Photo by Ronanne Vinson

Chesapeake Beach vacation rentals

We found 837 vacation rentals — enter your dates for availability

Discover a selection of 9 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:Aug 22 - Aug 29
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Find out more about Chesapeake Beach

Find out more about Chesapeake Beach

Why visit Chesapeake Beach

  1. Outdoor Adventures: Experience a variety of recreational activities, from hiking in state parks to beach fun along the Chesapeake Bay.
  2. Charming Accommodations: Choose from cozy beach cottages to modern apartments, perfect for a relaxing getaway.
  3. Family-Friendly Attractions: Enjoy activities suitable for all ages, ensuring a memorable experience for the whole family.
  4. Scenic Views: Take in breathtaking landscapes along the Eastern Shore, ideal for romantic getaways and picturesque moments.
  5. Vibrant Community: Engage with friendly locals and explore a welcoming atmosphere that enhances your vacation experience.

Popular types of accommodation in Chesapeake Beach

If you're looking for the perfect getaway in Chesapeake Beach, you're in the right place! Our most popular accommodation options include charming houses, cozy apartments, and delightful cottages. Whether you're dreaming of a beachfront house, a Chesapeake Beach home, or a stylish condo in Annapolis, we've got a range of options to suit your needs. Experience the beauty and relaxation of Chesapeake Beach with the assurance of finding the ideal rental for your vacation.

  • Houses: The top choice for visitors seeking spacious and comfortable stays, ideal for families or groups in Chesapeake Beach.
  • Apartments: A popular option for those looking for a cozy, self-contained living space close to local attractions.
  • Cottages: Charming and quaint, these rentals offer a rustic experience near the shoreline.
  • Condos: A modern choice providing amenities and often great views, perfect for a relaxing getaway.
  • House Boats: A unique way to stay on the water, combining adventure and comfort in Chesapeake Beach.**

Top attractions in Chesapeake Beach

Chesapeake Beach is perfect for outdoor enthusiasts and families seeking scenic getaways. Explore a variety of attractions, including state parks, historic homes, and universities that offer rich cultural experiences and adventurous activities. Whether you're looking for adventure or a relaxing retreat, Chesapeake Beach has something for everyone to enjoy.

  1. Rod n Reel Charter Fishing: Experience the thrill of deep-sea fishing with Rod n Reel Charter Fishing. Situated in Chesapeake Beach, this marina offers adventure and outdoor fun, making it perfect for both novice and experienced anglers looking to catch a variety of fish while enjoying the scenic waters.
  2. Breezy Point Beach: Relax at Breezy Point Beach, where you can soak up the sun and enjoy the tranquil waters. This beautiful beach provides the perfect setting for swimming, sunbathing, and beach activities, all while embracing the laid-back beach vibes.
  3. Chesapeake Beach Railway Museum: Dive into local history at the Chesapeake Beach Railway Museum. This cultural gem showcases the rich railway heritage of the area, featuring fascinating exhibits and artifacts that tell the story of transportation and community in Chesapeake Beach.

Things to do recommended for couples

For a romantic getaway in Chesapeake Beach, explore Fridays Creek Winery for delightful wines and ambiance. Enjoy a fun round at R&J's PlayPark mini golf, or indulge in luxury at Old South Country Club. Each spot offers a unique experience perfect for couples looking to connect.

Things to do recommended for families

Your family will have a blast at the Chesapeake Beach Water Park, enjoying thrilling slides and pools. For sports lovers, Prince George's Stadium offers exciting games, while Allen Pond Park provides a serene space for relaxation and wellness, perfect for unwinding after a fun-filled day.

Things to do recommended for groups

Groups visiting Chesapeake Beach can enjoy a round of golf at Lake Presidential Golf Club, shop at Annapolis Harbour Center, and catch a performance at The Colonial Players theater, each offering unique experiences that blend sports, shopping, and culture for a fun-filled getaway.

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

When planning your trip—whether you're traveling with friends, family, pets, or seeking an extended stay—be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Chesapeake Beach with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and many 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 families, a trip just isn't the same without their furry companion. If you can relate, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chesapeake Beach: If you're seeking vacation rentals with great deals 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 options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Chesapeake Beach

Chesapeake Beach offers a delightful blend of outdoor adventures and family-friendly activities, perfect for a relaxing getaway. Explore the picturesque Eastern Shore, unwind in charming beach cottages, and visit nearby Bethany Beach for sun-soaked fun. With its scenic views and romantic atmosphere, you'll find the ideal vacation spots to create lasting memories. Enjoy friendly interactions and a vibrant community vibe as you embark on excursions that cater to both relaxation and recreation.

  • Annapolis: Located approximately 20 miles from Chesapeake Beach, Annapolis is a charming city renowned for its rich history and vibrant waterfront. Visitors are drawn to its historic district, where colonial architecture meets modern boutiques and eateries. The city offers various family-friendly activities, including visits to the United States Naval Academy and the Maryland State House. Annapolis is also a hub for outdoor enthusiasts, with options for sailing, biking, and exploring scenic parks. Don’t miss the chance to stroll along the waterfront and enjoy the local seafood at one of the many restaurants.
  • North Beach: Just 0.9 miles away from Chesapeake Beach, North Beach is a delightful coastal town that promises a relaxing getaway. Known for its picturesque boardwalk and family-friendly atmosphere, this charming destination is perfect for outdoor adventures and scenic walks along the beach. Enjoy recreational areas, local shops, and delicious eateries. The nearby Calvert Cliffs State Park offers hiking trails and fossil hunting opportunities, making it a great spot for nature lovers and families alike. With its beautiful beach and engaging community events, North Beach is a must-visit.
  • Rose Haven: Situated about 2 miles from Chesapeake Beach, Rose Haven offers a blend of family fun and entertainment. This small town features recreational areas, including parks and a water park, making it an ideal destination for families. Music concerts and community events often take place, providing a lively atmosphere. Visitors can also explore the local beach, enjoy views of the nearby lake, and visit historical monuments that add to the area’s charm. Rose Haven is perfect for those seeking a laid-back vacation experience with plenty of activities for everyone.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 SunnyAverageAverage
October60.4°F (15.8°C)Light RainMostly SunnyAverageSlightly High
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 vacation? Consider being flexible with your travel dates, as prices can fluctuate. Furthermore, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to refine your search by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on the full booking amount. Being the planner has its rewards! By becoming a member of our travel rewards program, One Key, you’ll gain access to exclusive discounts and accumulate OneKeyCash™ on qualifying reservations. Sign up today and begin enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient area to plan new trips, pick up right where you left off, or view and manage your travel arrangements. You can easily find properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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 most popular type of vacation rental accommodation in Chesapeake Beach?
The most sought-after types of vacation rentals in Chesapeake Beach are cottages. Looking for something different? Vrbo has plenty of options to match our guests’ unique needs, so you’ll see vacation homes in loads of sizes and shapes. The perfect home away from home is waiting for you — lock in yours today.
How much does it cost to rent a vacation rental in Chesapeake Beach?
Property type, season and length of stay are some of the conditions that can determine the price of a vacation home. Simply click on your travel dates to find your ideal fit. From homey country cottages to plush villas, all Vrbo vacation rentals provide incredible value.
How much does it cost to rent a beach house in Chesapeake Beach?
When you travel and the size and style of the property will influence the cost of your beachside vacation rental. Click on your Chesapeake Beach travel dates to view your options on Vrbo. Can’t live without a private pool? Use our filters to pick the features and amenities you want in your rental.
Are there pet-friendly vacation rentals in Chesapeake Beach?
With 12 properties that host four-legged guests, your furry best friend can join you on your Chesapeake Beach getaway. Use our filter tool to search our pet-friendly vacation rentals and find your pawfect pad on Vrbo.
Can I rent a house with a pool in Chesapeake Beach?
Add a whole other level of fun to your vacation by staying in one of the three houses with a private pool in Chesapeake Beach. Use our handy search filter to find the kind of property you want on Vrbo, and then spend carefree days splish-splashing around in a swimming pool that’s all your own.
What are popular rental amenities in Chesapeake Beach?
When it comes to rental amenities that people prefer in Chesapeake Beach, a beach view, a nearby river and a barbecue grill are at the top of the list. With Vrbo vacation rentals, there are choices to suit your taste and style, whether you’re going on a trip with your partner, your friends or even pets.
Are there large group vacation rentals in Chesapeake Beach?
Yes, you’ll find 11 vacation rentals in Chesapeake Beach that can sleep five or more guests. From family reunions to events like a friend’s birthday, these stays have enough room to hang out with the people you love.
Are there vacation rentals in Chesapeake Beach that welcome kids?
With 12 family-friendly vacation homes to select from in Chesapeake Beach, now is a superb time to introduce the kids to the thrills of travel. Check our “Properties good for families” filter box to search for stays that come with conveniences perfect for traveling families, such as dining rooms, backyards, entertainment areas and hot tubs.
What are the top attractions for families in Chesapeake Beach?
Keep your kids occupied at these awesome family-friendly attractions in Chesapeake Beach:

  • Breezy Point Beach
  • Chesapeake Beach Water Park
  • Chesapeake Beach Railway Museum

Can I find two-bedroom vacation rentals in Chesapeake Beach?
Gather your nearest and dearest and enjoy a relaxing escape in one of the seven two-bedroom vacation homes Chesapeake Beach has to offer.
Are there vacation rentals with WiFi in Chesapeake Beach?
Take your pick of five vacation rentals with WiFi in Chesapeake Beach. If you’d like to disconnect from the world on your trip, but still want to be connected to the web, these getaways have what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Chesapeake Beach?
Decide on your travel dates and then use our filters to look for vacation rentals with ac in Chesapeake Beach on Vrbo. With 12 air-conditioned properties available here, you can enjoy a cool and comfy break.
How old do you have to be to rent a vacation rental in Chesapeake Beach?
The minimum required age is generally 16, 18 or 21. It can differ across properties on Vrbo, so look at the rules of your preferred Chesapeake Beach vacation rental before booking your escape.
How long can I rent a vacation rental in Chesapeake Beach for?
The amount of time you can stay in a Chesapeake Beach vacation home for is down to each property. Just enter your travel dates to see options that offer long-term stays. They have everything you need to make your extended trip more comfortable such as air conditioning and laundries. Some properties might also offer weekly or monthly discounts, so you can stay longer for less money.
Does Vrbo offer discounts for vacation homes in Chesapeake Beach?
Weekend adventure or a much-needed extended escape, Vrbo has some bargain deals and special discounts in Chesapeake Beach to match your style and budget. Take a look at our weekly and monthly discounts on vacation rentals, or check out what’s just been added with one of our newly listed homes. Whatever it is you’re after, you’ll find the ideal place to stay — without draining your wallet.

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