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!

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 Norfolk State University.
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~

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

2 out of 5
Virginia Beach
With a stay at this vacation home in Virginia Beach (Sandbridge), you'll be steps from Sandbridge Beach and a 4-minute drive from False Cape Beach.
Brand NEW POOL for 2025~Oceanfront Home “Sea Watch”~REDUCED RATES APRIL AND MAY~
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!
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Spacious oceanfront house w/beach access, decks, grill & free WIFI

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

Virginia Beach
With a stay at this vacation home in Virginia Beach (Sandbridge), you'll be steps from Sandbridge Beach and a 5-minute drive from False Cape Beach.
Spacious oceanfront house w/beach access, decks, grill & free WIFI
Dog-friendly home with private pool, fenced yard, ocean view, nice deck & WiFi

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

Virginia Beach
With a stay at this vacation home in Virginia Beach (Sandbridge), you'll be a 2-minute drive from Sandbridge Beach and 7 minutes from False Cape Beach.
Dog-friendly home with private pool, fenced yard, ocean view, nice deck & WiFi
The Art Door only minutes from beach

The Art Door only minutes from beach

Virginia Beach
The price is AU$395 per night from 1 Apr to 2 Apr
AU$395
includes taxes & fees
1 Apr - 2 Apr
With a stay at this vacation home in Virginia Beach (Northeast Virginia Beach), you'll be within a 10-minute drive of Virginia Beach Boardwalk and Virginia Beach ...
The Art Door only minutes from beach
Oceanside beach home private outdoor pool, fast WiFi & W/D - dog-friendly

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

Virginia Beach
With a stay at this vacation home in Virginia Beach (Sandbridge), you'll be a 1-minute drive from Sandbridge Beach and 6 minutes from False Cape Beach.
Oceanside beach home private outdoor pool, fast WiFi & W/D - dog-friendly
Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.

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

Corolla
With a stay at this vacation home, you'll be centrally located in Corolla, within a 5-minute walk of Outer Banks Beaches and Swan Beach.
Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Portsmouth
The price is AU$652 per night from 1 Apr to 2 Apr
AU$652
includes taxes & fees
1 Apr - 2 Apr
With a stay at this vacation home, you'll be centrally located in Portsmouth, within a 10-minute drive of Waterside District and Norfolk State University.
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
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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 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
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

Top trending hotels in Chesapeake

Holiday Inn Express Chesapeake - Norfolk by IHG

Holiday Inn Express Chesapeake - Norfolk by IHG

2.5 out of 5
721 Conference Center Drive, Chesapeake, VA
Fully refundable
The price is AU$179 per night from 6 Apr to 7 Apr
AU$179
includes taxes & fees
6 Apr - 7 Apr
When you stay at Holiday Inn Express Chesapeake - Norfolk by IHG in Chesapeake, you'll be connected to the convention center, a 3-minute drive from Greenbrier ...
Holiday Inn Express Chesapeake - Norfolk by IHG
Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

2.5 out of 5
817 Greenbrier Circle, Chesapeake, VA
Fully refundableReserve now, pay when you stay
The price is AU$174 per night from 1 Apr to 2 Apr
AU$174
includes taxes & fees
1 Apr - 2 Apr
When you stay at Wingate by Wyndham Chesapeake in Chesapeake, you'll be in the business district, a 4-minute drive from Greenbrier Mall and 7 minutes from Regent ...
Wingate by Wyndham Chesapeake
TRU by Hilton Chesapeake, VA

TRU by Hilton Chesapeake, VA

2.5 out of 5
1570 CROSSWAYS BLVD, Chesapeake, VA
Fully refundableReserve now, pay when you stay
The price is AU$175 per night from 6 Apr to 7 Apr
AU$175
includes taxes & fees
6 Apr - 7 Apr
With a stay at TRU by Hilton Chesapeake, VA in Chesapeake (Greenbrier East), you'll be a 2-minute drive from Greenbrier Mall and 7 minutes from Regent ...
TRU by Hilton Chesapeake, VA
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Hyatt Place Virginia Beach / Oceanfront

Hyatt Place Virginia Beach / Oceanfront

3 out of 5
3601 ATLANTIC AVENUE, 36TH AND ATLANTIC, Virginia Beach, VA
Fully refundableReserve now, pay when you stay
The price is AU$223 per night from 6 Apr to 7 Apr
AU$223
includes taxes & fees
6 Apr - 7 Apr
With a stay at Hyatt Place Virginia Beach / Oceanfront in Virginia Beach (Northeast Virginia Beach), you'll be steps from Virginia Beach Boardwalk and Pacific ...
Hyatt Place Virginia Beach / Oceanfront
Don't see what you're looking for?
See all available properties in Chesapeake
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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.