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Search results; Over 1,000 homes in Shady Side

Guest favourite
Home in Shady Side
Waterfront w/ Private Pier, 35 Mins to Annapolis
4 bedrooms, 8 beds, 2.5 private bathrooms
3–8 Aug
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4.94 out of 5 average rating, 122 reviews
Top guest favourite
Home in Shady Side
Canary Pointe-A popular getaway for 2!
1 bedroom, 2 beds
21–26 Aug
4.99 out of 5 average rating, 271 reviews
Top guest favourite
Home in Shady Side
A Happy Place
3 bedrooms, 5 beds
22–27 Aug
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Shady Side
Waterfront Sanctuary only 50 Min. From DC/Balt.
5 bedrooms, 12 beds
20–25 Sept
4.97 out of 5 average rating, 108 reviews
Top guest favourite
Home in Shady Side
Waterfront Coastal Retreat w/ Beach Access
3 bedrooms
24–29 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Shady Side
Sunset Cottage
2 bedrooms, 4 beds
14–19 Sept
4.99 out of 5 average rating, 79 reviews
Superhost
Home in Shady Side
West River Waterfront w/ Pier, Kayaks & Bay Views
4 bedrooms, 5 beds
22–27 Aug
4.81 out of 5 average rating, 21 reviews
Top guest favourite
Home in West River
Cozy waterview home in West River!
3 bedrooms, 3 beds
16–21 Aug
4.97 out of 5 average rating, 162 reviews
Home in Shady Side
Steps to Chesapeake Bay! 'Callaway Drive Retreat'
3 bedrooms, 4 beds
9–14 Aug
4.67 out of 5 average rating, 12 reviews
Top guest favourite
Home in Shady Side
Peaceful Coastal Escape | Water Views + Hot Tub
3 bedrooms, 4 beds
9–14 Aug
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Shady Side
Peaceful Waterfront Getaway
6 bedrooms, 8 beds
23–28 Aug
4.98 out of 5 average rating, 57 reviews
Top guest favourite
Home in Shady Side
Iconic Chesapeake. Unparalleled Luxury.
3 bedrooms, 3 beds
18–23 Aug
5.0 out of 5 average rating, 209 reviews
Guest favourite
Home in Shady Side
The Wise Quack 2 - A Taste of the Chesapeake Bay!
2 bedrooms, 4 beds
9–14 Sept
4.89 out of 5 average rating, 35 reviews
Guest favourite
Home in West River
Zen Sunset Retreat (ZSR) on the Waterfront
5 bedrooms, 8 beds
7–12 Sept
4.91 out of 5 average rating, 11 reviews
Guest favourite
Home in Deale
Franklin At The Bay
4 bedrooms, 9 beds
19–24 Aug
4.87 out of 5 average rating, 23 reviews
Top guest favourite
Home in Deale
Charming Waterfront 3BR Cottage on Chesapeake Bay
3 bedrooms, 4 beds
14–19 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Deale
8 Acre Waterfront Oasis! Pets are Free! 140ft Pier
3 bedrooms, 4 beds
23–28 Aug
4.98 out of 5 average rating, 146 reviews
Guest favourite
Home in Edgewater
House in Edgewater Maryland
5 bedrooms, 5 queen beds
30 Aug – 4 Sept
4.91 out of 5 average rating, 188 reviews
Guest favourite
Home in Deale
Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home
4 bedrooms, 5 beds
7–12 Aug
4.88 out of 5 average rating, 102 reviews