Where to stay around Chesapeake Bay?

Our 2019 property listings offer a large selection of 2,900 vacation rentals near Chesapeake Bay. From 991 Houses to 796 Hotels, 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:

  • Virginia Beach: 1,619 vacation rentals
  • Pennsylvania: 7,740 vacation rentals
  • Virginia: 8,184 vacation rentals
  • Williamsburg: 497 vacation rentals
  • Annapolis: 532 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:

  • Virginia Beach: 1,619 rentals
  • Williamsburg: 497 rentals
  • Annapolis: 532 rentals
  • Cape Charles: 180 rentals
  • Saint Michaels: 162 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:

  • Baltimore-Washington International Thurgood Marshall Airport (BWI): 992 vacation rentals
  • Langley Afb (LFI): 236 vacation rentals
  • Salisbury Ocean City Wicomico Regional Airport (SBY): 57 vacation rentals

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

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.

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.

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.

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.

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.

Explore destinations around Chesapeake Bay

Virginia Beach
1,619 vacation rentals
Williamsburg
497 vacation rentals
Annapolis
532 vacation rentals
Cape Charles
180 vacation rentals
Saint Michaels
162 vacation rentals
Baltimore
365 vacation rentals
Colonial Beach
58 vacation rentals
Berkeley
435 vacation rentals
Norfolk
708 vacation rentals
Cambridge
197 vacation rentals
Chesapeake Beach
520 vacation rentals
Stevensville
632 vacation rentals
Easton
323 vacation rentals
Chestertown
71 vacation rentals
Hampton
2,290 vacation rentals
Crisfield
29 vacation rentals
Gloucester
114 vacation rentals
Onancock
31 vacation rentals
Royal Oak
96 vacation rentals
Rock Hall
40 vacation rentals