Discover a selection of 396 vacation rentals in Chesapeake Beach, MD that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $94 per night, and houses and cabins are popular options for a stay in Chesapeake Beach. Either way, you'll find a rental for everyone's needs.
Destination guide

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.

Things to do

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.


Sand, sun, and a freshly caught crab – a classic beach day

Set on the shores of the bay, your Chesapeake Beach vacation rental is a great way to visit, well, the beach! Breezy Point Beach and Campground is a half-mile of sand and sun, with a fishing pier, a playground for kids, and a picnic area. It's a great spot for crabbing, too. If you'd rather cast your line from a boat deck, marinas in town offer charter boat fishing. The local resort features a gaming room and bingo, and when you're finally tuckered out, you can unwind by camping under the stars.


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.

Natural features

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 there

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 might consider flying into College Park, MD (CGS), which is 28.8 mi (46.3 km) away.

How many vacation rentals are available around Chesapeake Beach, MD?

Our 2020 property listings offer a large selection of 396 vacation rentals around Chesapeake Beach. From 317 house rentals to 28 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Chesapeake Beach?

Vrbo offers a large selection of vacation rentals near lovely places in Chesapeake Beach. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Chesapeake Beach Railway Museum: 240 vacation rentals
  • Chesapeake Beach Water Park: 261 vacation rentals
  • Rod n Reel Charter Fishing: 239 vacation rentals
  • Calvert Cliffs State Park: 96 vacation rentals
  • Maryland Quiet Waters Park: 538 vacation rentals

But there are many other points of interest around Chesapeake Beach listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Chesapeake Beach?

Yes, of course. Vrbo has 317 Houses in Chesapeake Beach. Our other popular types of vacation rentals in Chesapeake Beach include:

  • Cabins: 28 rentals available
  • Cottages: 28 rentals available
  • Bungalows: 28 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool in Chesapeake Beach?

Yes, you can select your preferred vacation rental with pool among our 69 vacation rentals with pool available in Chesapeake Beach. Please use our search bar to access the selection of vacation rentals available.

    Explore destinations around Chesapeake Beach