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Search results; Over 1,000 homes in Saint Michaels

Top guest favourite
Cottage in Saint Michaels
La Casita on Harris Creek, St. Michaels
1 bedroom, 2 beds, 1 private bathroom
15–20 Aug
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4.97 out of 5 average rating, 192 reviews
Top guest favourite
Flat in Saint Michaels
Blue Crab Lodge
2 bedrooms, 3 beds
19–24 Jul
4.97 out of 5 average rating, 151 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds
12–17 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Cambridge
Relaxing Retreat on the Hudson
5 bedrooms, 5 beds
24–29 Aug
4.96 out of 5 average rating, 72 reviews
Top guest favourite
Home in Tilghman Island
The Getaway
3 bedrooms, 3 beds
8–13 Sept
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Flat in Saint Michaels
Charming Studio in the heart of St. Michael's, MD.
2 beds
26–31 Jul
4.92 out of 5 average rating, 225 reviews
Top guest favourite
Home in Saint Michaels
Shipwrights Cottage in Town!
2 bedrooms, 3 beds
9–14 Aug
4.99 out of 5 average rating, 162 reviews
Top guest favourite
Home in Cambridge
Sunset Breezes - quiet waterfront retreat
3 bedrooms, 5 beds
23–28 Aug
4.99 out of 5 average rating, 218 reviews
Guest favourite
Home in Grasonville
Private Waterfront Home W/ Hot Tub, Dock & Kayaks
3 bedrooms, 3 queen beds
16–21 Aug
4.95 out of 5 average rating, 306 reviews
Top guest favourite
Boutique hotel in Oxford
Hotel Special: Sandaway Suite & Beach - Oxford, MD
1 bedroom, 1 king bed
2–7 Aug
4.94 out of 5 average rating, 63 reviews
Guest favourite
Flat in Saint Michaels
Charming Apt. in St. Michaels
1 bedroom, 2 beds
26–31 Jul
4.96 out of 5 average rating, 96 reviews
Guest favourite
Home in Saint Michaels
Private&Cozy/3br+2ba/1mi to town
3 bedrooms, 3 beds
27 Jul – 1 Aug
4.94 out of 5 average rating, 80 reviews
Top guest favourite
Cottage in Leonardtown
Beach Front and 'Perfectly Placed'
2 bedrooms, 3 beds
30 Aug – 4 Sept
4.96 out of 5 average rating, 262 reviews
Guest favourite
Cabin in Saint Michaels
True St. Michaels 6 Acre Waterfront w/heated pool
5 bedrooms, 11 beds
17–22 Jul
4.99 out of 5 average rating, 123 reviews
Guest favourite
Home in Wittman
Eastern Shore Cottage – Near St. Michaels Gateway
3 bedrooms, 3 beds
19–24 Jul
4.93 out of 5 average rating, 15 reviews
Top guest favourite
Cottage in Easton
Cottage on Solitude Creek, Hot Tub, Pool & Firepit
2 bedrooms, 3 beds
25–30 Aug
5.0 out of 5 average rating, 124 reviews
Top guest favourite
Home in Shady Side
Canary Pointe-A popular getaway for 2!
1 bedroom, 2 beds
21–26 Aug
4.99 out of 5 average rating, 268 reviews
Top guest favourite
Room in Saint Michaels
Secluded water - bedroom, sitting room, full bath!
2 single beds
10–15 Aug
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Home in Saint Michaels
Miles Aweigh
3 bedrooms, 4 beds
28 Sept – 3 Oct
4.97 out of 5 average rating, 290 reviews