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We found 5,962 vacation rentals — enter your dates for availability
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 private pools. 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 2021 property listings offer a large selection of 5,962 vacation rentals around Chesapeake Bay. From 2,991 house rentals to 257 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.