Book Holiday Homes in Chesapeake
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Featured Holiday Homes in Chesapeake

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

Brand NEW POOL for 2025~Oceanfront Home “Sea Watch”~REDUCED RATES APRIL AND MAY~

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

Spacious oceanfront house w/beach access, decks, grill & free WIFI

Dog-friendly home with private pool, fenced yard, ocean view, nice deck & WiFi

The Art Door only minutes from beach

Oceanside beach home private outdoor pool, fast WiFi & W/D - dog-friendly

Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Chesapeake 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 vacation homes are the perfect way for you to wing it.
Holiday houses in Chesapeake 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 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 adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chesapeake 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 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 Holiday Homes essential information
Accommodation | 1439 Holiday Homes |
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Lowest Price | AU$174 |
Highest Price | AU$652 |
Popular accommodation | Your own private beach with this charming 3-bedroom beachfront house!, Brand NEW POOL for 2025~Oceanfront Home “Sea Watch”~REDUCED RATES APRIL AND MAY~, Super close to beaches, the historic triangle, and bush gardens!, Spacious oceanfront house w/beach access, decks, grill & free WIFI, Dog-friendly home with private pool, fenced yard, ocean view, nice deck & WiFi, The Art Door only minutes from beach, Oceanside beach home private outdoor pool, fast WiFi & W/D - dog-friendly, Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required., Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home |
Holiday Homes in Chesapeake
Top Locations for Holiday Homes in Chesapeake
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Holiday Inn Express Chesapeake - Norfolk by IHG

Wingate by Wyndham Chesapeake

TRU by Hilton Chesapeake, VA

Hyatt Place Virginia Beach / Oceanfront
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^Subject to availability and chosen travel dates.