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

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

2 out of 5
Reedville VA
The price is AU$333 per night from 22 Nov to 23 Nov
AU$333
22 Nov - 23 Nov
includes taxes & fees
Located in Reedville, this vacation home is by the sea, within a 10-minute drive of Reedville Fishermen's Museum and Reedville Historic District.
Opens in a new windowCharming 3-bedroom house with WiFi, AC& heat in peaceful Reedville
Private 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed

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

Reedville VA
When you stay at this vacation home in Reedville, you'll be on the waterfront, within a 5-minute drive of Fleeton Beach and Chesapeake Bay.
Opens in a new windowPrivate 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed
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Bay Estate | Luxe Waterfront Home w/ Private Pier, Main+Guest House, Bay Views

Bay Estate | Luxe Waterfront Home w/ Private Pier, Main+Guest House, Bay Views

Dameron MD
With a stay at this vacation home in Dameron, you'll be on the beach, just a 1-minute walk from Chesapeake Bay and 8 minutes by foot from Saint Jerome ...
Opens in a new windowBay Estate | Luxe Waterfront Home w/ Private Pier, Main+Guest House, Bay Views
River front Home built in 2021 with Private Pier

River front Home built in 2021 with Private Pier

Reedville VA
Located in Reedville, this vacation home is by the sea, a 3-minute drive from Smith Point Marina and 7 minutes from Reedville Fishermen's Museum.
Opens in a new windowRiver front Home built in 2021 with Private Pier
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

Ridge MD
With a stay at this vacation home in Ridge (Point Lookout), you'll be a 1-minute drive from Chesapeake Bay and 9 minutes from Confederate Memorial Park.
Opens in a new windowBeach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
Waterfront! - Cozy "Captain's Cottage" with hot tub!

Waterfront! - Cozy "Captain's Cottage" with hot tub!

Reedville VA
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 windowWaterfront! - Cozy "Captain's Cottage" with hot tub!
Bay Front Small Contemporary

Bay Front Small Contemporary

Reedville VA
Located in Reedville, this vacation home is on the waterfront, a 1-minute drive from Chesapeake Bay and 5 minutes from Reedville Fishermen's Museum.
Opens in a new windowBay Front Small Contemporary
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 VA
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!
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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
77 Holiday Homes
Lowest Price
AU$333
Highest Price
AU$492
Popular accommodation
Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!, Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville, Private 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed, Bay Estate | Luxe Waterfront Home w/ Private Pier, Main+Guest House, Bay Views, River front Home built in 2021 with Private Pier, Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks, Waterfront! - Cozy "Captain's Cottage" with hot tub!, Bay Front Small Contemporary, Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!

Top trending hotels in Smith Island

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 MD
The price is AU$492 per night from 22 Nov to 23 Nov
AU$492
22 Nov - 23 Nov
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
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!
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
Save an average of 15% on thousands of hotels when you're signed in
Swanendele Inn at St. Mary's Maryland

Swanendele Inn at St. Mary's Maryland

5 out of 5
49946 Airedele Rd Ridge MD
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 ...
Opens in a new windowSwanendele Inn at St. Mary's Maryland
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.