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Enter dates and number of guests to see the total price per night.

24 places to stay

Entire house
Rating 4.65 out of 522 reviews
Priscilla's Place
8 guests · 3 bedrooms · 4 beds · 1 bath
Kitchen
SUPERHOST
Private room
Rating 4.95 out of 544 reviews
The Coffee Roaster's House
3 guests · 2 bedrooms · 3 beds · 1 shared bath
Kitchen · Wifi
Entire house
Rating 4.82 out of 522 reviews
Longbranch
6 guests · 3 bedrooms · 4 beds · 2.5 baths
Kitchen · Wifi
Entire cottage
Rating 4.92 out of 540 reviews
Levering Creek Cottage
4 guests · 2 bedrooms · 2 beds · 1 bath
Kitchen
Entire house
Rating 4.60 out of 55 reviews
Smith island home with private dock
12 guests · 4 bedrooms · 7 beds · 2 baths
Kitchen · Free parking
Entire cottage
Rating 5.0 out of 56 reviews
WATERFRONT : Soundview Cottage, Smith Island, MD
6 guests · 2 bedrooms · 5 beds · 1 bath
Kitchen · Wifi
Entire house
Rating 4.90 out of 541 reviews
Charming waterfront 2 BR cottage
4 guests · 2 bedrooms · 3 beds · 1 bath
Kitchen · Wifi
SUPERHOST
Entire house
Rating 4.80 out of 540 reviews
Smith Island Yummy Artist Retreat
4 guests · 2 bedrooms · 0 beds · 1.5 baths
Kitchen · Wifi
Entire house
Rating 4.81 out of 547 reviews
Smith Island Spectacular Sunsets!
11 guests · 4 bedrooms · 8 beds · 2 baths
Kitchen
Entire cottage
The Captains Cottage on Smith Island
8 guests · 3 bedrooms · 3 beds · 2 baths
Kitchen · Free parking
SUPERHOST
Entire house
Rating 4.82 out of 539 reviews
Chesapeake Get Away
4 guests · 2 bedrooms · 2 beds · 1 bath
Kitchen · Wifi · Free parking
Private room
Island Time B&B (Room #3-Queen room $175)
2 guests · 1 bedroom · 1 bed · 1 shared bath
Kitchen
Entire condominium
Rating 5.0 out of 56 reviews
Crisfield Condo with Spectacular Views
6 guests · 3 bedrooms · 4 beds · 2 baths
Kitchen · Wifi · Pool · Free parking
Island
Rating 4.33 out of 57 reviews
Oystermen's Pearl: A Smith Island Inn Cottage
6 guests · 3 bedrooms · 4 beds · 1.5 baths
Kitchen · Free parking
Entire condominium
Rating 4.75 out of 54 reviews
Crisfield Bayfront Condo
6 guests · 3 bedrooms · 4 beds · 2 baths
Kitchen · Wifi · Pool · Free parking
Private room
Island Time B&B (Room #4- Queen Room- $175)
2 guests · 1 bedroom · 1 bed · 1 private bath
Kitchen
Island
Michele's House, A Smith Island Inn Cottage
10 guests · 3 bedrooms · 9 beds · 2 baths
Kitchen · Wifi · Free parking
Private room
Island Time B&B(Room 1- 1st Floor-King- $189)
2 guests · 1 bedroom · 1 bed · 1 private bath
Kitchen
118 of 24 Rentals
Enter dates to see full pricing. Additional fees apply. Taxes may be added. Free cancellation only applicable within 48 hours from booking.