Book Holiday Homes in Machipongo

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Featured Holiday Homes in Machipongo

The Crows Nest. <br>Sunsets at the Harbor. Enjoy bird’s eye view. Unique location!

The Crows Nest. <br>Sunsets at the Harbor. Enjoy bird’s eye view. Unique location!

Cape Charles VA
A stay at this vacation home places you in the heart of Cape Charles, steps from Chesapeake Bay and 13 minutes by foot from Central Park.
Opens in a new windowThe Crows Nest. <br>Sunsets at the Harbor. Enjoy bird’s eye view. Unique location!
A Perfect Location Next to Park and Walkable to Town and Beach. Pet Friendly!

A Perfect Location Next to Park and Walkable to Town and Beach. Pet Friendly!

Cape Charles VA
With a stay at this vacation home in Cape Charles (Historic Downtown Cape Charles), you'll be steps from Central Park and 9 minutes by foot from Chesapeake ...
Opens in a new windowA Perfect Location Next to Park and Walkable to Town and Beach. Pet Friendly!
1st Floor King Bed-Screened Porch-Family Friendly! Optional Resort & Golf Access

1st Floor King Bed-Screened Porch-Family Friendly! Optional Resort & Golf Access

Cape Charles VA
The price is AU$676 per night from 6 Jan to 7 Jan
AU$676
6 Jan - 7 Jan 2026
includes taxes & fees
With a stay at this vacation home in Cape Charles, you'll be a 4-minute walk from Bay Creek Golf Club and 9 minutes by foot from Chesapeake Bay.
Opens in a new window1st Floor King Bed-Screened Porch-Family Friendly! Optional Resort & Golf Access
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Downtown, Sleeps 9,  Dog-friendly, Short Walk to the Beach

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

Cape Charles VA
With a stay at this vacation home in Cape Charles (Historic Downtown Cape Charles), you'll be a 4-minute walk from Central Park and 6 minutes by foot from Cape ...
Opens in a new windowDowntown, Sleeps 9, Dog-friendly, Short Walk to the Beach
Salt Box, One Block to the Beach

Salt Box, One Block to the Beach

Cape Charles VA
The price is AU$454 per night from 4 Jan to 5 Jan
AU$454
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at this vacation home in Cape Charles (Historic Downtown Cape Charles), you'll be within a 5-minute walk of Central Park and Chesapeake Bay.
Opens in a new windowSalt Box, One Block to the Beach
Chesapeake Bay View

Chesapeake Bay View

Cape Charles VA
A stay at this vacation home places you in the heart of Cape Charles, within a 5-minute walk of Chesapeake Bay and Cape Charles Beach.
Opens in a new windowChesapeake Bay View
Coastal Bliss: 3500 sqft Beachfront Haven, Steps Away from Your Private Beach - Your Ultimate Cape Charles Getaway

Coastal Bliss: 3500 sqft Beachfront Haven, Steps Away from Your Private Beach - Your Ultimate Cape Charles Getaway

Cape Charles VA
With a stay at this vacation home in Cape Charles (Picketts Harbor), you'll be a 1-minute drive from Chesapeake Bay and 6 minutes from Kiptopeke State Park.
Opens in a new windowCoastal Bliss: 3500 sqft Beachfront Haven, Steps Away from Your Private Beach - Your Ultimate Cape Charles Getaway
Mid-century modern meets classic cape on the coast.

Mid-century modern meets classic cape on the coast.

Moon VA
When you stay at this vacation home in Westville, you'll be 10 minutes by car from Chesapeake Bay.
Opens in a new windowMid-century modern meets classic cape on the coast.
Bay cottage, Beach 100 yards away! RESERVE NOW!!!

Bay cottage, Beach 100 yards away! RESERVE NOW!!!

Cape Charles VA
The price is AU$721 per night from 24 Jan to 25 Jan
AU$721
24 Jan - 25 Jan 2026
includes taxes & fees
With a stay at this vacation home in Cape Charles (Historic Downtown Cape Charles), you'll be within a 5-minute walk of Chesapeake Bay and Cape Charles ...
Opens in a new windowBay cottage, Beach 100 yards away! RESERVE NOW!!!
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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.

Machipongo 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 Machipongo vacation homes are the perfect way for you to wing it.

Holiday houses in Machipongo 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 Machipongo 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 Machipongo adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Machipongo 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 Machipongo 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.

Machipongo Holiday Homes essential information

Accommodation
307 Holiday Homes
Lowest Price
AU$145
Highest Price
AU$721
Popular accommodation
The Crows Nest.
Sunsets at the Harbor. Enjoy bird’s eye view. Unique location!, A Perfect Location Next to Park and Walkable to Town and Beach. Pet Friendly!, 1st Floor King Bed-Screened Porch-Family Friendly! Optional Resort & Golf Access, Downtown, Sleeps 9, Dog-friendly, Short Walk to the Beach, Salt Box, One Block to the Beach, Chesapeake Bay View, Coastal Bliss: 3500 sqft Beachfront Haven, Steps Away from Your Private Beach - Your Ultimate Cape Charles Getaway, Mid-century modern meets classic cape on the coast. , Bay cottage, Beach 100 yards away! RESERVE NOW!!!

Top trending hotels in Machipongo

Holiday Inn Express & Suites Exmore - Eastern Shore by IHG

Holiday Inn Express & Suites Exmore - Eastern Shore by IHG

2.5 out of 5
3446 Lankford Hwy Exmore VA
Fully refundable
The price is AU$145 per night from 30 Dec to 31 Dec
AU$145
30 Dec - 31 Dec
includes taxes & fees
With a stay at Holiday Inn Express & Suites Exmore - Eastern Shore by IHG in Exmore, you'll be within a 15-minute walk of Northampton Shopping Center and Exmore ...
Opens in a new windowHoliday Inn Express & Suites Exmore - Eastern Shore by IHG
Hampton Inn & Suites Exmore - Eastern Shore

Hampton Inn & Suites Exmore - Eastern Shore

2.5 out of 5
4129 Lankford Hwy Exmore VA
Fully refundableReserve now, pay when you stay
The price is AU$149 per night from 9 Jan to 10 Jan
AU$149
9 Jan - 10 Jan 2026
includes taxes & fees
Located in Exmore, Hampton Inn & Suites Exmore - Eastern Shore is within a 5-minute drive of Northampton Shopping Center and Exmore Town Park.
Opens in a new windowHampton Inn & Suites Exmore - Eastern Shore
Shore Stay Suites

Shore Stay Suites

2 out of 5
26406 Lankford Hwy Cape Charles VA
Fully refundableReserve now, pay when you stay
When you stay at Shore Stay Suites in Cape Charles, you'll be within a 10-minute drive of John Custis' Tomb and Kiptopeke State Park.
Opens in a new windowShore Stay Suites
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Perfect Cozy Vacation Rental on the Eastern Shore

Perfect Cozy Vacation Rental on the Eastern Shore

Cape Charles VA
A stay at this condo places you in the heart of Cape Charles, a 4-minute drive from Cape Charles Museum & Welcome Center and 5 minutes from Central Park.
Opens in a new windowPerfect Cozy Vacation Rental on the Eastern Shore
Don't see what you're looking for?
See all available properties in Machipongo
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.