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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
18–23 Aug
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5.0 out of 5 average rating, 17 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, 276 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
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, 7 reviews
Guest favourite
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
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, 81 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, 36 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
Guest favourite
Home in Deale
Franklin At The Bay
4 bedrooms, 9 beds, 2.5 bathrooms
18–23 Aug
4.84 out of 5 average rating, 25 reviews
Home in Shady Side
Steps to Chesapeake Bay! 'Callaway Drive Retreat'
3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
4.69 out of 5 average rating, 13 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
Top guest favourite
Home in Shady Side
Iconic Chesapeake. Unparalleled Luxury.
3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 211 reviews
Superhost
Home in Shady Side
Coastal Retreat | Water Views, Hot Tub, Sleeps 12
4 bedrooms, 6 beds, 3 bathrooms
19–24 Aug
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
Guest favourite
Home in Edgewater
House in Edgewater Maryland
5 bedrooms, 5 queen beds, 2 bathrooms
30 Aug – 4 Sept
4.91 out of 5 average rating, 192 reviews
Guest favourite
Cottage in Deale
Waterfront Cottage@ChesapeakeParadise Hot Tub/Dogs
3 bedrooms, 3 beds, 3 bathrooms
30 Aug – 4 Sept
4.83 out of 5 average rating, 200 reviews
Top guest favourite
Home in Deale
Charming Waterfront 3BR Cottage on Chesapeake Bay
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in North Beach
The Mermaid Cottage | Walk to Beach | Pet Friendly
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 21 reviews