Search results; Over 1,000 places

Prices include all fees
Top guest favorite
Home in Shady Side
Luxe Modern Chesapeake Waterfront Oasis - 5 Star
1 min walk
Aug 4 – 9
ﺩ.ﺇ9,454 for 5 nights, originally ﺩ.ﺇ12,125
for 5 nights
5.0 out of 5 average rating, 167 reviews
Top guest favorite
Home in Shady Side
Ruby Of The Bay
2 min walk
Jun 15 – 20
ﺩ.ﺇ5,146 for 5 nights
for 5 nights
4.96 out of 5 average rating, 24 reviews
Top guest favorite
Home in Shady Side
Canary Pointe-A popular getaway for 2!
10 min drive
Jun 15 – 20
ﺩ.ﺇ3,405 for 5 nights
for 5 nights
4.98 out of 5 average rating, 166 reviews
Superhost
Home in Shady Side
Cattail Landing- Photographer's Waterfront Retreat
1 min walk
Jun 22 – 27
ﺩ.ﺇ7,405 for 5 nights
for 5 nights
4.88 out of 5 average rating, 181 reviews
Guest favorite
Home in Shady Side
The Cottage
10 min drive
Jun 15 – 20
ﺩ.ﺇ4,843 for 5 nights
for 5 nights
4.96 out of 5 average rating, 54 reviews
Guest favorite
Home in Shady Side
The Wise Quack 2 - A Taste of the Chesapeake Bay!
10 min drive
Jul 7 – 12
ﺩ.ﺇ3,539 for 5 nights
for 5 nights
5.0 out of 5 average rating, 10 reviews
Guest favorite
Home in Shady Side
Waterfront w/ Private Pier, 35 Mins to Annapolis
7 min walk
Jun 2 – 7
ﺩ.ﺇ7,685 for 5 nights
for 5 nights
4.96 out of 5 average rating, 106 reviews
Top guest favorite
Home in Shady Side
Sunset Cottage
10 min drive
Jun 22 – 27
ﺩ.ﺇ7,887 for 5 nights
for 5 nights
4.98 out of 5 average rating, 51 reviews
Guest favorite
Home in Shady Side
Peaceful Waterfront Getaway
8 min walk
Jun 1 – 6
ﺩ.ﺇ18,115 for 5 nights
for 5 nights
5.0 out of 5 average rating, 28 reviews
Cottage in Shady Side
Luxe Chesapeake Cabin * River View* Fire Pit*
10 min drive
Jun 2 – 7
ﺩ.ﺇ4,628 for 5 nights
for 5 nights
4.9 out of 5 average rating, 41 reviews
Top guest favorite
Home in Edgewater
Annapolis Area Waterside Retreat
20 min drive
Jun 16 – 21
ﺩ.ﺇ8,244 for 5 nights
for 5 nights
4.97 out of 5 average rating, 183 reviews
Guest favorite
Home in Shady Side
Waterfront Sanctuary only 50 Min. From DC/Balt.
10 min drive
Jun 1 – 6
ﺩ.ﺇ13,991 for 5 nights
for 5 nights
4.96 out of 5 average rating, 83 reviews
Home in Shady Side
A Happy Place
10 min drive
Jul 14 – 19
ﺩ.ﺇ4,982 for 5 nights, originally ﺩ.ﺇ5,815
for 5 nights
Top guest favorite
Home in West River
Cozy waterview home in West River!
10 min drive
Jun 10 – 15
ﺩ.ﺇ4,507 for 5 nights
for 5 nights
4.98 out of 5 average rating, 123 reviews
Guest favorite
Guesthouse in Galesville
Nautical Charm and relaxing waterview!
10 min drive
Jun 24 – 29
ﺩ.ﺇ3,853 for 5 nights
for 5 nights
4.95 out of 5 average rating, 170 reviews
Top guest favorite
Home in Shady Side
"Pier Joy!" - 3BR Waterfront Home W/Private Dock
10 min drive
Jun 1 – 6
ﺩ.ﺇ8,395 for 5 nights, originally ﺩ.ﺇ11,149
for 5 nights
4.98 out of 5 average rating, 58 reviews
Top guest favorite
Home in Edgewater
Waterfront home on the Bay
20 min drive
Sep 19 – 24
ﺩ.ﺇ6,780 for 5 nights
for 5 nights
5.0 out of 5 average rating, 12 reviews
Top guest favorite
Home in Edgewater
Entire Beach House with Pool and Hot Tub
10 min drive
Aug 24 – 29
ﺩ.ﺇ6,888 for 5 nights
for 5 nights
4.98 out of 5 average rating, 54 reviews