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.

Where to stay around Chesapeake Bay?

Our 2019 property listings offer a large selection of 6,205 vacation rentals near Chesapeake Bay. From 2,568 Houses to 316 Cabins, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Chesapeake Bay for a holiday or a weekend are on HomeAway.

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 HomeAway travelers, the most popular destinations to visit are:

  • Ocean City: 5,430 vacation rentals
  • Outer Banks: 5,897 vacation rentals
  • Virginia Beach: 1,617 vacation rentals
  • Corolla: 2,229 vacation rentals
  • Rehoboth Beach: 3,406 vacation rentals

And HomeAway 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: 5,430 rentals
  • Virginia Beach: 1,617 rentals
  • Corolla: 2,229 rentals
  • Rehoboth Beach: 3,406 rentals
  • Cape May: 1,996 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): 5,428 vacation rentals
  • Ronald Reagan Washington National Airport (DCA): 2,058 vacation rentals
  • Baltimore-Washington International Thurgood Marshall Airport (BWI): 727 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?

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

  • Rehoboth Beach Boardwalk: 2,888 rentals
  • Bethany Beach Boardwalk: 3,402 rentals
  • Assateague Island National Seashore: 5,290 rentals
  • United States Capitol: 2,036 rentals
  • Cape Charles Beach: 201 rentals

But there are many other points of interest around Chesapeake Bay listed on HomeAway 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
5,430 vacation rentals
Virginia Beach
1,617 vacation rentals
2,229 vacation rentals
Rehoboth Beach
3,406 vacation rentals
Cape May
1,996 vacation rentals
Bethany Beach
6,150 vacation rentals
2,585 vacation rentals
Washington DC
1,999 vacation rentals
Dewey Beach
2,011 vacation rentals
1,095 vacation rentals
551 vacation rentals
Wildwood Crest
2,391 vacation rentals
Chincoteague Island
205 vacation rentals
Fenwick Island
5,491 vacation rentals
3,303 vacation rentals
527 vacation rentals
Cape Charles
189 vacation rentals
292 vacation rentals
159 vacation rentals
766 vacation rentals