24659+ Rental Villas and Private Getaways in Chesapeake Bay |
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Chesapeake Bay Villa Rentals

About Chesapeake Bay Vacation Rentals

There are more than 24659 incredible getaway rentals that are available in Chesapeake Bay. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Chesapeake Bay.

BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Chesapeake Bay, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Chesapeake Bay. Places to stay near Chesapeake Bay are 747.03 ft² on average, with prices averaging GB £247 a night.

BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Chesapeake Bay. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.

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Top Private Villas, Resorts, and Rentals in Chesapeake Bay

Type Count
Vacation Homes 10507
Holiday Apartments 6824
Cottages 570
B&B 357
Villas 254
Others 95
Cabin Rentals 85
Unique Vacation Rentals 45
Unique Vacation Rentals 12
Ski Chalet Rentals 5

Use these Quick Filters to Find a Vacation Rental in Chesapeake Bay

★ Pro Tip: BedroomVillas is a luxury vacation rental website, pulling some of the top private villas and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible beach houses and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Chesapeake Bay with BedroomVillas.

Weather in Chesapeake Bay, US

View the weather forecast for Chesapeake Bay before booking your Chesapeake Bay Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Stay Near Chesapeake Bay's Top Attractions

A Large Selection of Villas and Vacation Rentals from Around the World Chesapeake Bay's Research Top Attractions For Your Vacation


White House
Busch Gardens Williamsburg
National Mall
Virginia Beach Boardwalk
Washington Monument
National Aquarium in Baltimore
Colonial Williamsburg
Walter E. Washington Convention Center
George Washington University
Arlington National Cemetery
Smithsonian National Air and Space Museum
Naval Station Norfolk
Lincoln Memorial
Baltimore Cruise Terminal
University of Maryland-College Park
Johns Hopkins University
Capital One Arena
United States Capitol
Baltimore Convention Center
National Museum of Natural History

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Maryland 17,396 Properties
Northern Chesapeake Bay 10,228 Properties
Washington 3,370 Properties
Norfolk - Virginia Beach 3,266 Properties
District of Columbia 3,261 Properties
Virginia Beach 2,130 Properties
Northwest 2,009 Properties
Baltimore 1,581 Properties
Anne Arundel County 1,522 Properties
Northeast Virginia Beach 1,232 Properties
James City County 1,179 Properties
Williamsburg 1,176 Properties

Complexes around Chesapeake Bay, US


Wyndham Patriots Lockoff Williamsburg 172 Properties
Phoenixpark Washington 22 Properties
Alexandria 52 Properties
Virginia Beach Oceanfrnt 94 Properties
Wyndham National Harbor 59 Properties
Inn 18 Properties
Ballston 47 Properties
Enjoy Beauty The Chesapeake Bay 40 Properties
Bethesda 33 Properties
Georgetown 29 Properties
Crystal City Arlington Va 7 Properties
Dupont Circle Nr U Street Metro Glen Mkt 12 Properties
Capitol Hill 16 Properties
Pentagon City 12 Properties
Prince George St Annapolis 6 Properties
See More Complexes

Frequently Asked Questions About Chesapeake Bay?

What are the top hotels or resorts in Chesapeake Bay?

We provide an array of great vacation destinations in Chesapeake Bay. If you are looking to stay in or around the Chesapeake Bay area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Chesapeake Bay:

How many vacation rentals have private pools in Chesapeake Bay?

We have 1312 luxury villas and vacation rentals featuriung a private pool in and near Chesapeake Bay. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel or resort in Chesapeake Bay is best for families?

Searching for a family-friendly getaway in Chesapeake Bay? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Chesapeake Bay?

BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2025 is over 24659 in the Chesapeake Bay area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Chesapeake Bay. 

Nearby Neighborhood (16) 
Neighborhood Property Count
Northwest Rental Villas and Private Getaways in Chesapeake Bay, US 2009
Northeast Virginia Beach Rental Villas and Private Getaways in Chesapeake Bay, US 1232
Northeast Rental Villas and Private Getaways in Chesapeake Bay, US 743
Downtown Washington D.C. Rental Villas and Private Getaways in Chesapeake Bay, US 674
Capitol Hill Rental Villas and Private Getaways in Chesapeake Bay, US 609
Downtown Baltimore Rental Villas and Private Getaways in Chesapeake Bay, US 599
Crystal City Rental Villas and Private Getaways in Chesapeake Bay, US 244
Rosslyn Rental Villas and Private Getaways in Chesapeake Bay, US 204
Dupont Circle Rental Villas and Private Getaways in Chesapeake Bay, US 195
Downtown Rental Villas and Private Getaways in Chesapeake Bay, US 148
Old Town Alexandria Rental Villas and Private Getaways in Chesapeake Bay, US 111
Fells Point Rental Villas and Private Getaways in Chesapeake Bay, US 71
Georgetown Rental Villas and Private Getaways in Chesapeake Bay, US 63
Foggy Bottom Rental Villas and Private Getaways in Chesapeake Bay, US 53
Inner Harbor Rental Villas and Private Getaways in Chesapeake Bay, US 44
Pentagon City Rental Villas and Private Getaways in Chesapeake Bay, US 42

People Also Ask

There are 2703 hotels in Chesapeake Bay 725 resorts, and 17670 rentals

Recently Booked Hotels, Resorts, or Rentals in Chesapeake Bay