Discover a selection of 357 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 kitchens. Prices start at $120 per night, and houses and cottages 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 357 vacation rentals around Chesapeake Beach. From 232 house rentals to 31 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a city-center property in Chesapeake Beach?

Roll straight out of bed and walk to those must-visit attractions. Or simply jump straight into the hustle and bustle of the city! Spend your next trip in the heart of the main streets, with city centre accommodation. Vrbo has 85 centrally located vacation rentals available. Of course, that might not be your style. Luckily, Vrbo has plenty more options, including:

  • 77 water-view vacation rentals.
  • 68 shore-front vacation rentals.
  • 34 waterfront vacation rentals.

Can I rent a house in Chesapeake Beach?

If you want to have an authentic local experience and love having lots of space to spread out, renting an entire house is the way to go. There are 309 options currently listed on Vrbo. Prices start at $60 per night. If that doesn't suit your group's style, we've got a range of different rental options to pick from, such as:

  • Apartment: 40 vacation homes. Prices start from $63 per night.
  • Condo: 33 vacation homes. Prices start from $67 per night.
  • Townhome: 33 vacation homes. Prices start from $33 per night.

Can I stay in Chesapeake Beach in a large group?

It can be tricky finding the time to relax with your extended family and friends. A trip away is a perfect opportunity to reunite and unwind. If you were hoping to kick back under the same roof, Vrbo has places to suit. House vacation homes are the most popular option for large groups of visitors, with 46 featured here. The rental options that can provide for large groups around here include:

  • Are you on the hunt for vacation homes that can house 6 guests? We have 156 that will be ideal. Prices start from $48 per night.
  • Require a place for 10 guests? We have 114 that will serve you well. Prices start from $257 a night.
  • Planning a trip away with 8 guests? We've got 107 vacation homes that will be ideal. Prices start from $120 per night.

You and all your buddies will be well catered to when you book your Chesapeake Beach travels with us!

Where are the cheapest rentals in Chesapeake Beach?

Give the flick to boring cookie-cutter hotel chains! Indulge in the freedom of staying like a local in an affordable rental instead. Have a look at the fabulous options available for you now on Vrbo. Murray Hill has bargain written all over it. And with 84 Vrbo rentals at an average price of $393 a night, it isn't hard to see why. You'll find another 160 Vrbo rentals waiting for you in or around Eastport. The average price in this area is $402 per night.

Explore destinations around Chesapeake Beach