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$310 per night from 25 Nov to 26 Nov
AU$310
includes taxes & fees
25 Nov - 26 Nov
With a stay at this vacation home in Crisfield, you'll be within a 5-minute drive of McCready Health Pavilion and J. Millard Tawes Museum.
Cottage near the Bay
Beachy Maryland A-Frame: Steps to Chesapeake Bay!

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

Scotland
Located in Scotland (Point Lookout), this vacation home is within a 5-minute drive of Confederate Memorial Park and Point Lookout State Park.
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

2 out of 5
Deal Island Historic District
When you stay at this vacation home in Deal Island, you'll be within a 5-minute drive of Shark Fin Shoal.
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!
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**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 Confederate Memorial Park and Point Lookout State Park.
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
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
Secluded, Waterfront Home: Huge Game Room, Private Dock, Pedal Boat, 4 Kayaks!

Secluded, Waterfront Home: Huge Game Room, Private Dock, Pedal Boat, 4 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 ...
Secluded, Waterfront Home: Huge Game Room, Private Dock, Pedal Boat, 4 Kayaks!
Waterfront Scotland Beach Retreat w/ Private Beach

Waterfront Scotland Beach Retreat w/ Private Beach

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 Point Lookout State Park.
Waterfront Scotland Beach Retreat w/ Private Beach
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!
18-Acre Waterfront Sanctuary: Peace & Privacy

18-Acre Waterfront Sanctuary: Peace & Privacy

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 Point Lookout State Park.
18-Acre Waterfront Sanctuary: Peace & Privacy
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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
75 Holiday Homes
Lowest Price
AU$310
Highest Price
AU$520
Popular accommodation
Cottage near the Bay, Beachy Maryland A-Frame: Steps to Chesapeake Bay!, Maryland Retreat: Walk to Bay, Beach & Boat Ramp!, **FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**, Beautiful Bayfront with Sanctuary Private Beach , Secluded, Waterfront Home: Huge Game Room, Private Dock, Pedal Boat, 4 Kayaks!, Waterfront Scotland Beach Retreat w/ Private Beach, Virginia Retreat on Wicomico River w/ Dock!, 18-Acre Waterfront Sanctuary: Peace & Privacy

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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Swanendele Inn at St. Mary's Maryland

Swanendele Inn at St. Mary's Maryland

5 out of 5
49946 Airedele Rd, Ridge, MD
The price is AU$520 per night from 24 Nov to 25 Nov
AU$520
includes taxes & fees
24 Nov - 25 Nov
Located in Ridge, Swanendele Inn at St. Mary's Maryland is in a rural location, within a 10-minute drive of Confederate Memorial Park and Point Lookout State ...
Swanendele Inn at St. Mary's Maryland
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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.