Book Holiday Homes in Smith Island

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Featured Holiday Homes in Smith Island

Cottage near the Bay

Cottage near the Bay

Crisfield
The price is AU$292 per night from 17 Aug to 18 Aug
AU$292
17 Aug - 18 Aug
includes taxes & fees
With a stay at this vacation home in Crisfield, you'll be within a 5-minute drive of Crisfield Public Library and Edward W. McCready Memorial Hospital.
Cottage near the Bay
Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!

Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!

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.
Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!
Bay Front Small Contemporary

Bay Front Small Contemporary

Reedville
Located in Reedville, this vacation home is on the waterfront, within a 10-minute drive of Reedville Fishermen's Museum and Reedville Historic District.
Bay Front Small Contemporary
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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!
Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

Smith Island
The price is AU$534 per night from 26 Aug to 27 Aug
AU$534
26 Aug - 27 Aug
includes taxes & fees
When you stay at this vacation home in Smith Island, you'll be 3 minutes by foot from Terrapin Sand Point.
Get away to relax on Smith Island in the Chesapeake Bay with golf cart included
Secluded River Front Cottage

Secluded River Front Cottage

Scotland
Located in Scotland (Point Lookout), this vacation home is within a 5-minute drive of Point Lookout State Park and Lake Conoy.
Secluded River Front Cottage
Beautiful Bayfront with Sanctuary Private Beach

Beautiful Bayfront with Sanctuary Private Beach

Saxis
With a stay at this vacation home in Saxis, you'll be 16 mi (25.7 km) from Virginia Welcome Center at New Church and 16.1 mi (25.9 km) from Bloxom Winery.
Beautiful Bayfront with Sanctuary Private Beach
Private 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed

Private 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed

Reedville
Located in Reedville, this vacation home is on the waterfront, a 3-minute drive from Fleeton Beach and 6 minutes from Reedville Fishermen's Museum.
Private 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed
Walk to Main Street: Family-Friendly Crisfield Gem

Walk to Main Street: Family-Friendly Crisfield Gem

Crisfield
With a stay at this vacation home in Crisfield, you'll be within a 5-minute drive of Gov. Tawes Library and Crisfield Municipal Park.
Walk to Main Street: Family-Friendly Crisfield Gem
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See all available properties in Smith 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.

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
90 Holiday Homes
Lowest Price
AU$292
Highest Price
AU$534
Popular accommodation
Cottage near the Bay, Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront! , Bay Front Small Contemporary, Historic home on Smith Island w/ dock!, Get away to relax on Smith Island in the Chesapeake Bay with golf cart included , Secluded River Front Cottage, Beautiful Bayfront with Sanctuary Private Beach , Private 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed, Walk to Main Street: Family-Friendly Crisfield Gem

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!
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!
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
Save an average of 15% on thousands of hotels when you're signed in
Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

Smith Island
The price is AU$534 per night from 26 Aug to 27 Aug
AU$534
26 Aug - 27 Aug
includes taxes & fees
When you stay at this vacation home in Smith Island, you'll be 3 minutes by foot from Terrapin Sand Point.
Get away to relax on Smith Island in the Chesapeake Bay with golf cart included
Don't see what you're looking for?
See all available properties in Smith Island
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.

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^Subject to availability and chosen travel dates.