Search results; Over 1,000 homes in Saint Michaels

Guest favorite
Apartment in Saint Michaels
Charming Studio in the heart of St. Michael's, MD.
Studio, 2 beds, 1 bath
Oct 5 – 10
ﺩ.ﺇ4,951 for 5 nights
,
4.91 out of 5 average rating, 196 reviews
Top guest favorite
Apartment in St. Michaels
Blue Crab Lodge
3 beds
Oct 12 – 17
ﺩ.ﺇ6,200 for 5 nights
4.97 out of 5 average rating, 111 reviews
Top guest favorite
Home in St. Michaels
Shipwrights Cottage in Town!
3 beds
Oct 5 – 10
ﺩ.ﺇ5,920 for 5 nights
4.99 out of 5 average rating, 123 reviews
Guest favorite
Home in St. Michaels
Small Historic House Downtown St Michaels
1 queen bed
Oct 20 – 25
ﺩ.ﺇ3,771 for 5 nights
4.89 out of 5 average rating, 214 reviews
Top guest favorite
Hotel room in Oxford
Water View with Beach, Walk to restaurants & shops
1 king bed
Oct 1 – 6
ﺩ.ﺇ4,714 for 5 nights
4.93 out of 5 average rating, 154 reviews
Guest favorite
Boutique hotel in Oxford
Water View with Beach, Walk to restaurants & shops
1 king bed
Oct 1 – 6
ﺩ.ﺇ4,714 for 5 nights
4.94 out of 5 average rating, 49 reviews
Top guest favorite
Home in St. Michaels
Grace Cottage, Saint Michaels Walk to everything!
2 beds
Oct 12 – 17
ﺩ.ﺇ8,933 for 5 nights
4.99 out of 5 average rating, 180 reviews
Top guest favorite
Cottage in St. Michaels
The Little Anchor Cottage, St. Michaels, MD
3 beds
Oct 12 – 17
ﺩ.ﺇ5,812 for 5 nights
4.98 out of 5 average rating, 252 reviews
Top guest favorite
Home in Leonardtown
White Point Cottage -- Quiet Waterfront Getaway
5 beds
Oct 1 – 6
ﺩ.ﺇ6,200 for 5 nights
5.0 out of 5 average rating, 135 reviews
Guest favorite
Cottage in St. Michaels
La Casita on Harris Creek, St. Michaels
2 beds
Oct 10 – 15
ﺩ.ﺇ11,086 for 5 nights
4.97 out of 5 average rating, 174 reviews
Top guest favorite
Home in Leonardtown
Water's Edge Cottage | Luxury Retreat
2 beds
Oct 17 – 22
ﺩ.ﺇ8,761 for 5 nights
4.99 out of 5 average rating, 94 reviews
Top guest favorite
Home in Easton
Arcadia Shores On The Cove
7 beds
Oct 1 – 6
ﺩ.ﺇ12,700 for 5 nights
5.0 out of 5 average rating, 7 reviews
Guest favorite
Cottage in Leonardtown
Beach Front and 'Perfectly Placed'
3 beds
Oct 1 – 6
ﺩ.ﺇ4,624 for 5 nights
4.96 out of 5 average rating, 223 reviews
Top guest favorite
Cottage in Wittman
"Wittman Cottage"
3 beds
Oct 23 – 28
ﺩ.ﺇ4,413 for 5 nights
4.9 out of 5 average rating, 173 reviews
Guest favorite
Hotel room in Oxford
Chesapeake Bay Hotel with Beach -Walk to Eat, Shop
1 king bed
Oct 1 – 6
ﺩ.ﺇ5,145 for 5 nights
4.95 out of 5 average rating, 42 reviews
Apartment in Easton
3Br/1Ba Pondview Langsdale House
3 beds
Oct 1 – 6
ﺩ.ﺇ6,165 for 5 nights
Top guest favorite
Houseboat in Kent Narrows
Cass-N-Reel Luxury Houseboat
1 bed
Oct 5 – 10
ﺩ.ﺇ3,983 for 5 nights
4.96 out of 5 average rating, 167 reviews
Top guest favorite
Room in Annapolis
Stay with JenniferHosting for 7 years,
Chesapeake Mornings
Oct 19 – 24
ﺩ.ﺇ1,486 for 5 nights
4.96 out of 5 average rating, 584 reviews
Home in Grasonville
Heron Point- 2 Acre Kent Narrows Waterfront Escape
7 beds
Oct 1 – 6
ﺩ.ﺇ8,001 for 5 nights
New place to stay