Search results; Over 1,000 places

Top guest favorite
Home in Shady Side
Luxe Modern Chesapeake Waterfront Oasis - 5 Star
1 min walk
Jul 6 – 11
ﺩ.ﺇ10,857 for 5 nights, originally ﺩ.ﺇ12,574
for 5 nights
5.0 out of 5 average rating, 164 reviews
Guest favorite
Home in Shady Side
Ruby Of The Bay
2 min walk
Jun 9 – 14
ﺩ.ﺇ5,467 for 5 nights
for 5 nights
4.95 out of 5 average rating, 22 reviews
Top guest favorite
Home in Shady Side
Canary Pointe-A popular getaway for 2!
10 min drive
May 11 – 16
ﺩ.ﺇ3,121 for 5 nights
for 5 nights
4.97 out of 5 average rating, 159 reviews
Superhost
Home in Shady Side
Cattail Landing- Photographer's Waterfront Retreat
1 min walk
Jun 11 – 16
ﺩ.ﺇ7,405 for 5 nights
for 5 nights
4.88 out of 5 average rating, 181 reviews
Guest favorite
Home in Shady Side
Waterfront w/ Private Pier, 35 Mins to Annapolis
7 min walk
May 11 – 16
ﺩ.ﺇ7,685 for 5 nights
for 5 nights
4.96 out of 5 average rating, 105 reviews
Guest favorite
Home in Shady Side
The Wise Quack 2 - A Taste of the Chesapeake Bay!
10 min drive
Jul 7 – 12
ﺩ.ﺇ3,268 for 5 nights
for 5 nights
5.0 out of 5 average rating, 10 reviews
Top guest favorite
Home in West River
Cozy waterview home in West River!
10 min drive
May 11 – 16
ﺩ.ﺇ3,766 for 5 nights
for 5 nights
4.98 out of 5 average rating, 119 reviews
Top guest favorite
Home in Shady Side
Sunset Cottage
10 min drive
Jun 16 – 21
ﺩ.ﺇ7,392 for 5 nights
for 5 nights
4.98 out of 5 average rating, 49 reviews
Top guest favorite
Guesthouse in Annapolis
Coastal Waterfront 1 Bedroom Cottage
30 min drive
Jun 1 – 6
ﺩ.ﺇ7,598 for 5 nights
for 5 nights
4.99 out of 5 average rating, 162 reviews
Top guest favorite
Home in Edgewater
Waterfront home on the Bay
20 min drive
May 29 – Jun 3
ﺩ.ﺇ6,780 for 5 nights
for 5 nights
5.0 out of 5 average rating, 11 reviews
Superhost
Room in Shady Side
The Wise Quack 2! Shared B
10 min drive
Sep 24 – Oct 1
ﺩ.ﺇ1,528 for 7 nights
for 7 nights
New place to stay
Top guest favorite
Home in Edgewater
Entire Beach House with Pool and Hot Tub
10 min drive
Jun 6 – 11
ﺩ.ﺇ7,318 for 5 nights
for 5 nights
4.98 out of 5 average rating, 53 reviews
Room in Annapolis
“Room at the Inn…”
30 min drive
May 11 – 16
ﺩ.ﺇ1,614 for 5 nights
for 5 nights
5.0 out of 5 average rating, 3 reviews
Guest favorite
Guesthouse in Galesville
Nautical Charm and relaxing waterview!
10 min drive
Jun 17 – 22
ﺩ.ﺇ3,853 for 5 nights
for 5 nights
4.95 out of 5 average rating, 170 reviews
Top guest favorite
Guesthouse in Edgewater
1 large room efficiency in detached garage.
30 min drive
Jun 23 – 28
ﺩ.ﺇ2,152 for 5 nights
for 5 nights
4.98 out of 5 average rating, 107 reviews
Guest favorite
Home in Shady Side
Peaceful Waterfront Getaway
8 min walk
May 11 – 16
ﺩ.ﺇ16,134 for 5 nights
for 5 nights
5.0 out of 5 average rating, 26 reviews
Guest favorite
Home in Edgewater
Spacious 3 Bedrooms House+Patio+Playground
30 min drive
May 27 – Jun 1
ﺩ.ﺇ3,315 for 5 nights, originally ﺩ.ﺇ4,067
for 5 nights
4.94 out of 5 average rating, 124 reviews
Guest favorite
Home in Shady Side
Waterfront Sanctuary only 50 Min. From DC/Balt.
10 min drive
May 11 – 16
ﺩ.ﺇ13,991 for 5 nights
for 5 nights
4.96 out of 5 average rating, 80 reviews