Book Holiday Homes in Smith Island

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Featured Holiday Homes in Smith Island

Charming 3-bedroom house with WiFi, AC in peaceful Reedville

Charming 3-bedroom house with WiFi, AC in peaceful Reedville

2 out of 5
Reedville
The price is NZ$484 per night from 24 Dec to 25 Dec
NZ$484
includes taxes & fees
24 Dec - 25 Dec
Stay at this vacation home in Reedville. Enjoy air conditioning. Popular attractions Smith Point Marina and Buzzard's Point Marina are located nearby.
Charming 3-bedroom house with WiFi, AC in peaceful Reedville
Cottage near the Bay

Cottage near the Bay

Crisfield
The price is NZ$353 per night from 24 Dec to 25 Dec
NZ$353
includes taxes & fees
24 Dec - 25 Dec
Stay at this vacation home in Crisfield. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Somers Cove Marina and J. Millard ...
Cottage near the Bay
Waterfront Scotland Beach Retreat w/ Private Beach

Waterfront Scotland Beach Retreat w/ Private Beach

Ridge
Book a stay at this beach vacation home in Ridge. Enjoy a beach locale, a garden, and balconies. Popular attractions Confederate Memorial Park and Point Lookout ...
Waterfront Scotland Beach Retreat w/ Private Beach
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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
Stay at this vacation home in Heathsville. Enjoy free WiFi, a garden, and patios. Popular attractions Ginny Beach and Smith Point Marina are located nearby.
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier

Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier

Heathsville
Book a stay at this beach vacation home in Ophelia. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Ginny Beach and Smith Point Marina are ...
Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier
Virginia Retreat on Wicomico River w/ Dock!

Virginia Retreat on Wicomico River w/ Dock!

Burgess
Book a stay at this family-friendly vacation home in Burgess. Enjoy a garden, an in-room coffeemaker, and in-room fireplaces. Popular attractions Northern Neck ...
Virginia Retreat on Wicomico River w/ Dock!
Bay House with Amazing View & Swimming Pool (open May- Sept.)

Bay House with Amazing View & Swimming Pool (open May- Sept.)

Reedville
Stay at this vacation home in Reedville. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Reedville Fishermen's Museum and Reedville Historic ...
Bay House with Amazing View & Swimming Pool (open May- Sept.)
18-Acre Waterfront Sanctuary: Peace & Privacy

18-Acre Waterfront Sanctuary: Peace & Privacy

Ridge
Book a stay at this family-friendly vacation home in Ridge. Enjoy free WiFi, a garden, and patios. Popular attractions Confederate Memorial Park and Kitts Point ...
18-Acre Waterfront Sanctuary: Peace & Privacy
Waterfront Marion Station Retreat w/ Private Dock!

Waterfront Marion Station Retreat w/ Private Dock!

Marion Station
Stay at this vacation home in Marion Station. Enjoy an in-room coffeemaker, in-room fireplaces, and air conditioning. Popular attractions Somers Cove Marina ...
Waterfront Marion Station Retreat w/ Private Dock!
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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
NZ$353
Highest Price
NZ$491
Popular accommodation
Charming 3-bedroom house with WiFi, AC in peaceful Reedville, Cottage near the Bay, Waterfront Scotland Beach Retreat w/ Private Beach, Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10, Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier, Virginia Retreat on Wicomico River w/ Dock!, Bay House with Amazing View & Swimming Pool (open May- Sept.), 18-Acre Waterfront Sanctuary: Peace & Privacy, Waterfront Marion Station Retreat w/ Private Dock!

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, patios, and an in-room coffeemaker. Popular attractions Smith Island and Terrapin Sand Point are ...
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
Stay at this cottage in Smith Island. Enjoy free WiFi, a garden, and patios. Popular attractions Smith Island and Terrapin Sand Point are located nearby.
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
Stay at this vacation home in Smith Island. Enjoy free WiFi, balconies, and an in-room coffeemaker. Popular attractions Smith Island and Terrapin Sand Point ...
Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage
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Deal Island Bay Cottage

Deal Island Bay Cottage

Deal Island
The price is NZ$491 per night from 5 Jan to 6 Jan
NZ$491
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this cottage in Deal Island. Enjoy free WiFi, cable/satellite TV service, and an in-room coffeemaker. Popular attraction Shark Fin Shoal is located ...
Deal Island Bay Cottage
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.

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^Subject to availability and chosen travel dates.