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Search results; Over 1,000 homes in Shady Side

Top guest favourite
Home in Shady Side
Iconic Chesapeake. Unparalleled Luxury.
3 bedrooms, 3 beds, 2 private bathrooms
23–28 Sept
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5.0 out of 5 average rating, 215 reviews
Top guest favourite
Home in Shady Side
Canary Pointe-A popular getaway for 2!
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 284 reviews
Top guest favourite
Home in Shady Side
Waterfront Sanctuary only 50 Min. From DC/Balt.
5 bedrooms, 12 beds, 4 bathrooms
13–18 Sept
4.97 out of 5 average rating, 111 reviews
Top guest favourite
Home in Shady Side
Waterfront Coastal Retreat w/ Beach Access
3 bedrooms, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 10 reviews
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, 32 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, 60 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, 37 reviews
Top guest favourite
Home in Shady Side
Peaceful Coastal Escape | Water Views + Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Shady Side
Sunset Cottage
2 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
4.99 out of 5 average rating, 82 reviews
Top guest favourite
Cottage in Tracys Landing
Charming Waterfront on Chesapeake Bay
4 bedrooms, 6 beds, 1 bathroom
26–31 Oct
4.9 out of 5 average rating, 405 reviews
Guest favourite
Home in Deale
Heaven Sent
6 bedrooms, 8 beds, 3 bathrooms
8–13 Sept
5.0 out of 5 average rating, 10 reviews
Superhost
Home in Deale
Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home
4 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
4.85 out of 5 average rating, 104 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
Top guest favourite
Home in Edgewater
Chesapeake Bay Waterfront Escape
3 bedrooms, 7 beds, 2 bathrooms
8–13 Sept
4.88 out of 5 average rating, 40 reviews
Home in Shady Side
Waterside Retreat in Shady Side, Maryland
3 bedrooms, 3 beds, 2 bathrooms
22–27 Sept
4.63 out of 5 average rating, 8 reviews
Guest favourite
Home in Shady Side
West River Waterfront w/ Pier, Kayaks & Bay Views
4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
4.83 out of 5 average rating, 23 reviews
Guest favourite
Home in Edgewater
Edgewater's Shelby on the Bay
4 bedrooms, 6 beds, 3 bathrooms
8–13 Sept
4.91 out of 5 average rating, 23 reviews
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, 168 reviews
Home in Shady Side
Steps to Chesapeake Bay! 'Callaway Drive Retreat'
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.71 out of 5 average rating, 14 reviews