Smith Island vacation rentals
We found 26 vacation rentals — enter your dates for availability
Scroll through and select from vacation rentals in Smith Island to find one that's perfect for your trip. Whether you're staying in a vacation rental with your kids or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include a fireplace and a washer and dryer. You'll be sure to find a rental that has what everyone needs, including places that are non-smoking or accessible.
Find spaces that suit your style
Find the best place to stay - Smith Island
Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!
Sleeps 6 · 2 bedrooms · 2 bathrooms
Top rated rentals - Smith Island
Photo gallery for Get away to relax on Smith Island in the Chesapeake Bay
Smith Island Getaway
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value
The waterfront setting of Smith Island is ready to explore
The island views and other outdoor surroundings create an inviting atmosphere in Smith Island. There's no shortage of things to see and do in the area.A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.
Exploring the natural features in Smith Island
Whether you're looking for adventure or just want to spend some time taking in the scenery, Smith Island is a great place to get out in nature. These are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:
- Smith Island (0.9 mi / 1.4 km)
- Tangier Island (11 mi / 17.8 km)
- Point Lookout State Park (16.6 mi / 26.7 km)
- Shark Fin Shoal (16 mi / 25.8 km)