Book Holiday Homes in Eastern Shore of Virginia

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Featured Holiday Homes in Eastern Shore of Virginia

Blufin Bungalows & Marina

Blufin Bungalows & Marina

3 out of 5
2477 Main St Chincoteague VA
With a stay at Blufin Bungalows & Marina in Chincoteague (Down the Marsh), you'll be a 2-minute drive from Chincoteague Channel and 6 minutes from Robert N. ...
Opens in a new windowBlufin Bungalows & Marina
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!
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Tranquil Shores - Relaxation With a Water View!

Tranquil Shores - Relaxation With a Water View!

Chincoteague VA
Located in Chincoteague, this vacation home is by the sea, within a 5-minute drive of Maui Jack's Waterpark and Chincoteague Channel.
Opens in a new windowTranquil Shores - Relaxation With a Water View!
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$609 per night from 17 Dec to 18 Dec
AU$609
17 Dec - 18 Dec
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
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$436 per night from 15 Jan to 16 Jan
AU$436
15 Jan - 16 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
Sweet cottage with outdoor shower

Sweet cottage with outdoor shower

Chincoteague VA
With a stay at this vacation home in Chincoteague, you'll be within a 5-minute drive of Robert N. Reed Downtown Waterfront Park and Maui Jack's Waterpark.
Opens in a new windowSweet cottage with outdoor shower
Saltwater Pony on Chincoteague Island!

Saltwater Pony on Chincoteague Island!

Chincoteague Island VA
Located in Chincoteague (Snotty Ridge), this vacation home is within a 5-minute drive of Chincoteague Channel and Robert N. Reed Downtown Waterfront Park.
Opens in a new windowSaltwater Pony on Chincoteague Island!
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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.

Eastern Shore of Virginia 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 Eastern Shore of Virginia vacation homes are the perfect way for you to wing it.

Holiday houses in Eastern Shore of Virginia 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 Eastern Shore of Virginia 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 Eastern Shore of Virginia adventures, obvs.

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

Eastern Shore of Virginia Holiday Homes essential information

Accommodation
919 Holiday Homes
Lowest Price
AU$139
Highest Price
AU$609
Popular accommodation
Blufin Bungalows & Marina, 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!, Tranquil Shores - Relaxation With a Water View!, 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, Sweet cottage with outdoor shower, Saltwater Pony on Chincoteague Island!

Top trending hotels in Eastern Shore of Virginia

Key West Cottages

Key West Cottages

3 out of 5
4251 Main Street Chincoteague VA
With a stay at Key West Cottages in Chincoteague (Downtown Chincoteague), you'll be within a 10-minute walk of Chincoteague Channel and Robert N. Reed Downtown ...
Opens in a new windowKey West Cottages
Refuge Inn

Refuge Inn

3 out of 5
7058 Maddox Blvd. Chincoteague VA
The price is AU$165 per night from 22 Dec to 23 Dec
AU$165
22 Dec - 23 Dec
includes taxes & fees
With a stay at Refuge Inn in Chincoteague, you'll be 0.6 mi (1 km) from Chincoteague National Wildlife Refuge and 10.4 mi (16.7 km) from Wallops Flight ...
Opens in a new windowRefuge Inn
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$139 per night from 22 Dec to 23 Dec
AU$139
22 Dec - 23 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
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Waterside Inn

Waterside Inn

2 out of 5
3761 Main St Chincoteague VA
Located in Chincoteague (Downtown Chincoteague), Waterside Inn is within a 5-minute drive of Robert N. Reed Downtown Waterfront Park and Chincoteague ...
Opens in a new windowWaterside Inn
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See all available properties in Eastern Shore of Virginia
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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.