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Search results; Over 1,000 homes in Shady Side

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Top guest favourite
Home in Shady Side
Iconic Chesapeake. Unparalleled Luxury.
3 bedrooms, 3 beds, 2 bathrooms
31 Oct – 5 Nov
5.0 out of 5 average rating, 217 reviews
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Top guest favourite
Home in Shady Side
Waterfront Sanctuary only 50 Min. From DC/Balt.
5 bedrooms, 12 beds, 4 bathrooms
2–7 Oct
4.97 out of 5 average rating, 113 reviews
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Top guest favourite
Home in Shady Side
Canary Pointe-A popular getaway for 2!
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
4.98 out of 5 average rating, 287 reviews
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Top guest favourite
Home in Shady Side
Waterfront Coastal Retreat w/ Beach Access
3 bedrooms, 1 bathroom
4–9 Nov
5.0 out of 5 average rating, 16 reviews
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Top guest favourite
Home in Shady Side
A Happy Place
3 bedrooms, 5 beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 34 reviews
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Guest favourite
Home in Shady Side
Peaceful Waterfront Getaway
6 bedrooms, 8 beds, 3.5 bathrooms
4–9 Oct
4.98 out of 5 average rating, 60 reviews
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Top guest favourite
Home in Shady Side
Sunset Cottage
2 bedrooms, 4 beds, 3 bathrooms
25–30 Oct
4.99 out of 5 average rating, 84 reviews
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Guest favourite
Home in Shady Side
West River Waterfront w/ Pier, Kayaks & Bay Views
4 bedrooms, 5 beds, 3 bathrooms
12–17 Oct
4.83 out of 5 average rating, 23 reviews
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Guest favourite
Home in Shady Side
The Wise Quack 2 - A Taste of the Chesapeake Bay!
2 bedrooms, 4 beds, 1 bathroom
23–28 Oct
4.89 out of 5 average rating, 38 reviews
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Top guest favourite
Home in West River
Cozy waterview home in West River!
3 bedrooms, 3 beds, 2.5 bathrooms
4–9 Oct
4.97 out of 5 average rating, 170 reviews
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Top guest favourite
Home in Shady Side
Peaceful Coastal Escape | Water Views + Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 18 reviews
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Home in Shady Side
Steps to Chesapeake Bay! 'Callaway Drive Retreat'
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.71 out of 5 average rating, 14 reviews
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Superhost
Home in Shady Side
Coastal Retreat | Hot Tub + Water Views
4 bedrooms, 6 beds, 3 bathrooms
4–9 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Deale
Franklin At The Bay. Bay Adventures!
4 bedrooms, 9 beds, 2.5 bathrooms
17–22 Oct
4.85 out of 5 average rating, 27 reviews
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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, 13 reviews
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Top guest favourite
Home in Deale
8 Acre Waterfront Oasis! Pets are Free! 140ft Pier
3 bedrooms, 4 beds, 2 bathrooms
27 Oct – 1 Nov
4.98 out of 5 average rating, 155 reviews
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Superhost
Home in Shady Side
Waterfront w/ Private Pier, 35 Mins to Annapolis
4 bedrooms, 8 beds, 2.5 bathrooms
1–6 Oct
4.91 out of 5 average rating, 123 reviews
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Top guest favourite
Guest house in Galesville
Nautical Charm and Relaxing Waterview!
1 queen bed, 1 bathroom
1–6 Oct
4.95 out of 5 average rating, 188 reviews