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
Stay at this vacation home in Ridge. Enjoy a garden, laundry facilities, and patios. Popular attractions Saint Jerome Beach and Confederate Memorial Park are ...
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
Stay at this vacation home in Reedville. Enjoy free WiFi, private pools, and a garden. Popular attractions Smith Point Marina and Ginny Beach are located ...
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 NZ$312 per night from 29 Sept to 30 Sept
NZ$312
29 Sept - 30 Sept
includes taxes & fees
Stay at this vacation home in Crisfield. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Gov. Tawes Library and Crisfield ...
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
Book a stay at this family-friendly vacation home in Reedville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Reedville Historic District ...
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 NZ$406 per night from 22 Sept to 23 Sept
NZ$406
22 Sept - 23 Sept
includes taxes & fees
Stay at this vacation home in Reedville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Reedville Historic District and Reedville Fishermen's ...
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 NZ$1,658 per night from 7 Oct to 8 Oct
NZ$1,658
7 Oct - 8 Oct
includes taxes & fees
Book a stay at this beach vacation home in Scotland. Enjoy a beach locale, laundry facilities, and balconies. Popular attractions Confederate Memorial Park and ...
Opens in a new windowKentigern at Scotland Yards
Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!

Smith Island
Stay at this vacation home in Smith Island. Enjoy a garden, laundry facilities, and patios. Popular attractions Smith Island and Tylerton County Dock are located ...
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
Stay at this vacation home in Reedville. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Smith Point Marina and Reedville Historic District ...
Opens in a new windowPrivate, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!
Summerlee at Scotland Yards

Summerlee at Scotland Yards

Scotland
Stay at this vacation home in Scotland. Enjoy a beach locale, laundry facilities, and balconies. Popular attractions Confederate Memorial Park and 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
89 Holiday Homes
Lowest Price
NZ$312
Highest Price
NZ$1,658
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
Stay at this vacation home in Smith Island. Enjoy a garden, laundry facilities, and patios. Popular attractions Smith Island and Tylerton County Dock are located ...
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 NZ$581 per night from 20 Sept to 21 Sept
NZ$581
20 Sept - 21 Sept
includes taxes & fees
Stay at this vacation home in Smith Island. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Smith Island and Tylerton County Dock are located ...
Opens in a new windowKayak friendly home on the Chesapeake Bay with bikes, paddle board & 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
Stay at this cottage in Smith Island. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Smith Island and Tylerton County Dock are located ...
Opens in a new windowIDLE 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
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
Stay at this vacation home in Smith Island. Enjoy a garden, laundry facilities, and a pool table. Popular attractions Smith Island and Tylerton County Dock are ...
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
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.

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