Discover a selection of 6,000 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 kitchens. Prices start at $120 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.
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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.

Activities

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.

Weather

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 5,640 vacation rentals around Chesapeake Bay. From 2,273 house rentals to 305 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: 5,236 vacation rentals
  • Outer Banks: 6,112 vacation rentals
  • Virginia Beach: 1,379 vacation rentals
  • Midtown Ocean City: 1,821 vacation rentals
  • Bethany Beach: 5,992 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: 5,236 rentals
  • Virginia Beach: 1,379 rentals
  • Bethany Beach: 5,992 rentals
  • Rehoboth Beach: 3,323 rentals
  • Washington DC: 1,942 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:

  • Philadelphia International Airport (PHL): 1,289 vacation rentals
  • Ocean City, MD (OCE-Ocean City Municipal): 5,233 vacation rentals
  • Frederick, MD (FDK-Frederick Municipal): 121 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: 970 rentals
  • Rehoboth Beach Boardwalk: 2,812 rentals
  • Assateague Island National Seashore: 5,086 rentals
  • United States Capitol: 2,010 rentals
  • Virginia Beach Town Center: 1,272 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
5,236 vacation rentals
Virginia Beach
1,379 vacation rentals
Bethany Beach
5,992 vacation rentals
Rehoboth Beach
3,323 vacation rentals
Washington DC
1,942 vacation rentals
Corolla
2,085 vacation rentals
Wildwood
2,512 vacation rentals
Wildwood Crest
2,206 vacation rentals
Williamsburg
592 vacation rentals
Cape May
1,915 vacation rentals
Ocean View
2,187 vacation rentals
Dewey Beach
1,999 vacation rentals
Philadelphia
1,295 vacation rentals
Chincoteague Island
234 vacation rentals
Cape Charles
177 vacation rentals
Ocean Pines
4,111 vacation rentals
Bumpass
227 vacation rentals
Villas
556 vacation rentals
Annapolis
347 vacation rentals
Fenwick Island
5,308 vacation rentals