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Search results; Over 1,000 homes in Shady Side

Top guest favourite
Home in Shady Side
Sunset Cottage
2 bedrooms, 4 beds, 3 private bathrooms
14–19 Sept
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4.99 out of 5 average rating, 82 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
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
Iconic Chesapeake. Unparalleled Luxury.
3 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 211 reviews
Guest favourite
Home in Shady Side
Waterfront Coastal Retreat w/ Beach Access
3 bedrooms, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 8 reviews
Superhost
Home in Shady Side
West River Waterfront w/ Pier, Kayaks & Bay Views
4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
4.82 out of 5 average rating, 22 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
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
Home in Shady Side
Peaceful Coastal Escape | Water Views + Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 17 reviews
Home in Shady Side
Steps to Chesapeake Bay! 'Callaway Drive Retreat'
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.69 out of 5 average rating, 13 reviews
Guest favourite
Home in Deale
Franklin At The Bay
4 bedrooms, 9 beds, 2.5 bathrooms
13–18 Sept
4.85 out of 5 average rating, 26 reviews
Guest favourite
Home in Shady Side
Peaceful Waterfront Getaway
6 bedrooms, 8 beds, 3.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 58 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
Guest favourite
Home in Annapolis
Nautical Luxe Retreat 6 Guests • 3 BDR • 2 Baths
3 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.96 out of 5 average rating, 149 reviews
Superhost
Home in West River
Cozy Bayside Retreat
2 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Shady Side
Coastal Retreat | Water Views, Hot Tub, Sleeps 12
4 bedrooms, 6 beds, 3 bathrooms
8–13 Sept
Top guest favourite
Guest house in Galesville
Nautical Charm and Relaxing Waterview!
1 queen bed, 1 bathroom
8–13 Sept
4.95 out of 5 average rating, 187 reviews
Guest favourite
Cottage in Deale
Waterfront Cottage@ChesapeakeParadise Hot Tub/Dogs
3 bedrooms, 3 beds, 3 bathrooms
14–19 Sept
4.83 out of 5 average rating, 201 reviews