
Vacation rentals in Smith Island
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Top-rated vacation rentals in Smith Island
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Smith Island vacation rentals
Other great vacation rentals in Smith Island
Top guest favourite

Home in Piney Point
5 out of 5 average rating, 36 reviewsWaterfront Studio | Bikes & Kayaks | Beach Access
Top guest favourite

Loft in White Stone
4.99 out of 5 average rating, 92 reviewsSerenity
Superhost

Cottage in Deal Island
4.63 out of 5 average rating, 249 reviewsDeal Island Bay Cottage - Maryland
Guest favourite

Home in Crisfield
4.97 out of 5 average rating, 65 reviewsCatch of the Bay
Superhost

Farm stay in Crisfield
4.73 out of 5 average rating, 15 reviewsHome of The Terrapin King
Guest favourite

Apartment in Park Hall
5 out of 5 average rating, 6 reviewsNEW Renovated Studio near St. Mary's City
Guest favourite

Cottage in Princess Anne
4.96 out of 5 average rating, 27 reviewsWaterfront Cottage in Mt. Vernon
Guest favourite

Loft in Onancock
4.93 out of 5 average rating, 14 reviewsCashville Studio
Quick stats about vacation rentals in Smith Island
Total rentals
10 properties
Nightly prices starting at
$28 CAD before taxes and fees
Total number of reviews
920 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Destinations to explore
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- Chesapeake Bay
- Assateague Island National Seashore
- Haven Beach
- Assateague Beach
- Bethel Beach
- Piney Point Beach
- Ragged Point Beach
- Cape Charles Beachfront
- Wilkins Beach
- Wallops Beach
- Gerry Boyle Park
- Saint Jerome Beach
- St George Island Beach
- Parramore Beach
- Guard Shore
- Marshalls Beach
- Oxford Beach
- Gargathy Beach
- Bow Beach
- Cove Point Beach
- Lane Beach
- General's Ridge Vineyard
- Sandyland Beach
- Cordreys Beach