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Search results; Over 1,000 homes in Shady Side

Top guest favourite
Home in Shady Side
Peaceful Coastal Escape | Water Views + Hot Tub
3 bedrooms, 4 beds, 2 private bathrooms
21–26 Aug
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5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Shady Side
A Happy Place
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Home in Shady Side
Canary Pointe-A popular getaway for 2!
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 279 reviews
Top guest favourite
Home in Shady Side
Waterfront Sanctuary only 50 Min. From DC/Balt.
5 bedrooms, 12 beds, 4 bathrooms
20–25 Sept
4.97 out of 5 average rating, 109 reviews
Top guest favourite
Home in Shady Side
Iconic Chesapeake. Unparalleled Luxury.
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 211 reviews
Top guest favourite
Home in Shady Side
Sunset Cottage
2 bedrooms, 4 beds, 3 bathrooms
14–19 Sept
4.99 out of 5 average rating, 82 reviews
Guest favourite
Home in Shady Side
Waterfront Coastal Retreat w/ Beach Access
3 bedrooms, 1 bathroom
28 Aug – 2 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Shady Side
The Wise Quack 2 - A Taste of the Chesapeake Bay!
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.89 out of 5 average rating, 36 reviews
Guest favourite
Home in Shady Side
Peaceful Waterfront Getaway
6 bedrooms, 8 beds, 3.5 bathrooms
23–28 Aug
4.98 out of 5 average rating, 58 reviews
Superhost
Home in Shady Side
West River Waterfront w/ Pier, Kayaks & Bay Views
4 bedrooms, 5 beds, 3 bathrooms
22–27 Aug
4.82 out of 5 average rating, 22 reviews
Guest favourite
Home in Deale
Franklin At The Bay
4 bedrooms, 9 beds, 2.5 bathrooms
30 Aug – 4 Sept
4.85 out of 5 average rating, 26 reviews
Home in Shady Side
Steps to Chesapeake Bay! 'Callaway Drive Retreat'
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.69 out of 5 average rating, 13 reviews
Top guest favourite
Home in West River
Cozy waterview home in West River!
3 bedrooms, 3 beds, 2.5 bathrooms
8–13 Sept
4.97 out of 5 average rating, 167 reviews
Top guest favourite
Guest house in Galesville
Nautical Charm and Relaxing Waterview!
1 queen bed, 1 bathroom
21–26 Aug
4.95 out of 5 average rating, 187 reviews
Superhost
Home in Shady Side
Waterfront w/ Private Pier, 35 Mins to Annapolis
4 bedrooms, 8 beds, 2.5 bathrooms
21–26 Sept
4.91 out of 5 average rating, 123 reviews
Superhost
Home in Shady Side
Coastal Retreat | Water Views, Hot Tub, Sleeps 12
4 bedrooms, 6 beds, 3 bathrooms
22–27 Aug
Top guest favourite
Guest house in Edgewater
1 large room efficiency in detached garage.
1 bedroom, 1 queen bed, 1 bathroom
30 Nov – 5 Dec
4.99 out of 5 average rating, 173 reviews
Guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed, 1 bathroom
25–30 Aug
4.96 out of 5 average rating, 135 reviews
Guest favourite
Home in Edgewater
Waterfront Chesapeake Bay Sunrises & Fishing Dock!
2 bedrooms, 5 beds, 1 bathroom
6–11 Sept
4.98 out of 5 average rating, 181 reviews