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Search results; Over 1,000 homes in Princess Anne

Top guest favourite
Farm stay in Princess Anne
Farmhouse located on a horse farm
3 bedrooms, 4 beds, 2.5 shared bathrooms
28 Aug – 2 Sept
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4.95 out of 5 average rating, 118 reviews
Guest favourite
Home in Princess Anne
Countryside Home in Princess Anne
3 bedrooms, 3 beds, 2 bathrooms
19–24 Aug
4.98 out of 5 average rating, 45 reviews
Guest favourite
Home in Princess Anne
Peaceful Home Away from Home
2 bedrooms, 2 double beds, 1 bathroom
13–18 Sept
4.91 out of 5 average rating, 57 reviews
Superhost
Home in Princess Anne
Ye Ole Pirate House
3 bedrooms, 4 beds, 1 bathroom
9–14 Aug
4.87 out of 5 average rating, 38 reviews
Home in Princess Anne
Private Beach & Fishing Pier: Wicomico River House
4 bedrooms, 6 beds, 2.5 bathrooms
23–28 Aug
4.82 out of 5 average rating, 11 reviews
Guest favourite
Cottage in Princess Anne
Waterfront Cottage in Mt. Vernon
2 bedrooms, 2 beds, 1 bathroom
8–13 Aug
4.94 out of 5 average rating, 47 reviews
Superhost
Hotel in Princess Anne
King Room #6
1 bedroom, 1 king bed, 1 bathroom
11–16 Aug
Superhost
Hotel in Princess Anne
Washington Hotel Suite #3-4
1 bedroom, 3 beds, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Hotel in Princess Anne
Historic Room #1
1 bedroom, 1 queen bed, 1 bathroom
1–6 Aug
4.8 out of 5 average rating, 5 reviews
Top guest favourite
Cottage in Westover
Mary’s Cottage•at Old Beauchamp Homestead•
2 bedrooms, 2 beds, 2 bathrooms
1–6 Aug
4.93 out of 5 average rating, 69 reviews
Home in Westover
Waterfront Cottage on Goose Creek Westover, MD
3 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Fruitland
Johnna's House
3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
4.97 out of 5 average rating, 402 reviews
Home in Deal Island
House of the Setting Sun/Deal Island Bayfront Home
3 bedrooms, 7 beds, 2 bathrooms
16–21 Aug
4.84 out of 5 average rating, 45 reviews
Top guest favourite
Home in Deal Island
The Tangier Escape
2 bedrooms, 3 beds, 1.5 bathrooms
9–14 Aug
4.96 out of 5 average rating, 26 reviews
Home in Princess Anne
Waterfront Retreat with Private Beach, Dock & Lift
7 bedrooms, 10 beds, 4 bathrooms
9–14 Sept
Top guest favourite
Home in Crisfield
Marshall’s Retreat Chesapeake small town getaway
3 bedrooms, 5 beds, 2 bathrooms
21–26 Aug
4.99 out of 5 average rating, 103 reviews
Guest favourite
Tiny home in Salisbury
Cattail's Branch
1 bedroom, 2 beds, 1 bathroom
29 Aug – 3 Sept
4.83 out of 5 average rating, 233 reviews
Top guest favourite
Guest house in Pocomoke City
2 Bedroom Apartment
2 bedrooms, 3 beds, 1 bathroom
15–20 Aug
4.94 out of 5 average rating, 184 reviews
Guest favourite
Cottage in Westover
Dog-Friendly Westover Cottage w/ River Access!
2 bedrooms, 4 beds, 1 bathroom
17–22 Aug
4.88 out of 5 average rating, 67 reviews