Smith Island Holiday Homes
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Featured Holiday Homes in Smith Island

Beautiful Bayfront with Sanctuary Private Beach

Bay Front Small Contemporary

Walk to Local Eats & Docks! Crisfield Getaway

Waterfront 4-bedroom homestead with pool, jacuzzi, and dock access. Sleeps 11!

Historic home on Smith Island w/ dock!

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

Newly updated 3 bedroom cottage with Solo Stove fire pit

Harbor Master-Waterfront 3 bedroom home with endless pool pickleball fenced yard

Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay

Cottage near the Bay
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.
Smith Island Holiday Homes essential information
Accommodation | 69 Holiday Homes |
|---|---|
Lowest Price | NZ$208 |
Highest Price | NZ$612 |
Popular accommodation | Beautiful Bayfront with Sanctuary Private Beach , Bay Front Small Contemporary, Walk to Local Eats & Docks! Crisfield Getaway, Waterfront 4-bedroom homestead with pool, jacuzzi, and dock access. Sleeps 11!, Historic home on Smith Island w/ dock!, Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!, Newly updated 3 bedroom cottage with Solo Stove fire pit, Harbor Master-Waterfront 3 bedroom home with endless pool pickleball fenced yard, Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay, Cottage near the Bay, Romantic Chesapeake Bay Lighthouse-Style House Getaway, Kentigern Shed at Scotland Yards |
Top trending hotels in Smith Island

Historic home on Smith Island w/ dock!
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