Chesapeake Bay vacation rentals

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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.

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.

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 to and around Chesapeake Bay

The nearest airport is in Norfolk Intl. Airport (ORF), located 43.4 mi (69.8 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Newport News - Williamsburg Intl. Airport (PHF), which is 34.3 mi (55.2 km) away.

If you prefer to travel by train, Williamsburg Transportation Center, Newport News Station and Virginia Beach Station are the main stations in the city. You can get around Chesapeake Bay by catching a ride on the metro at Ft Norfolk-Medical Center Station, Newtown Road Station or York Street-Free Mason Station.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Chesapeake Bay?
According to our data, condos are considered the most popular property type in Chesapeake Bay. But of course, everyone’s idea of an awesome stay can vary. Vrbo has vacation homes with every size, shape and budget in mind, so you’re sure to find the perfect fit.
How much does it cost to rent a vacation rental in Chesapeake Bay?
Property type, length of stay and season are some of the things that can determine the price of a vacation home. Simply enter your dates of travel to find your perfect escape. From cozy chalets to expansive villas, all Vrbo vacation rentals offer terrific value.
How much does it cost to rent a beach house in Chesapeake Bay?
When you travel and the style and size of the property will influence how much you’ll pay for your beachside stay. Click on your Chesapeake Bay travel dates to see your options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use the filters to choose the features and amenities you want in your vacation home.
Are there pet-friendly vacation rentals in Chesapeake Bay?
Pack a bone and a squeezy toy for your pup because Chesapeake Bay has 824 properties that roll out the welcome mat to doggie guests. Let your four-legged buddy join in on the family trip at one of our pet-friendly vacation rentals on Vrbo. Simply enter your destination and dates, then check the “Pets allowed” filter box.
Are there large group vacation rentals in Chesapeake Bay?
Chesapeake Bay has 1,215 vacation rentals that can cater to 10 or more people. These properties come with plenty of space to share good times with friends and family.
What are the top attractions for families in Chesapeake Bay?
There are plenty of amazing things to see and do with the family in Chesapeake Bay, such as:

  • Virginia Beach Boardwalk
  • National Mall
  • White House

Are there one-bedroom vacation rentals in Chesapeake Bay?
Yes, Chesapeake Bay has 2,081 one-bedroom rentals available. Often located in sought-after areas thanks to their smaller size, a one-bedroom vacation rental is great if you’re getting away with your partner or a buddy. And with plenty of home comforts like kitchens and more privacy, you’ll be able to kick back and relax while sightseeing around this incredible destination.
Can I find two-bedroom vacation rentals in Chesapeake Bay?
Gather your nearest and dearest and enjoy a relaxing escape in one of the 2,163 two-bedroom vacation rentals Chesapeake Bay has to offer.
Are there vacation rentals with WiFi in Chesapeake Bay?
Whether you want to keep up to date with the news, look over emails or update your social media, there are 3,011 vacation homes with WiFi in Chesapeake Bay. Check the “WiFi” box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Chesapeake Bay?
Chesapeake Bay has 6,968 vacation rentals where you’ll be able to wind down in air-conditioned comfort. To find a property on Vrbo that features this amenity, choose your travel dates and use the handy filters to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Chesapeake Bay?
The minimum age permitted can vary across properties on Vrbo, so be sure to look at the rules of the vacation home in Chesapeake Bay you want to book. But typically, it’s 16, 18 or 21.
How long can I rent a vacation rental in Chesapeake Bay for?
The length of time you can rent a vacation rental in Chesapeake Bay differs according to the property. Just enter your desired travel dates to display a list of options offering extended stays. With tons of amenities such as full kitchens and air conditioning, as well as some offering weekly or monthly discounts, you’re sure to discover a terrific place to call your home away from home in Chesapeake Bay.
Does Vrbo offer discounts for vacation homes in Chesapeake Bay?
Overnight trip or extended vacation, Vrbo has some bargain deals and special discounts in Chesapeake Bay to match your style and budget. Take a look at our weekly and monthly discounts on vacation rentals, or see what’s just been added with one of our newly listed homes. Whatever kind of getaway you’re after, you’ll find the ideal place to stay — without breaking the bank.

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