Discover a selection of 5,000 vacation rentals in Chesapeake Bay, US 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 $140 per night, and houses and cabins are popular options for a stay in Chesapeake Bay. Either way, you'll find a rental for everyone's needs.
Destination guide

Stunning waterscapes in Chesapeake Bay

Straddling both Maryland and Virginia, Chesapeake Bay takes the crown of the largest estuary in the United States. Its shoreline is dotted with rolling farmlands and lush wetlands, as well as a handful of state parks and sandy beaches. You'll also find a handful of friendly towns and villages, each with their own unique personalities. Just across the Chesapeake Bay Bridge is the Eastern Shore, famous for its mouth-wateringly fresh seafood. If you want to reel in your own catch of the day, Chesapeake Bay vacation rentals unlock access to a stunning line-up of waterfront properties on the Eastern Shore.

Things to do

Chesapeake Bay and the Star-Spangled Banner

Virginia's Chesapeake Bay region is brimming with history, from the birthplace of founding father George Washington to the estate of Confederate General Robert E. Lee. The Chesapeake Bay Maritime Museum in St. Michaels offers a glimpse at the region's colorful history, while mighty Fort McHenry served as the inspiration for America's beloved Star-Spangled Banner anthem. Beyond history, Chesapeake Bay boasts one of Virginia's most prestigious vineyards. Tucked away on the Northern Neck, Ingleside crafts award-winning reds, whites, and sparkling wine. With Chesapeake Bay vacation rentals you can stock up on your favorite blends then make a sunset toast on your own private deck.


Make a splash in Chesapeake Bay

Whether you want to paddle through Rocky Point State Park, kayak around the Chesapeake Ship Graveyard, or sign up for a hands-on fishing charter, there are endless opportunities to get your feet wet. Known as America's Sailing Capital, Annapolis is one of the bay's liveliest settlements. The historic city is anchored by a sprawling dock that attracts luxury yachts, high-speed powerboats, and everything in-between. Day trips to places like Smith Island, Oxford, and Chestertown offer a unique glimpse at colonial America, while Baltimore's Fells Point neighborhood serves up the bay's trendiest caf_s, bar, and restaurants.


Stay cool in Chesapeake Bay

Summer brings peak season in Chesapeake Bay, when flocks of vacationers descend on the region. Temperatures can creep into the 90s which makes waterfront Chesapeake Bay vacation rentals a great way to stay cool. If you want to beat the crowds, fall brings cooler weather and occasional rain. Every spring the state throws its annual Virginia Arts Festival, with most of Chesapeake Bay's towns and villages getting involved. Winter in Chesapeake Bay is wonderfully quiet, which makes it a fantastic time to relax, unwind, and chat to locals.

Natural features

Enjoy world-class birdwatching in Chesapeake Bay

Branching off the Atlantic Ocean, Chesapeake Bay is North America's largest estuary. It stretches for around 200 miles, which means there's a wealth of shoreline to explore. The seafood scene is legendary, with local specialties including blue crabs, clams, and oysters. The surrounding islands and wetlands also offer world-class birdwatching. From ospreys to bald eagles, the marshlands of Blackwater National Wildlife Refuge attract flocks of migratory birds traveling the Atlantic Coast.

How to get there

Traveling to and around Eastern Shore

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 15.2 mi (24.5 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Georgetown, DE (GED-Sussex County), which is 26.9 mi (43.2 km) away.

If you prefer train travel, you can make your way to Perryville Station.

How many vacation rentals are available around Chesapeake Bay, US?

Our 2020 property listings offer a large selection of 5,311 vacation rentals around Chesapeake Bay. From 2,803 house rentals to 284 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 most popular destinations to visit in Chesapeake Bay?

There are many lovely places to stay for a holiday trip or just for a weekend in Chesapeake Bay. From Vrbo travelers, the top most popular destinations to visit are:

  • Ocean City: 5,189 vacation rentals
  • Midtown Ocean City: 1,720 vacation rentals
  • Bethany Beach: 5,831 vacation rentals
  • Northeast Virginia Beach: 561 vacation rentals
  • Rehoboth Beach: 3,287 vacation rentals

And Vrbo offers you the chance to discover many other popular destinations in Chesapeake Bay! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in Chesapeake Bay?

Whether you're traveling with family or friends, here are the cities with the largest selection of vacation rentals for a holiday trip or just for a weekend in Chesapeake Bay:

  • Ocean City: 5,189 rentals
  • Bethany Beach: 5,831 rentals
  • Rehoboth Beach: 3,287 rentals
  • Cape May: 1,838 rentals
  • Wildwood: 2,389 rentals

For other cities, please use our search bar to access the selection of vacation rentals available.

Can I find easy-access vacation rentals when traveling by plane to Chesapeake Bay?

Yes of course. Our owners offer a large selection of vacation rentals near airports. The airports with a large selection of vacation rentals in Chesapeake Bay are:

  • Ocean City, MD (OCE-Ocean City Municipal): 5,177 vacation rentals
  • Frederick, MD (FDK-Frederick Municipal): 93 vacation rentals
  • Gettysburg, PA (GTY-Gettysburg Regional): 95 vacation rentals

For other airports, please use our search bar to access the selection of vacation rentals available.

Near which points of interest can I spend my holidays in Chesapeake Bay?

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

  • Virginia Beach Boardwalk: 1,035 rentals
  • Eastern Market: 39 rentals
  • Rehoboth Beach Boardwalk: 2,794 rentals
  • Silver Lake: 658 rentals
  • National Mall: 1,068 rentals

But there are many other points of interest around Chesapeake Bay listed on Vrbo where you can find your place to stay. Just write your wanted destination in our search bar and have a look at our selection.

Explore destinations around Chesapeake Bay

Ocean City
5,189 vacation rentals
Bethany Beach
5,831 vacation rentals
Rehoboth Beach
3,287 vacation rentals
Cape May
1,838 vacation rentals
2,389 vacation rentals
1,800 vacation rentals
551 vacation rentals
Ocean View
2,276 vacation rentals
Dewey Beach
1,841 vacation rentals
Virginia Beach
1,246 vacation rentals
Wildwood Crest
2,111 vacation rentals
210 vacation rentals
Cape Charles
153 vacation rentals
Ocean Pines
3,952 vacation rentals
230 vacation rentals
402 vacation rentals
Fenwick Island
5,257 vacation rentals
3,190 vacation rentals
2,839 vacation rentals
District of Columbia
1,805 vacation rentals