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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

$1,944 SGD for 5 nights

,

4.95 out of 5 average rating, 118 reviews

Guest favourite

Home in Princess Anne

Peaceful Home Away from Home

2 bedrooms, 2 double beds, 1 bathroom

13–18 Sept

$762 SGD for 5 nights

4.91 out of 5 average rating, 57 reviews

Guest favourite

Home in Princess Anne

Countryside Home in Princess Anne

3 bedrooms, 3 beds, 2 bathrooms

19–24 Aug

$1,705 SGD for 5 nights

4.98 out of 5 average rating, 45 reviews

Superhost

Home in Princess Anne

Ye Ole Pirate House

3 bedrooms, 4 beds, 1 bathroom

9–14 Aug

$1,195 SGD for 5 nights

Free cancellation

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

$3,358 SGD for 5 nights

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

$1,455 SGD for 5 nights

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

$1,219 SGD for 5 nights

Superhost

Hotel in Princess Anne

Washington Hotel Suite #3-4

1 bedroom, 3 beds, 1 bathroom

1–6 Aug

$1,753 SGD for 5 nights

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

$1,372 SGD for 5 nights

4.8 out of 5 average rating, 5 reviews

Home in Deal Island

House of the Setting Sun/Deal Island Bayfront Home

3 bedrooms, 7 beds, 2 bathrooms

16–21 Aug

$2,108 SGD for 5 nights

4.84 out of 5 average rating, 45 reviews

Home in Westover

Waterfront Cottage on Goose Creek Westover, MD

3 bedrooms, 4 beds, 2 bathrooms

24–29 Aug

$2,071 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Home in Crisfield

Marshall’s Retreat Chesapeake small town getaway

3 bedrooms, 5 beds, 2 bathrooms

21–26 Aug

$1,452 SGD for 5 nights

4.99 out of 5 average rating, 103 reviews

Top guest favourite

Home in Deal Island

The Tangier Escape

2 bedrooms, 3 beds, 1.5 bathrooms

9–14 Aug

$963 SGD for 5 nights

4.96 out of 5 average rating, 26 reviews

Top guest favourite

Guest house in Pocomoke City

2 Bedroom Apartment

2 bedrooms, 3 beds, 1 bathroom

15–20 Aug

$1,303 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 184 reviews

Top guest favourite

Home in Fruitland

Johnna's House

3 bedrooms, 4 beds, 2 bathrooms

2–7 Aug

$1,338 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 402 reviews

Guest favourite

Guest suite in Crisfield

The Serenity House

3 bedrooms, 3 queen beds, 1.5 bathrooms

13–18 Sept

$587 SGD for 5 nights

Free cancellation

4.78 out of 5 average rating, 275 reviews

Guest favourite

Tiny home in Salisbury

Cattail's Branch

1 bedroom, 2 beds, 1 bathroom

29 Aug – 3 Sept

$701 SGD for 5 nights

4.83 out of 5 average rating, 233 reviews

Home in Princess Anne

Waterfront Retreat with Private Beach, Dock & Lift

7 bedrooms, 10 beds, 4 bathrooms

9–14 Sept

$7,015 SGD for 5 nights

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