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Search results; Over 1,000 homes in Tilghman Island

Superhost
Home in Tilghman Island
Pool, hot tub, and waterfront views
3 bedrooms, 5 beds, 3 shared baths
Aug 18 – 23
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4.6 out of 5 average rating, 5 reviews
Top guest favorite
Home in Tilghman Island
Island home with a fire pit and hammock
5.0 out of 5 average rating, 31 reviews, 3 bedrooms, 3 beds, 2 baths
Sep 8 – 13
Top guest favorite
Home in Tilghman Island
Waterfront cottage with panoramic harbor views
4.95 out of 5 average rating, 43 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 29 – Sep 3
Top guest favorite
Guest suite in Tilghman Island
Waterfront retreat with dock on the cove
4.97 out of 5 average rating, 180 reviews, 1 bedroom, 4 beds, 1 bath
Aug 23 – 28
Guest favorite
Home in Tilghman Island
Waterfront with pool, dock, and hot tub
4.96 out of 5 average rating, 45 reviews, 5 bedrooms, 8 beds, 4.5 baths
Sep 21 – 26
Guest favorite
Home in Tilghman Island
Waterfront cottage on Tilghman Island
5.0 out of 5 average rating, 37 reviews, 3 bedrooms, 4 beds, 2.5 baths
Sep 27 – Oct 2
Guest favorite
Home in Tilghman Island
Renovated cottage with a screened porch
4.8 out of 5 average rating, 15 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 21 – 26
Guest favorite
Home in Tilghman Island
Tilghman Island, half-mile to the marina
4.95 out of 5 average rating, 20 reviews, 2 bedrooms, 3 beds, 2 baths
Aug 26 – 31
Guest favorite
Home in Tilghman Island
Private pier on the Chesapeake Bay
4.94 out of 5 average rating, 53 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 18 – 23
Top guest favorite
Cottage in Wittman
Waterfront with kayaks, dock, and sunsets
4.9 out of 5 average rating, 198 reviews, 3 bedrooms, 3 beds, 2 baths
Oct 27 – Nov 1
Superhost
Home in Tilghman Island
Private dock on the Chesapeake Bay
4.82 out of 5 average rating, 17 reviews, 3 bedrooms, 3 beds, 2 baths
Sep 24 – 29
Superhost
Home in Tilghman Island
Waterfront with a pool and private dock
4 bedrooms, 6 beds, 3 baths
Aug 29 – Sep 3
Top guest favorite
Home in Deale
8-acre waterfront with a 140-foot dock
4.98 out of 5 average rating, 149 reviews, 3 bedrooms, 4 beds, 2 baths
Oct 27 – Nov 1
Top guest favorite
Apartment in Stevensville
Modern farmhouse vibe with a pool
4.97 out of 5 average rating, 311 reviews, 1 bedroom, 1 bed, 1 bath
Aug 16 – 21
Top guest favorite
Hotel room in Oxford
Private beach on a 19th-century estate
4.95 out of 5 average rating, 59 reviews, 1 bedroom, 1 bed, 1 bath
Aug 23 – 28
Home in Huntingtown
Private beach with kayaks and a firepit
New place to stay, 5 bedrooms, 4 beds, 3 baths
Aug 21 – 26
Top guest favorite
Cottage in Annapolis
Mill Creek views from a wooded porch
4.97 out of 5 average rating, 469 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 30 – Sep 4
Top guest favorite
Home in Cambridge
Waterfront lighthouse-styled home on 13 acres
4.99 out of 5 average rating, 222 reviews, 3 bedrooms, 5 beds, 2 baths
Aug 23 – 28
Guest favorite
Home in St. Michaels
Newly renovated, a mile from Saint Michaels
4.94 out of 5 average rating, 85 reviews, 3 bedrooms, 3 beds, 2 baths
Oct 25 – 30