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Search results; Over 1,000 places in Shady Side

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Home in Shady Side
Sunset Cottage
Hosted by Nicole
22–27 Apr
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Shady Side
Peaceful Waterfront Getaway
Hosted by Tanya
1–6 Apr
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Shady Side
Canary Pointe-A popular getaway for 2!
Hosted by Kirk And Diana
1–6 Apr
4.97 out of 5 average rating, 64 reviews
Guest favourite
Home in Shady Side
Waterfront Sanctuary only 50 Min. From DC/Balt.
Hosted by Marc
1–6 Apr
4.96 out of 5 average rating, 52 reviews
Superhost
Home in Shady Side
Cattail Landing- Photographer's Waterfront Retreat
Hosted by a business
1–6 Apr
4.88 out of 5 average rating, 174 reviews
Home in Shady Side
Chesapeake Peace
Hosted by Andrew
1–6 Apr
4.8 out of 5 average rating, 5 reviews
Guest favourite
Home in Shady Side
Waterfront w/ Private Pier, 35 Mins to Annapolis
Hosted by Ashley
2–7 Apr
4.95 out of 5 average rating, 88 reviews
Guest favourite
Home in Shady Side
Luxe Modern Chesapeake Waterfront Oasis - 5 Star
Hosted by Evan
20–25 Jun
5.0 out of 5 average rating, 113 reviews
Superhost
Home in Shady Side
Cozy Bay home w/180 degree view
Hosted by Madeline
1–6 Apr
4.87 out of 5 average rating, 23 reviews
Guest favourite
Home in Shady Side
The Cottage
Hosted by Haley
1–6 Apr
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Shady Side
"Pier Joy!" - 3BR Waterfront Home W/Private Dock
Hosted by Jeff
4–9 Apr
4.97 out of 5 average rating, 39 reviews
Superhost
Home in West River
Enchanting West River Retreat
Hosted by Rick
1–6 Apr
New place to stay
Guest favourite
Cottage in Shady Side
Luxe Chesapeake Cabin * River View* Fire Pit*
Hosted by Thierry
1–6 Apr
4.88 out of 5 average rating, 26 reviews
Guest favourite
Home in Shady Side
Baydream Believer -Chesapeake Bay water community
Hosted by a business
10–15 Apr
4.91 out of 5 average rating, 22 reviews
Guest favourite
Guest house in Galesville
Gorgeous water view studio!
Hosted by Pam
1–6 Apr
4.95 out of 5 average rating, 163 reviews
Guest favourite
Home in Shady Side
Waterfront Community by Bay | Sleeps 6 | Game Room
Hosted by Denis
3–8 Apr
5.0 out of 5 average rating, 10 reviews
Superhost
Home in Shady Side
Water views from every window unique round house
Hosted by a business
1–6 Apr
Guest favourite
Cottage in Shady Side
Tranquil Waterfront Cottage - 50 minutes to DC
Hosted by Sarah
28 Apr – 3 May
5.0 out of 5 average rating, 9 reviews