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
When you stay at Blufin Bungalows & Marina in Chincoteague, you'll be on the beach and 13 minutes by foot from Chincoteague Channel.
Blufin Bungalows & Marina
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
Located in Cape Charles, this vacation home is within a 5-minute drive of Cape Charles Museum & Welcome Center and Cape Charles Beach.
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
With a stay at this vacation home, you'll be centrally located in Cape Charles, just a 4-minute walk from Cape Charles Museum & Welcome Center and 13 minutes ...
Lil' Miss Clementine 2-bedroom home in Historic District with Golfcart option
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Oyster Shack - true gem in heart of downtown!

Oyster Shack - true gem in heart of downtown!

2 out of 5
Cape Charles
When you stay at this vacation home in Cape Charles, you'll be near the beach, within a 15-minute walk of Cape Charles Museum & Welcome Center and Cape Charles ...
Oyster Shack - true gem in heart of downtown!
Duck's Delight - Pet friendly rentals within walking distance to Maddox Blvd!

Duck's Delight - Pet friendly rentals within walking distance to Maddox Blvd!

Chincoteague Island
Located in Chincoteague, this vacation home is within a 15-minute walk of Robert N. Reed Downtown Waterfront Park and Chincoteague Channel.
Duck's Delight - Pet friendly rentals within walking distance to Maddox Blvd!
Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks

Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks

Machipongo
With a stay at this vacation home in Machipongo, you'll be within a 15-minute drive of Chatham Vineyards and Barrier Islands Center.
Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks
Cozy Nest - Waterview, Pet Friendly, Screened Porch

Cozy Nest - Waterview, Pet Friendly, Screened Porch

Chincoteague Island
With a stay at this vacation home in Chincoteague, you'll be a 3-minute walk from Captain Timothy Hill House and within a 5-minute drive of Chincoteague ...
Cozy Nest - Waterview, Pet Friendly, Screened Porch
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 AU$1,605 per night from 1 Jan to 2 Jan
AU$1,605
includes taxes & fees
1 Jan - 2 Jan 2025
When you stay at this vacation home in Cape Charles, you'll be near the beach, within a 5-minute drive of Cape Charles Museum & Welcome Center and Cape Charles ...
The Strand: Free Golf Carts, Paddle Boards, Tennis & Pool, 1 Blk to Beach
Sunset Shores | Chesapeake Properties

Sunset Shores | Chesapeake Properties

Cape Charles
With a stay at this vacation home in Cape Charles, you'll be on the beach, a 4-minute walk from Cape Charles Beach and a 2-minute drive from Cape Charles Museum ...
Sunset Shores | Chesapeake Properties
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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
760 Holiday Homes
Lowest Price
AU$106
Highest Price
AU$1,605
Popular accommodation
Blufin Bungalows & Marina, 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!, Duck's Delight - Pet friendly rentals within walking distance to Maddox Blvd!, Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks, Cozy Nest - Waterview, Pet Friendly, Screened Porch, The Strand: Free Golf Carts, Paddle Boards, Tennis & Pool, 1 Blk to Beach, Sunset Shores | Chesapeake Properties

Top trending hotels in Eastern Shore of Virginia

Key West Cottages

Key West Cottages

3 out of 5
4251 Main Street, Chincoteague, VA
The price is AU$217 per night from 5 Jan to 6 Jan
AU$217
includes taxes & fees
5 Jan - 6 Jan 2025
When you stay at Key West Cottages in Chincoteague, you'll be on the waterfront, within a 10-minute walk of Chincoteague Channel and Robert N. Reed Downtown ...
Key West Cottages
Refuge Inn

Refuge Inn

3 out of 5
7058 Maddox Blvd., Chincoteague, VA
Fully refundableReserve now, pay when you stay
The price is AU$177 per night from 26 Dec to 27 Dec
AU$177
includes taxes & fees
26 Dec - 27 Dec
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 ...
Refuge Inn
Waterside Inn

Waterside Inn

2 out of 5
3761 Main St, Chincoteague, VA
Fully refundableReserve now, pay when you stay
The price is AU$106 per night from 26 Dec to 27 Dec
AU$106
includes taxes & fees
26 Dec - 27 Dec
Located in Chincoteague, Waterside Inn is by the ocean, within a 5-minute drive of Robert N. Reed Downtown Waterfront Park and Chincoteague Channel.
Waterside Inn
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Comfort Suites Chincoteague Island Bayfront Resort

Comfort Suites Chincoteague Island Bayfront Resort

2.5 out of 5
4195 Main St, Chincoteague, VA
Fully refundableReserve now, pay when you stay
The price is AU$178 per night from 5 Jan to 6 Jan
AU$178
includes taxes & fees
5 Jan - 6 Jan 2025
Located in Chincoteague, Comfort Suites Chincoteague Island Bayfront Resort is on the boardwalk/promenade, just a 4-minute walk from Robert N. Reed Downtown ...
Comfort Suites Chincoteague Island Bayfront Resort
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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.