Book Holiday Homes in Machipongo

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Machipongo

Cape Charles Newly Updated Family-friendly Beach House, 1 Block to Private Beach

Cape Charles Newly Updated Family-friendly Beach House, 1 Block to Private Beach

Cape Charles
Stay at this vacation home in Cape Charles. Enjoy balconies, in-room jetted tubs, and an in-room coffeemaker. Popular attractions Cape Charles Museum & Welcome ...
Cape Charles Newly Updated Family-friendly Beach House, 1 Block to Private Beach
Lil' Miss Clementine 2-bedroom home in Historic District with Golfcart option

Lil' Miss Clementine 2-bedroom home in Historic District with Golfcart option

2 out of 5
Cape Charles
Stay at this vacation home in Cape Charles. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Cape Charles Museum & Welcome Center and ...
Lil' Miss Clementine 2-bedroom home in Historic District with Golfcart option
Oyster Shack - true gem in heart of downtown!

Oyster Shack - true gem in heart of downtown!

2 out of 5
Cape Charles
Stay at this vacation home in Cape Charles. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Cape Charles Museum & Welcome Center ...
Oyster Shack - true gem in heart of downtown!
Save an average of 15% on thousands of hotels when you're signed in
Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks

Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks

Machipongo
Stay at this vacation home in Machipongo. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Chatham Vineyards and South Island are located ...
Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks
The Strand: Free Golf Carts, Paddle Boards, Tennis & Pool, 1 Blk to Beach

The Strand: Free Golf Carts, Paddle Boards, Tennis & Pool, 1 Blk to Beach

Cape Charles
The price is NZ$1,755 per night from 1 Jan to 2 Jan
NZ$1,755
includes taxes & fees
1 Jan - 2 Jan 2025
Book a stay at this family-friendly vacation home in Cape Charles. Enjoy free WiFi, tennis courts, and a pool table. Popular attractions Cape Charles Museum ...
The Strand: Free Golf Carts, Paddle Boards, Tennis & Pool, 1 Blk to Beach
Sunset Shores | Chesapeake Properties

Sunset Shores | Chesapeake Properties

Cape Charles
Book a stay at this beach vacation home in Cape Charles. Enjoy private pools, a beach locale, and a garden. Popular attractions Cape Charles Beach and Cape Charles ...
Sunset Shores | Chesapeake Properties
Nassawadox Creek Waterfront Home with Private Pool

Nassawadox Creek Waterfront Home with Private Pool

Exmore
Stay at this vacation home in Exmore. Enjoy free WiFi, private pools, and a garden. Popular attractions Horse Island and South Island are located nearby.
Nassawadox Creek Waterfront Home with Private Pool
Sisters 3 by the Sea, 400 Feet To The Beach

Sisters 3 by the Sea, 400 Feet To The Beach

Cape Charles
Stay at this vacation home in Cape Charles. Enjoy free WiFi, a garden, and patios. Popular attractions Cape Charles Beach and Cape Charles Museum & Welcome Center ...
Sisters 3 by the Sea, 400 Feet To The Beach
Minutes to the BEACH! Large yard w/fire pit,  bocci, ample parking and fun!

Minutes to the BEACH! Large yard w/fire pit, bocci, ample parking and fun!

Cape Charles
Stay at this vacation home in Cape Charles. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Cape Charles Museum & Welcome Center and Bay ...
Minutes to the BEACH! Large yard w/fire pit, bocci, ample parking and fun!
Don't see what you're looking for?
See all available properties in Machipongo
View all properties
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
247 Holiday Homes
Lowest Price
NZ$159
Highest Price
NZ$1,755
Popular accommodation
Cape Charles Newly Updated Family-friendly Beach House, 1 Block to Private Beach, Lil' Miss Clementine 2-bedroom home in Historic District with Golfcart option, Oyster Shack - true gem in heart of downtown!, Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks, The Strand: Free Golf Carts, Paddle Boards, Tennis & Pool, 1 Blk to Beach, Sunset Shores | Chesapeake Properties, Nassawadox Creek Waterfront Home with Private Pool, Sisters 3 by the Sea, 400 Feet To The Beach, Minutes to the BEACH! Large yard w/fire pit, bocci, ample parking and fun!

Top trending hotels in Machipongo

Shore Stay Suites

Shore Stay Suites

2 out of 5
26406 Lankford Hwy, Cape Charles, VA
Fully refundableReserve now, pay when you stay
The price is NZ$215 per night from 26 Dec to 27 Dec
NZ$215
includes taxes & fees
26 Dec - 27 Dec
Stay at this hotel in Cape Charles. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions ...
Shore Stay Suites
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 NZ$187 per night from 3 Jan to 4 Jan
NZ$187
includes taxes & fees
3 Jan - 4 Jan 2025
Stay at this hotel in Exmore. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Hampton Inn & Suites Exmore - Eastern Shore
Holiday Inn Express and Suites Exmore, Eastern Shore, an IHG Hotel

Holiday Inn Express and Suites Exmore, Eastern Shore, an IHG Hotel

2.5 out of 5
3446 Lankford Hwy, Exmore, VA
Fully refundable
The price is NZ$171 per night from 17 Jan to 18 Jan
NZ$171
includes taxes & fees
17 Jan - 18 Jan 2025
Book a stay at this business-friendly hotel in Exmore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Holiday Inn Express and Suites Exmore, Eastern Shore, an IHG Hotel
Save an average of 15% on thousands of hotels when you're signed in
Quality Inn & Suites

Quality Inn & Suites

2.5 out of 5
2543 Lankford Hwy, Exmore, VA
Fully refundableReserve now, pay when you stay
The price is NZ$159 per night from 30 Dec to 31 Dec
NZ$159
includes taxes & fees
30 Dec - 31 Dec
Book a stay at this business-friendly hotel in Exmore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Quality Inn & Suites
Don't see what you're looking for?
See all available properties in Machipongo
View all properties
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.