Holiday Rentals in Smith Island
More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers
Flexibility matters
24/7 support, so you can book with confidence
Unlock member prices with Mates Rates
You could save 10% or more on over 100,000 hotels right now.
Check rental availability in Smith Island
Holiday Rentals in Smith Island

Historic home on Smith Island w/ dock!

Summer is here on Smith Island! Come out and enjoy a great season on the Bay

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

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK & golf cart rental

Private sand beach on Chesapeake Bay--Great for Kids--Sunrise/Sunset Views

"Heron's Nest" Charming Tiny House on Chesapeake Bay-Boat Launch/Slip Included

Bay Front Small Contemporary

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

Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!

Cottage near the Bay

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

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Private Beach Front Getaway at The Sunshine Beach Cottage.

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

Romantic Chesapeake Bay Lighthouse-Style House Getaway

"Gull Cottage" Charming Tiny House on Chesapeake Bay-Boat Launch/Slip included
Other types of properties in Smith Island you may be interested in

Historic home on Smith Island w/ dock!
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.










