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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 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, 1 bathroom
21–26 Aug
4.99 out of 5 average rating, 271 reviews
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Home in Shady Side
A Happy Place
3 bedrooms, 5 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 27 reviews
Top 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
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Home in Shady Side
Sunset Cottage
2 bedrooms, 4 beds, 3 bathrooms
14–19 Sept
4.99 out of 5 average rating, 78 reviews
Top guest favourite
Home in Shady Side
Waterfront Sanctuary only 50 Min. From DC/Balt.
5 bedrooms, 12 beds, 4 bathrooms
9–14 Aug
4.97 out of 5 average rating, 107 reviews
Home in Shady Side
Steps to Chesapeake Bay! 'Callaway Drive Retreat'
3 bedrooms, 4 beds, 2 bathrooms
1–6 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, 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
25–30 Aug
4.89 out of 5 average rating, 35 reviews
Guest favourite
Rooms in Deale
Seaside comfort Private room in quiet community
3 bedrooms, 1 queen bed, 2 bathrooms
1–6 Aug
4.93 out of 5 average rating, 14 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, 209 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 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, 162 reviews
Guest favourite
Home in Shady Side
Peaceful Waterfront Getaway
6 bedrooms, 8 beds, 3.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 56 reviews
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Home in Deale
Charming Waterfront 3BR Cottage on Chesapeake Bay
3 bedrooms, 4 beds, 2 bathrooms
25–30 Aug
5.0 out of 5 average rating, 7 reviews
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Room in Deale
Sunrise Suite Exquisite Bay View Lux/Rom/Spiritual
1 bed, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Flat in Deale
Romantic Wtrfnt Flat w Hot Tub@Chesapeake Paradise
2 bedrooms, 2 beds, 1 bathroom
17–22 Aug
4.91 out of 5 average rating, 623 reviews
Guest favourite
Home in West River
Enchanting West River Retreat
2 bedrooms, 4 beds, 2 bathrooms
10–15 Aug
4.89 out of 5 average rating, 19 reviews
Top guest favourite
Room in Annapolis
“Room at the Inn…”
1 queen bed, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 31 reviews