Search results; Over 1,000 places in Saint Michaels

The home you selected

Guest favorite
Home in Saint Michaels
SM’s Premier Rental Heated Pool opens 4/11/2025
4 guests2 bedrooms2 beds2 baths
Jul 20 – 25
More
Jul 20 – 25
More
R81,039 ZAR for 5 nights
for 5 nights

Explore more homes

Top guest favorite
Cottage in Saint Michaels
The Little Anchor Cottage, St. Michaels, MD
4 beds
Jun 1 – 6
R29,019 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 231 reviews
Top guest favorite
Home in Saint Michaels
Margaret Wells House - New
Free cancellation
Jul 11 – 16
R41,916 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 6 reviews
Top guest favorite
Apartment in Saint Michaels
Blue Crab Lodge
Free cancellation
Jun 8 – 13
R30,954 ZAR for 5 nights
for 5 nights
4.96 out of 5 average rating, 85 reviews
Guest favorite
Home in Saint Michaels
Small Historic House Downtown St Michaels
Free cancellation
Aug 25 – 30
R20,765 ZAR for 5 nights
for 5 nights
4.89 out of 5 average rating, 195 reviews
Top guest favorite
Home in Saint Michaels
Grace Cottage, Saint Michaels Walk to everything!
2 beds
Jun 8 – 13
R63,949 ZAR for 5 nights
for 5 nights
4.99 out of 5 average rating, 166 reviews
Guest favorite
Guest suite in Saint Michaels
Gorgeous Cottage: Easy Walk into St Michaels Town!
4 beds
Jun 23 – 28
R17,712 ZAR for 5 nights
for 5 nights
4.78 out of 5 average rating, 357 reviews
Top guest favorite
Room in Saint Michaels
Stay with Woody & Gussie
Secluded water - bedroom, sitting room, full bath!
May 26 – 31
R22,733 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 15 reviews
Guest favorite
Apartment in Saint Michaels
Charming Studio in the heart of St. Michael's, MD.
2 beds
May 26 – 31
R32,351 ZAR for 5 nights
for 5 nights
4.91 out of 5 average rating, 171 reviews
Top guest favorite
Home in Saint Michaels
Shipwrights Cottage in Town!
Free cancellation
Jul 20 – 25
R29,557 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 97 reviews
Guest favorite
Apartment in Saint Michaels
Charming Apt. in St. Michaels
2 beds
May 25 – 30
R30,631 ZAR for 5 nights
for 5 nights
4.96 out of 5 average rating, 49 reviews
Home in Saint Michaels
Historic Retreat in St. Michaels
3 beds
Jul 17 – 22
R42,325 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 3 reviews
Top guest favorite
Cottage in Saint Michaels
La Casita on Harris Creek, St. Michaels
Free cancellation
May 27 – Jun 1
R52,556 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 162 reviews
Top guest favorite
Cottage in Oxford
Sailor's Cottage - Private Waterfront
Free cancellation
May 28 – Jun 2
R49,740 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 13 reviews
Top guest favorite
Boutique hotel in Oxford
Water View with Beach, Walk to restaurants & shops
Free cancellation
Jun 16 – 22
R22,441 ZAR for 6 nights
for 6 nights
4.91 out of 5 average rating, 67 reviews
Guest favorite
Cottage in Wittman
"Imagine Acre" on Maryland's Eastern Shore
Free cancellation
May 26 – 31
R19,883 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 11 reviews
Top guest favorite
Apartment in Saint Michaels
Saint Michaels Luxury Get Away
4 beds
Jun 1 – 6
R66,099 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 39 reviews
Guest favorite
Hotel room in Oxford
Chesapeake Bay Hotel with Beach -Walk to Eat, Shop
Free cancellation
Jun 16 – 21
R20,318 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 33 reviews
Top guest favorite
Guest suite in Grasonville
Heron's Haven
1 bed
May 25 – 30
R11,124 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 91 reviews