Book Holiday Homes in Smith Island

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Featured Holiday Homes in Smith Island

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

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

Reedville VA
With a stay at this vacation home in Reedville, you'll be on the waterfront, within a 10-minute drive of Chesapeake Bay and Reedville Fishermen's Museum.
Opens in a new windowSecluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!
FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS

FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS

Ridge MD
With a stay at this vacation home in Ridge (Point Lookout), you'll be within a 10-minute drive of Chesapeake Bay and Cardinal Gibbons Park.
Opens in a new windowFAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS
Cottage near the Bay

Cottage near the Bay

Crisfield MD
The price is AU$264 per night from 25 May to 26 May
AU$264
25 May - 26 May
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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Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10

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

Heathsville VA
Located in Heathsville, this vacation home is on the waterfront, within a 15-minute drive of Ginny Beach and Smith Point Marina.
Opens in a new windowMagical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
Steps to serene semi-private beach - Spring Getaway at "Bliss on the Bay"

Steps to serene semi-private beach - Spring Getaway at "Bliss on the Bay"

Scotland MD
With a stay at this vacation home in Scotland (Point Lookout), you'll be steps from Chesapeake Bay and 15 minutes by foot from Confederate Memorial Park.
Opens in a new windowSteps to serene semi-private beach - Spring Getaway at "Bliss on the Bay"
Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Scotland MD
With a stay at this vacation home in Scotland (Point Lookout), you'll be a 1-minute drive from Chesapeake Bay and 11 minutes from Confederate Memorial Park.
Opens in a new windowHideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay
Bay Front Small Contemporary

Bay Front Small Contemporary

Reedville VA
With a stay at this vacation home in Reedville, you'll be on the beach, within a 10-minute drive of Chesapeake Bay and Reedville Fishermen's Museum.
Opens in a new windowBay Front Small Contemporary
Private 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed

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

Reedville VA
With a stay at this vacation home in Reedville, you'll be on the waterfront, within a 5-minute drive of Chesapeake Bay and Fleeton Beach.
Opens in a new windowPrivate 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed
Private Dock and 200ft Shoreline w Panorama View

Private Dock and 200ft Shoreline w Panorama View

Heathsville VA
With a stay at this vacation home in Heathsville, you'll be on the waterfront, and 6 mi (9.7 km) from Northern Neck Farm Museum and 7 mi (11.2 km) from Cordreys ...
Opens in a new windowPrivate Dock and 200ft Shoreline w Panorama View
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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
74 Holiday Homes
Lowest Price
AU$264
Highest Price
AU$414
Popular accommodation
Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!, FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS, Cottage near the Bay, Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10, Steps to serene semi-private beach - Spring Getaway at "Bliss on the Bay", Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay, Bay Front Small Contemporary, Private 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed, Private Dock and 200ft Shoreline w Panorama View

Top trending hotels in Smith Island

Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!

Smith Island MD
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!
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK & golf cart rental

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK & golf cart rental

Smith Island MD
When you stay at this cottage in Smith Island, you'll be on the waterfront and steps from Terrapin Sand Point.
Opens in a new windowIDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK & golf cart rental
Summer is almost here on Smith Island! Get ready for a great season on the Bay

Summer is almost here on Smith Island! Get ready for a great season on the Bay

Smith Island MD
The price is AU$414 per night from 31 May to 1 June
AU$414
31 May - 1 June
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 windowSummer is almost here on Smith Island! Get ready for a great season on the Bay
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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 MD
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
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.