Book Holiday Homes in Smith Island

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Featured Holiday Homes in Smith Island

**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.
Opens in a new window**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
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.
Opens in a new windowPrivate infinity pool, plus your own dock, kayaks, and bikes on the waterfront!
Cottage near the Bay

Cottage near the Bay

Crisfield
The price is AU$288 per night from 1 Oct to 2 Oct
AU$288
1 Oct - 2 Oct
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.
Opens in a new windowCottage near the Bay
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Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!

Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!

Reedville
When you stay at this vacation home in Reedville, you'll be on the waterfront, within a 15-minute walk of Reedville Historic District and Reedville Fishermen's ...
Opens in a new windowSecluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!
Newly updated 3 bedroom cottage with Solo Stove fire pit

Newly updated 3 bedroom cottage with Solo Stove fire pit

Reedville
The price is AU$368 per night from 30 Sept to 1 Oct
AU$368
30 Sept - 1 Oct
includes taxes & fees
Located in Reedville, this vacation home is on a river, a 4-minute drive from Reedville Fishermen's Museum and 6 minutes from Reedville Historic District.
Opens in a new windowNewly updated 3 bedroom cottage with Solo Stove fire pit
Kentigern at Scotland Yards

Kentigern at Scotland Yards

Scotland
The price is AU$1,544 per night from 7 Oct to 8 Oct
AU$1,544
7 Oct - 8 Oct
includes taxes & fees
With a stay at this vacation home in Scotland (Point Lookout), you'll be a 2-minute drive from Confederate Memorial Park and 5 minutes from Lake Conoy.
Opens in a new windowKentigern at Scotland Yards
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.
Opens in a new windowHistoric home on Smith Island w/ dock!
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.
Opens in a new windowPrivate, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!
Summerlee at Scotland Yards

Summerlee at Scotland Yards

Scotland
With a stay at this vacation home in Scotland (Point Lookout), you'll be a 3-minute drive from Confederate Memorial Park and 6 minutes from Lake Conoy.
Opens in a new windowSummerlee at Scotland Yards
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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
84 Holiday Homes
Lowest Price
AU$147
Highest Price
AU$1,544
Popular accommodation
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**, Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront! , Cottage near the Bay, Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!, Newly updated 3 bedroom cottage with Solo Stove fire pit, Kentigern at Scotland Yards, Historic home on Smith Island w/ dock!, Private, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!, Summerlee at Scotland Yards

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.
Opens in a new windowHistoric home on Smith Island w/ dock!
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

Smith Island
The price is AU$535 per night from 30 Sept to 1 Oct
AU$535
30 Sept - 1 Oct
includes taxes & fees
When you stay at this vacation home in Smith Island, you'll be 3 minutes by foot from Terrapin Sand Point.
Opens in a new windowKayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart
Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island

Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island

Smith Island
When you stay at this vacation home in Smith Island, you'll be 3 minutes by foot from Terrapin Sand Point.
Opens in a new windowSpacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island
Save an average of 15% on thousands of hotels when you're signed in
Rodeway Inn at Somers Cove Marina

Rodeway Inn at Somers Cove Marina

2 out of 5
700 Norris Harbor Dr, Crisfield, MD
Fully refundableReserve now, pay when you stay
The price is AU$147 per night from 12 Oct to 13 Oct
AU$147
12 Oct - 13 Oct
includes taxes & fees
Located in Crisfield, Rodeway Inn at Somers Cove Marina is within a 5-minute drive of Somers Cove Marina and J. Millard Tawes Museum.
Opens in a new windowRodeway Inn at Somers Cove Marina
Don't see what you're looking for?
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.