Holiday Rentals in Smith Island
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Holiday Rentals in Smith Island

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

Historic home on Smith Island w/ dock!

Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage

Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island

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

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

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

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

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

Cottage near the Bay

Newly updated 3 bedroom cottage with Solo Stove fire pit

"Dragonfly" Waterfront Cottage on Chesapeake Bay

Bay Front Small Contemporary

Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!

Private Beach Front Getaway at The Sunshine Beach Cottage.

Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
Other types of properties in Smith Island you may be interested in

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart
Holiday Accommodation Smith Island
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Smith Island are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Smith Island itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Smith Island holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Smith Island, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Smith Island with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.










