Book Holiday Homes in Smith Island

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Featured Holiday Homes in Smith Island

Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

2 out of 5
Deal Island Historic District
Located in Deal Island, this vacation home is a 4-minute drive from Shark Fin Shoal and 7 minutes from Rock Island.
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

Ridge
With a stay at this vacation home in Ridge (Point Lookout), you'll be within a 10-minute drive of Confederate Memorial Park and Cardinal Gibbons Park.
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
Private Northern Neck Retreat on Chesapeake Bay and Taskmaker Creek.

Private Northern Neck Retreat on Chesapeake Bay and Taskmaker Creek.

Reedville
Located in Reedville, this vacation home is on a river, within a 10-minute drive of Reedville Fishermen's Museum and Reedville Historic District.
Private Northern Neck Retreat on Chesapeake Bay and Taskmaker Creek.
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Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier

Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier

Heathsville
Located in Ophelia, this vacation home is on the waterfront, within a 15-minute drive of Ginny Beach and Northern Neck Farm Museum.
Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier
When you want to get away from everything Magnolia shores 2 acres of tranquility

When you want to get away from everything Magnolia shores 2 acres of tranquility

Reedville
Located in Reedville, this vacation home is on the waterfront, within a 15-minute drive of Reedville Historic District and Reedville Fishermen's Museum.
When you want to get away from everything Magnolia shores 2 acres of tranquility
Bay House with Amazing View & Swimming Pool (open May- Sept.)

Bay House with Amazing View & Swimming Pool (open May- Sept.)

Reedville
Located in Reedville, this vacation home is on the waterfront, within a 5-minute drive of Reedville Fishermen's Museum and Reedville Historic District.
Bay House with Amazing View & Swimming Pool (open May- Sept.)
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10

Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10

Heathsville
Located in Heathsville, this vacation home is on the waterfront, within a 15-minute drive of Ginny Beach and Smith Point Marina.
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
Bay Estate by AvantStay | Waterfront, Private Pond

Bay Estate by AvantStay | Waterfront, Private Pond

Dameron
Located in Dameron, this vacation home is by the ocean, within a 15-minute drive of Saint Jerome Beach and Cardinal Gibbons Park.
Bay Estate by AvantStay | Waterfront, Private Pond
Virginia Retreat on Wicomico River w/ Dock!

Virginia Retreat on Wicomico River w/ Dock!

Burgess
Located in Burgess, this vacation home is on the waterfront, within a 15-minute drive of Northern Neck Farm Museum and Reedville Fishermen's Museum.
Virginia Retreat on Wicomico River w/ Dock!
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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.

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

Holiday houses in Smith Island 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 Smith Island 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 Smith Island adventures, obvs.

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

Smith Island Holiday Homes essential information

Accommodation
79 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD, Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks, Private Northern Neck Retreat on Chesapeake Bay and Taskmaker Creek. , Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier, When you want to get away from everything Magnolia shores 2 acres of tranquility, Bay House with Amazing View & Swimming Pool (open May- Sept.), Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10, Bay Estate by AvantStay | Waterfront, Private Pond, Virginia Retreat on Wicomico River w/ Dock!

Top trending hotels in Smith Island

Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!

Smith Island
When you stay at this vacation home in Smith Island, you'll be on the waterfront and 11 minutes by foot from Terrapin Sand Point.
Historic home on Smith Island w/ dock!
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

Smith Island
When you stay at this cottage in Smith Island, you'll be on the waterfront and steps from Terrapin Sand Point.
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage

Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage

Smith Island
When you stay at this vacation home in Smith Island, you'll be steps from Terrapin Sand Point.
Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage
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Pet-Friendly Smith Island Cottage w/ Golf Cart!

Pet-Friendly Smith Island Cottage w/ Golf Cart!

Ewell
When you stay at this cottage in Smith Island, you'll be near the beach and steps from Terrapin Sand Point.
Pet-Friendly Smith Island Cottage w/ Golf Cart!
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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.