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Search results; Over 1,000 places in Shady Side

Guest favourite
Home in Shady Side
Sunset Cottage
4 beds
Apr. 22 – 27
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Shady Side
Peaceful Waterfront Getaway
8 beds
Apr. 20 – 25
5.0 out of 5 average rating, 17 reviews
Superhost
Home in Shady Side
Cattail Landing- Photographer's Waterfront Retreat
6 beds
Apr. 20 – 25
4.88 out of 5 average rating, 174 reviews
Guest favourite
Home in Shady Side
Canary Pointe-A popular getaway for 2!
2 beds
May 14 – 19
4.97 out of 5 average rating, 64 reviews
Guest favourite
Home in Shady Side
Waterfront Sanctuary only 50 Min. From DC/Balt.
12 beds
Apr. 21 – 26
4.96 out of 5 average rating, 53 reviews
Guest favourite
Home in Shady Side
Luxe Modern Chesapeake Waterfront Oasis - 5 Star
3 beds
Jun. 28 – Jul. 3
5.0 out of 5 average rating, 116 reviews
Home in Shady Side
Chesapeake Peace
2 beds
Apr. 21 – 26
4.83 out of 5 average rating, 6 reviews
Superhost
Home in Shady Side
Cozy Bay home w/180 degree view
3 beds
Apr. 22 – 27
4.88 out of 5 average rating, 24 reviews
Guest favourite
Home in Shady Side
The Cottage
Apr. 21 – 26
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Shady Side
Waterfront w/ Private Pier, 35 Mins to Annapolis
8 beds
Apr. 20 – 25
4.96 out of 5 average rating, 89 reviews
Guest favourite
Home in Shady Side
Baydream Believer -Chesapeake Bay water community
6 beds
May 3 – 8
4.91 out of 5 average rating, 23 reviews
Guest favourite
Cottage in Shady Side
Tranquil Waterfront Cottage - 50 minutes to DC
3 beds
Apr. 28 – May 3
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Shady Side
"Pier Joy!" - 3BR Waterfront Home W/Private Dock
3 beds
Apr. 20 – 25
4.98 out of 5 average rating, 42 reviews
Guest favourite
Home in Shady Side
Waterfront Community by Bay | Sleeps 6 | Game Room
5 beds
Apr. 20 – 25
5.0 out of 5 average rating, 10 reviews
Guest favourite
Guesthouse in Galesville
Gorgeous water view studio!
1 queen bed
Apr. 22 – 27
4.95 out of 5 average rating, 163 reviews
Guest favourite
Home in West River
Cozy waterview home in West River!
May 6 – 11
4.97 out of 5 average rating, 72 reviews
Guest favourite
Cottage in Shady Side
Luxe Chesapeake Cabin * River View* Fire Pit*
7 beds
Apr. 23 – 28
4.9 out of 5 average rating, 29 reviews
Superhost
Bungalow in Deale
Cozy waterfront getaway on the Bay
2 queen beds
Apr. 20 – 25
4.86 out of 5 average rating, 355 reviews