Chesapeake Beach vacation rentals

We found 837 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:Jul 24 - Jul 31

Image gallery for USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR

View from the front of this Stately Masterpiece (you'd think I built it ;-)
8.0 out of 10, Very Good, (5 reviews)
Very Good
(5 reviews)

USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR

Annapolis

17% off
Price is $1,099
$7,693 for 7 nights
All fees included
USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR

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Find out more about Chesapeake Beach

Why visit Chesapeake Beach

  • Scenic Beauty: Enjoy breathtaking views of the Chesapeake Bay and its stunning waterfront estates.
  • Outdoor Adventures: Engage in various recreational activities like swimming, fishing, and hiking in nearby parks.
  • Family-Friendly Atmosphere: Experience a welcoming community perfect for family vacations with activities for all ages.
  • Charming Coastal Town: Explore the quaint shops and local eateries that enhance the town's unique character.
  • Diverse Accommodations: Choose from cozy cottages to spacious villas that cater to your vacation needs.

Popular types of accommodation in Chesapeake Beach

Looking for the perfect getaway in Chesapeake Beach? You're in the right place. Our most popular vacation rentals include houses, cozy cottages, and stylish apartments. Whether you're seeking spacious villas or charming homes for rent, we have a variety of Maryland vacation rentals to suit your needs. Experience the beauty of Chesapeake Beach with accommodations that offer transparency, savings, and peace of mind.

  • Houses: These spacious homes offer a private retreat, perfect for families or groups looking to enjoy Chesapeake Beach together.
  • Cottages: Charming and cozy, cottages provide a quaint atmosphere for a relaxing getaway by the water.
  • Apartments: Conveniently located, apartments are ideal for travelers seeking a home-like stay with easy access to local attractions.
  • Condos: Modern condos offer amenities and stunning views, making them a popular choice for vacationers.
  • Cabins: Rustic cabins provide a unique experience, perfect for those who want to immerse themselves in nature.**

Top attractions in and around Chesapeake Beach

Chesapeake Beach, Maryland, offers a perfect blend of outdoor adventures and scenic beauty for a memorable beach vacation. Visitors can explore the picturesque Chesapeake Bay and enjoy local attractions like parks and beaches. Whether you're seeking family-friendly activities or eco-conscious experiences, this charming destination has it all. Don’t miss the chance to discover the natural beauty of Chesapeake Beach and nearby Virginia Beach for a well-rounded getaway.

  • Breezy Point Beach: Enjoy the serene beach vibes at Breezy Point Beach, a perfect spot for sunbathing, swimming, and relaxing by the water. Its picturesque views make it an ideal getaway for beach lovers.
  • Rod n Reel Charter Fishing: Experience adventure at Rod n Reel Charter Fishing, where you can embark on fishing excursions. This marina offers outdoor fun with opportunities to catch a variety of fish while enjoying the beautiful seaside.
  • Bayside History Museum: Delve into local culture at the Bayside History Museum, located just 0.8 miles from Chesapeake Beach. Discover the area's rich history through engaging exhibits and artifacts.

Things to do recommended for couples

For a romantic getaway in Chesapeake Beach, consider a visit to Old South Country Club, located 11 miles away. This luxurious private club offers a serene atmosphere perfect for couples to unwind and enjoy each other's company amid beautiful surroundings.

Things to do recommended for families

Families visiting Chesapeake Beach can enjoy a thrilling day at the Chesapeake Beach Water Park, explore the beautiful beaches, and take a scenic ride on the historic Chesapeake Beach Railway Trail, perfect for biking and walking with kids.

Things to do recommended for groups

Groups visiting Chesapeake Beach can enjoy a relaxing day at the Chesapeake Beach Water Park, savor fresh seafood at local restaurants, and take a scenic boat tour on the Patuxent River for stunning views and wildlife sightings. Don’t miss the charming boardwalk for a fun evening stroll.

*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

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 for you.

  • Traveling to Chesapeake Beach with a group: Think about how many bedrooms you require, as well as features like a complete kitchen or outdoor areas for group gatherings. The good news is that you can easily filter for all these options and more on Vrbo.
  • Traveling to Chesapeake Beach 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 Chesapeake Beach: For many families, a getaway wouldn't be the same without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Most 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 Beach: If you're in search of vacation rentals with discounts 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 parking, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Chesapeake Beach

Chesapeake Beach, Maryland, offers a delightful escape for those seeking a relaxing beach vacation. With stunning waterfront estates and easy beach access, visitors can soak in the scenic beauty of the Chesapeake Bay area. Explore the charming coastal town's family-friendly atmosphere and indulge in recreational activities while experiencing a romantic vibe. Nearby neighborhoods further enhance your travel experience with their friendly locals and picturesque surroundings, making Chesapeake Beach an ideal destination for your getaway.

  • Upper Marlboro: Located approximately 14 miles from Chesapeake Beach, Upper Marlboro is a charming city that offers a blend of family-friendly activities and urban experiences. Visitors can enjoy outdoor activities at local parks and sports facilities, making it a great spot for sports enthusiasts. The city features shopping centers and malls for a fun shopping spree, along with educational attractions that can enrich your visit. With its urban parks and stadiums, Upper Marlboro is perfect for those looking to engage in lively city experiences while still enjoying the tranquility of nature.
  • North Beach: Just 0.9 miles from Chesapeake Beach, North Beach is a delightful coastal town renowned for its stunning scenery and beach activities. This charming destination is perfect for outdoor lovers, with a picturesque boardwalk that invites leisurely strolls and beautiful views of the bay. Visitors can explore recreational areas and enjoy family-friendly beaches, making it an ideal spot for a relaxing day by the water. North Beach’s vibrant shopping scene adds to its appeal, making it a must-visit for those seeking a mix of relaxation and fun.
  • Rose Haven: Located 2 miles from Chesapeake Beach, Rose Haven is a quaint village that offers a serene beach experience. Known for its beautiful scenery, it’s a fantastic place to enjoy outdoor recreation, including access to parks and lakes. Visitors can engage in educational activities or simply relax by the water, soaking in the natural beauty. The local shopping centers provide a charming touch to the village, making it a lovely destination for those looking to unwind and explore the coastal charm of Maryland.

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 SunnyHighSlightly High
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 SunnyAverageAverage
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 a breeze

Are you hoping to save on your upcoming trip? It’s a great idea to be flexible with your travel dates, as prices can vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, resume where you left off, or manage your travel arrangements. You’ll see your saved or booked properties organized under categories like Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Chesapeake Beach, a railway hub that became a bayside escape

Founded by the Washington and Chesapeake Bay Railway Company in 1894 as a resort destination for visitors from Washington D.C., Chesapeake Beach was once a party city. It boasted beachfront hotels, a racetrack, a casino, a bathhouse, and a 1600-foot boardwalk built over the water. With the end of the railroad era came a new identity, and today, your Chesapeake Beach vacation rental sits in a quieter, family-friendly beach community with charter fishing boats and beautiful views. Less than 3 miles square, Chesapeake Beach is the perfect little getaway.

See a vintage bathing suit before taking yours to the pool

The trains may no longer be running toward your Chesapeake Beach vacation rental, but you can still visit the old station, now the Chesapeake Beach Railway Museum. The exhibits depict the thriving history and life of the railway with pictorial displays, oral histories, artefacts, and authentic period clothing. The museum also hosts events for kids and a summer concert series. When you're ready for some more watery action, try out Chesapeake Beach Water Park and its 8 waterslides, kids activity pool, waterfalls, fountains, and lagoons. You're sure to head home informed and exhausted.

Bustling, sunny summers with a rain shower or two – or ten

Chesapeake Beach lies in Maryland's humid subtropical climate zone. Hot, muggy summers, with temps hitting the high 80s and low 90s, are followed by mild to chilly winters. Rain is in the forecast year-round, so bring rain gear and a board game or two for those unpredictable summer showers. Vacationers are less likely to visit the bay in winter, when it's too cold to swim or bask in the sun, so book your rental then if you seek lower prices and more peace and quiet by the water.

Wetlands, wetlands, and more wetlands

The mild weather and water make Chesapeake Beach a hot spot for all kinds of wildlife. See some examples along the Chesapeake Beach Railway Trail. This boardwalk trail is easy to navigate and features educational plaques pointing out marsh plants, seabirds, and other features of the surrounding water and marshland. If that's not enough wetland for you, the Wetlands Overlook Park is less than 2 miles from Chesapeake Beach. The park has a pier and two gazebos where visitors can sit and relax while looking for wildlife and photographing the landscape.

How to get to and around Chesapeake Beach

Fly into Ronald Reagan Washington National Airport (DCA), the closest airport, located 29.4 mi (47.3 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 26.5 mi (42.7 km) away.

Frequently asked questions

What is the best area to stay in Chesapeake Beach, Maryland, United States of America when booking a vacation rental?
When considering a vacation rental in Chesapeake Beach, Maryland, a popular area to stay is near the waterfront, where you can enjoy stunning views and easy access to the beach. This charming area is home to a variety of vacation properties, ranging from cozy cottages to more spacious homes, making it ideal for families and groups looking for a relaxing getaway.

A highlight of staying here is the proximity to attractions such as the Chesapeake Beach Water Park, which is a fantastic spot for families, featuring water slides and a lazy river. Additionally, the nearby North Beach offers a lovely boardwalk and charming shops, great for leisurely strolls and local dining experiences.
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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
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, travelers should focus on the waterfront neighborhoods along the Chesapeake Bay. The area near the Chesapeake Beach Railway Museum offers convenient access to the sandy shores and local attractions. Many beach houses in this vicinity come with amenities such as spacious decks, outdoor grills, and private beach access, ideal for families or groups looking to enjoy a seaside retreat.

Additionally, the area around the North Beach Boardwalk offers charming vacation rentals that provide stunning views of the bay, along with amenities like beachfront patios and fire pits, great for evening gatherings. This neighborhood is also close to local shops, cafes, and restaurants, ensuring that guests have everything they need for a comfortable stay.

For those seeking a more tranquil experience, the southern parts of Chesapeake Beach feature secluded properties with lush landscaping and easy access to nature trails. Many of these rentals are equipped with modern kitchens, cozy living areas, and sometimes even hot tubs, making them great for relaxation after a day of exploring the beach or nearby parks.
What is the most popular type of vacation rental accomodation in Chesapeake Beach?
In Chesapeake Beach, cottages are a popular choice among travelers, with several available throughout the area. These charming properties typically offer a cozy atmosphere, superb for enjoying the coastal vibe. Most cottages come with fully equipped kitchens, comfortable living spaces, and often outdoor decks or patios where guests can relax while taking in views of the bay.

Vacation houses are also plentiful, providing more space for families or groups. These homes generally feature multiple bedrooms, spacious living areas, and private yards, making them ideal for gatherings and outdoor activities. Additionally, several apartments are available, which cater to those looking for a more compact stay while still enjoying essential amenities.
Are there any family house rentals in Chesapeake Beach?
In Chesapeake Beach, there are several family-friendly house rentals available, making it a wonderful destination for groups looking to enjoy some quality time together. Many of these homes are situated close to the waterfront, offering easy access to the beach and stunning views of the Chesapeake Bay. Visitors can find spacious living areas, fully equipped kitchens for family meals, and outdoor decks or patios great for relaxation or barbecues.

The town is not only known for its beautiful beaches but also for attractions like the Chesapeake Beach Water Park, which is a great spot for children to have fun. Families can also explore local parks and playgrounds nearby, providing plenty of outdoor activities.
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 with pools and hot tubs, making it an attractive option for travelers looking for relaxation and fun. This charming coastal town offers a mix of waterfront properties and homes located among the trees, providing picturesque views and a serene environment. Many of these rentals feature private pools, hot tubs, and spacious outdoor patios where guests can unwind and enjoy the beautiful surroundings. Inside, travelers can expect well-equipped kitchens, comfortable living areas, and amenities like Wi-Fi and air conditioning, ensuring a pleasant stay.
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. 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 Beach?
In Chesapeake Beach, there are several pet-friendly house rentals available, making it a great destination for travelers looking to bring their furry friends along. Many of these vacation homes feature inviting amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can play.

The area is known for its beautiful waterfront and offers easy access to the Chesapeake Bay, with nearby parks and beaches that welcome pets. The boardwalk and local parks provide ample opportunities for walks and outdoor activities, ensuring both pets and their owners can enjoy the scenic surroundings. Additionally, some rentals may include features like fenced yards or pet-friendly furnishings, adding to the comfort of your stay.
Are there any remote work vacation rentals in Chesapeake Beach?
In Chesapeake Beach, there are several remote work-friendly vacation rentals available, suiting those looking to balance work and leisure. Many properties offer essential amenities such as Wi-Fi in rooms and common areas, ensuring a reliable internet connection for remote working needs. Travelers can expect comfortable accommodations with dedicated workspaces, ideal for productivity.

The waterfront location of Chesapeake Beach also provides a serene backdrop for breaks, with stunning views of the Chesapeake Bay. Nearby attractions include the local boardwalk and beaches, great for unwinding after work hours. 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 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 Beach?
In Chesapeake Beach, popular vacation rental amenities include kitchens, which allow guests to prepare their own meals, and outdoor spaces such as decks or patios, superb for enjoying the fresh air and scenic views. Many rentals also feature balconies, providing additional outdoor relaxation options. Air conditioning is commonly found in these properties, ensuring a comfortable stay during warmer months, while fireplaces add a cozy touch for cooler evenings.
When is the best time to visit Chesapeake Beach for a vacation rental?
The peak travel season in Chesapeake Beach occurs from June to August, making it a vibrant time for families and beach enthusiasts seeking sun-soaked getaways. July, in particular, stands out as the most popular month, where visitors flock to enjoy the warm weather and partake in a variety of outdoor activities, from swimming in the Chesapeake Bay to indulging in fresh seafood at local eateries.

During this period, temperatures typically range from the mid-70s to low 90s Fahrenheit, providing ideal conditions for sunbathing, picnicking, and exploring the picturesque boardwalk. The lively option is great for those looking to socialize, with plenty of events and festivals adding to the summer charm.

For travelers seeking a more budget-friendly experience, consider planning your visit in December. While this month is outside the main tourist season, it offers a unique opportunity to enjoy the peaceful winter ambiance of Chesapeake Beach. This time of year, you can appreciate the serene beauty of the bay and partake in cozy indoor activities or holiday festivities without the crowds.

Ultimately, your ideal time to visit Chesapeake Beach will depend on whether you prefer the bustling summer fun or the tranquil, off-peak charm of winter.
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.
What are the top attractions in Chesapeake Beach, Maryland, United States of America?
In Chesapeake Beach, visitors can enjoy a variety of attractions that highlight the area's coastal charm and natural beauty. The Chesapeake Beach Railway Museum offers a glimpse into the region's history, showcasing artifacts from the old railway that once connected the town to Washington, D.C. The nearby Chesapeake Beach Water Park is a family-friendly destination featuring water slides and pools, great for a fun day in the sun.

For those who enjoy outdoor activities, the boardwalk along the beach provides scenic views and opportunities for fishing and crabbing. The area is also known for its local seafood restaurants, where visitors can savor fresh catches. Additionally, the nearby Calvert Cliffs State Park is a great spot for hiking and fossil hunting along the shoreline, attracting nature enthusiasts and families alike.
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 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 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.
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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