pet-friendly house rentals in Chesapeake Beach?
In Chesapeake Beach, there are several pet-friendly house rentals available, making it a welcoming destination for travellers with pets. The area features charming waterfront properties that often include amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can roam. Many of these rentals come with private decks or patios, great for enjoying the serene views of the Chesapeake Bay.
Are there any remote work vacation rentals in Chesapeake Beach?
In Chesapeake Beach, Maryland, there are several remote work vacation rentals available that cater to those looking to combine work and leisure. Many properties in this charming coastal town come equipped with essential amenities including Wi-Fi, dedicated desks, and comfortable office chairs, making it easy for travellers to maintain productivity while enjoying their stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chesapeake Beach vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Chesapeake Beach 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 Chesapeake Beach?
In Chesapeake Beach, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature patios, providing a lovely outdoor space for relaxation or dining al fresco. Additionally, rentals typically come with cookware, dishware, and utensils, making it convenient for travellers to enjoy home-cooked meals. Microwaves are commonly available as well, adding to the comfort and functionality of these vacation rentals.
When is the best time to visit Chesapeake Beach for a vacation rental?
The best time to book a vacation rental in Chesapeake Beach is during the summer months, specifically from June to August, when the beach comes alive with vibrant energy and activities. July stands out as the most popular month, drawing families and beach enthusiasts eager to enjoy the warm weather and indulge in water sports, fishing, and beachside relaxation.

During this peak season, temperatures typically hover in the mid to high 20s Celsius, providing the great climate for swimming, sunbathing, and seaside picnics. The bustling atmosphere creates a wonderful environment for socialising and making memories, whether you're strolling along the boardwalk or enjoying fresh seafood at local restaurants.

For those looking to experience Chesapeake Beach without the summer crowds, consider visiting in December. While this month falls into the low season, it offers a unique charm with fewer tourists, allowing for a more tranquil experience. You can enjoy peaceful walks along the shore and explore the area's winter festivities, all while benefiting from potentially lower rental rates.
How early should I book a Chesapeake Beach vacation rental?
Book your Chesapeake Beach 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.
Can I change or cancel my Chesapeake Beach home rental booking on Vrbo?
To find Chesapeake Beach 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 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 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 Beach 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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