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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
1–6 Sept
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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, 1 bathroom
21–26 Aug
4.99 out of 5 average rating, 273 reviews
Top guest favourite
Home in Shady Side
Waterfront Sanctuary only 50 Min. From DC/Balt.
5 bedrooms, 12 beds, 4 bathrooms
16–21 Aug
4.97 out of 5 average rating, 109 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
Guest favourite
Home in Shady Side
Waterfront Coastal Retreat w/ Beach Access
3 bedrooms, 1 bathroom
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, 3 bathrooms
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, 3 bathrooms
22–27 Aug
4.81 out of 5 average rating, 21 reviews
Top guest favourite
Home in Shady Side
Peaceful Coastal Escape | Water Views + Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Shady Side
The Wise Quack 2 - A Taste of the Chesapeake Bay!
2 bedrooms, 4 beds, 1 bathroom
9–14 Sept
4.89 out of 5 average rating, 35 reviews
Top guest favourite
Home in Shady Side
Iconic Chesapeake. Unparalleled Luxury.
3 bedrooms, 3 beds, 2 bathrooms
18–23 Aug
5.0 out of 5 average rating, 210 reviews
Home in Shady Side
Waterside Retreat in Shady Side, Maryland
3 bedrooms, 3 beds, 2 bathrooms
28 Aug – 2 Sept
4.67 out of 5 average rating, 6 reviews
Top guest favourite
Home in West River
Cozy waterview home in West River!
3 bedrooms, 3 beds, 2.5 bathrooms
16–21 Aug
4.97 out of 5 average rating, 164 reviews
Superhost
Home in Shady Side
Coastal Retreat | Water Views, Hot Tub, Sleeps 12
4 bedrooms, 6 beds, 3 bathrooms
9–14 Aug
Home in Shady Side
Steps to Chesapeake Bay! 'Callaway Drive Retreat'
3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
4.67 out of 5 average rating, 12 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, 57 reviews
Guest favourite
Home in Deale
Franklin At The Bay
4 bedrooms, 9 beds, 2.5 bathrooms
19–24 Aug
4.84 out of 5 average rating, 25 reviews
Superhost
Home in West River
Cozy Bayside Retreat
2 bedrooms, 4 beds, 1.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Place to stay in Shady Side
Round House -- Panoramic Views -- Chesapeake Bay
3 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
4.96 out of 5 average rating, 48 reviews
Top guest favourite
Home in Deale
Charming Waterfront 3BR Cottage on Chesapeake Bay
3 bedrooms, 4 beds, 2 bathrooms
12–17 Oct
5.0 out of 5 average rating, 8 reviews