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
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
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

Ridge
With a stay at this vacation home in Ridge (Point Lookout), you'll be within a 10-minute drive of Cardinal Gibbons Park and First District Community Park.
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
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
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Private, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!

Private, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!

Reedville
Located in Reedville, this vacation home is by the sea, within a 15-minute drive of Reedville Historic District and Reedville Fishermen's Museum.
Private, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!
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
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
July 4th available! Waterfront getaway! Fish and crab from private dock!

July 4th available! Waterfront getaway! Fish and crab from private dock!

Reedville
A stay at this vacation home places you in the heart of Reedville, a 5-minute drive from Buzzard's Point Marina and 7 minutes from Reedville Fishermen's ...
July 4th available! Waterfront getaway! Fish and crab from private dock!
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 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.)
Waterfront Getaway: Kayaks, Paddle Board, Fishing!

Waterfront Getaway: Kayaks, Paddle Board, Fishing!

Reedville
Located in Reedville, this vacation home is on the waterfront, within a 10-minute drive of Reedville Fishermen's Museum and Buzzard's Point Marina.
Waterfront Getaway: Kayaks, Paddle Board, Fishing!
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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
Highest Price
Popular accommodation
Cottage near the Bay, **FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**, Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10, Private, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!, Get away to relax on Smith Island in the Chesapeake Bay with golf cart included , July 4th available! Waterfront getaway! Fish and crab from private dock!, Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront! , Bay House with Amazing View & Swimming Pool (open May- Sept.), Waterfront Getaway: Kayaks, Paddle Board, Fishing!

Top trending hotels in Smith Island

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
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
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
Save an average of 15% on thousands of hotels when you're signed in
Blue Heron Cottage On Smith's Island

Blue Heron Cottage On Smith's Island

Smith Island
When you stay at this cottage in Smith Island, you'll be on the waterfront and convenient to Tylerton County Dock and Smith Island.
Blue Heron Cottage On Smith's Island
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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.

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^Subject to availability and chosen travel dates.