Book Holiday Homes in Chesapeake Bay

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Featured Holiday Homes in Chesapeake Bay

Blufin Bungalows & Marina

Blufin Bungalows & Marina

3 out of 5
2477 Main St, Chincoteague, VA
When you stay at Blufin Bungalows & Marina in Chincoteague, you'll be on the beach and 13 minutes by foot from Chincoteague Channel.
Blufin Bungalows & Marina
Spacious 4-bedroom townhome in brilliant Washington with WiFi, AC

Spacious 4-bedroom townhome in brilliant Washington with WiFi, AC

Washington
With a stay at this vacation home in Washington (Southeast), you'll be a 4-minute drive from Washington Navy Yard and 6 minutes from National Mall.
Spacious 4-bedroom townhome in brilliant Washington with WiFi, AC
Your own private beach with this charming 3-bedroom beachfront house!

Your own private beach with this charming 3-bedroom beachfront house!

Norfolk
With a stay at this vacation home in Norfolk (Cottage Line), you'll be within a 15-minute drive of Naval Station Norfolk and Hampton University.
Your own private beach with this charming 3-bedroom beachfront house!
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Bright, spacious house with private, scenic backyard in Arlington Forest

Bright, spacious house with private, scenic backyard in Arlington Forest

2 out of 5
Arlington
With a stay at this vacation home in Arlington (Arlington Forest), you'll be within a 10-minute drive of National Mall and Smithsonian Institution.
Bright, spacious house with private, scenic backyard in Arlington Forest
"Pura Vida" Fabulous 4 Bed Home near H St & Union Market

"Pura Vida" Fabulous 4 Bed Home near H St & Union Market

Washington
The price is AU$941 per night from 5 May to 6 May
AU$941
includes taxes & fees
5 May - 6 May
With a stay at this vacation home in Washington (Northeast), you'll be within a 5-minute drive of Union Station Shopping Center and Smithsonian Institution.
"Pura Vida" Fabulous 4 Bed Home near H St & Union Market
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Annapolis
A stay at this vacation home places you in the heart of Annapolis, steps from U.S. Naval Academy and Annapolis City Dock.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Super close to beaches, the historic triangle, and bush gardens!

Super close to beaches, the historic triangle, and bush gardens!

Hampton
Located in Hampton (Fox Hill), this vacation home is within a 10-minute drive of Hampton University and Buckroe Beach and Park.
Super close to beaches, the historic triangle, and bush gardens!
Charming 2-bedroom house in fantastic Takoma Park with WiFi, AC

Charming 2-bedroom house in fantastic Takoma Park with WiFi, AC

Takoma Park
With a stay at this vacation home in Takoma Park, you'll be within a 10-minute drive of Smithsonian's National Zoo and Howard University.
Charming 2-bedroom house in fantastic Takoma Park with WiFi, AC
Downtown, Sleeps 9,  Dog-friendly, Short Walk to the Beach

Downtown, Sleeps 9, Dog-friendly, Short Walk to the Beach

Cape Charles
With a stay at this vacation home in Cape Charles (Historic Downtown Cape Charles), you'll be within a 5-minute drive of Cape Charles Beach and Bay Creek Golf ...
Downtown, Sleeps 9, Dog-friendly, Short Walk to the Beach
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Chesapeake Bay Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chesapeake Bay vacation homes are the perfect way for you to wing it.

Holiday houses in Chesapeake Bay let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chesapeake Bay in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chesapeake Bay adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chesapeake Bay with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chesapeake Bay vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chesapeake Bay Holiday Homes essential information

Accommodation
602 Holiday Homes
Lowest Price
AU$224
Highest Price
AU$941
Popular accommodation
Blufin Bungalows & Marina, Spacious 4-bedroom townhome in brilliant Washington with WiFi, AC, Your own private beach with this charming 3-bedroom beachfront house!, Bright, spacious house with private, scenic backyard in Arlington Forest, "Pura Vida" Fabulous 4 Bed Home near H St & Union Market, Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Super close to beaches, the historic triangle, and bush gardens!, Charming 2-bedroom house in fantastic Takoma Park with WiFi, AC, Downtown, Sleeps 9, Dog-friendly, Short Walk to the Beach

Top trending hotels in Chesapeake Bay

Washington Plaza Hotel

Washington Plaza Hotel

4 out of 5
10 Thomas Circle NW, Washington, DC
Fully refundableReserve now, pay when you stay
The price is AU$253 per night from 2 May to 3 May
AU$253
includes taxes & fees
2 May - 3 May
A stay at Washington Plaza Hotel places you in the heart of Washington, within a 15-minute walk of Walter E. Washington Convention Center and White House.
Washington Plaza Hotel
Hilton Garden Inn Reagan National Airport

Hilton Garden Inn Reagan National Airport

3.5 out of 5
2020 Richmond Highway, Arlington, VA
Fully refundableReserve now, pay when you stay
The price is AU$224 per night from 10 May to 11 May
AU$224
includes taxes & fees
10 May - 11 May
With a stay at Hilton Garden Inn Reagan National Airport, you'll be centrally located in Arlington, within a 5-minute drive of National Museum of African American ...
Hilton Garden Inn Reagan National Airport
Omni Shoreham Hotel

Omni Shoreham Hotel

4 out of 5
2500 Calvert St Nw, Washington, DC
Fully refundableReserve now, pay when you stay
The price is AU$289 per night from 9 May to 10 May
AU$289
includes taxes & fees
9 May - 10 May
With a stay at Omni Shoreham Hotel in Washington (Northwest), you'll be 11 minutes by foot from Smithsonian's National Zoo.
Omni Shoreham Hotel
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State Plaza Hotel

State Plaza Hotel

3.5 out of 5
2116 E Street NW, Washington, DC
Fully refundableReserve now, pay when you stay
The price is AU$235 per night from 27 Apr to 28 Apr
AU$235
includes taxes & fees
27 Apr - 28 Apr
State Plaza Hotel is centrally located in Washington, a 3-minute walk from George Washington University and 7 minutes by foot from National Mall.
State Plaza Hotel
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.