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shady side md
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Search results; Over 1,000 places in Shady Side
Over 1,000 places in Shady Side
Guest favourite
Guest favourite
Home in Shady Side
Sunset Cottage
4 beds
4 beds
Apr. 22 – 27
Apr. 22 – 27
$435 CAD
night
$435 CAD per night
·
$2,175 CAD total
$2,175 CAD total
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5.0 out of 5 average rating, 6 reviews
5.0 (6)
Guest favourite
Guest favourite
Home in Shady Side
Canary Pointe-A popular getaway for 2!
2 beds
2 beds
May 14 – 19
May 14 – 19
$295 CAD
night
$295 CAD per night
·
$1,477 CAD total
$1,477 CAD total
Show price breakdown
4.97 out of 5 average rating, 64 reviews
4.97 (64)
Home in Shady Side
Chesapeake Peace
2 beds
2 beds
Apr. 21 – 26
Apr. 21 – 26
$282 CAD
night
$282 CAD per night
·
$1,412 CAD total
$1,412 CAD total
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4.83 out of 5 average rating, 6 reviews
4.83 (6)
Superhost
Superhost
Home in Shady Side
Cozy Bay home w/180 degree view
3 beds
3 beds
Apr. 22 – 27
Apr. 22 – 27
$488 CAD
$402 CAD
night
$402 CAD per night, originally $488 CAD
·
$2,011 CAD total
$2,011 CAD total
Show price breakdown
4.88 out of 5 average rating, 24 reviews
4.88 (24)
Guest favourite
Guest favourite
Home in Shady Side
Luxe Modern Chesapeake Waterfront Oasis - 5 Star
3 beds
3 beds
Jun. 28 – Jul. 3
Jun. 28 – Jul. 3
$1,303 CAD
night
$1,303 CAD per night
·
$6,517 CAD total
$6,517 CAD total
Show price breakdown
5.0 out of 5 average rating, 116 reviews
5.0 (116)
Guest favourite
Guest favourite
Home in Shady Side
"Pier Joy!" - 3BR Waterfront Home W/Private Dock
3 beds
3 beds
Apr. 19 – 24
Apr. 19 – 24
$661 CAD
night
$661 CAD per night
·
$3,305 CAD total
$3,305 CAD total
Show price breakdown
4.98 out of 5 average rating, 42 reviews
4.98 (42)
Guest favourite
Guest favourite
Home in West River
Cozy waterview home in West River!
May 6 – 11
May 6 – 11
$330 CAD
night
$330 CAD per night
·
$1,648 CAD total
$1,648 CAD total
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4.97 out of 5 average rating, 72 reviews
4.97 (72)
Guest favourite
Guest favourite
Cottage in Shady Side
Tranquil Waterfront Cottage - 50 minutes to DC
3 beds
3 beds
Apr. 28 – May 3
Apr. 28 – May 3
$632 CAD
night
$632 CAD per night
·
$3,158 CAD total
$3,158 CAD total
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5.0 out of 5 average rating, 9 reviews
5.0 (9)
Guest favourite
Guest favourite
Cottage in Shady Side
Luxe Chesapeake Cabin * River View* Fire Pit*
7 beds
7 beds
Apr. 23 – 28
Apr. 23 – 28
$514 CAD
night
$514 CAD per night
·
$2,571 CAD total
$2,571 CAD total
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4.9 out of 5 average rating, 29 reviews
4.9 (29)
Guest favourite
Guest favourite
Home in Shady Side
Waterfront Sanctuary only 50 Min. From DC/Balt.
12 beds
12 beds
Apr. 21 – 26
Apr. 21 – 26
$1,147 CAD
night
$1,147 CAD per night
·
$5,734 CAD total
$5,734 CAD total
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4.96 out of 5 average rating, 53 reviews
4.96 (53)
Guest favourite
Guest favourite
Home in Shady Side
Peaceful Waterfront Getaway
8 beds
8 beds
Apr. 19 – 24
Apr. 19 – 24
$1,156 CAD
$962 CAD
night
$962 CAD per night, originally $1,156 CAD
·
$4,808 CAD total
$4,808 CAD total
Show price breakdown
5.0 out of 5 average rating, 16 reviews
5.0 (16)
Superhost
Superhost
Bungalow in Deale
Cozy waterfront getaway on the Bay
2 queen beds
2 queen beds
Apr. 20 – 25
Apr. 20 – 25
$321 CAD
night
$321 CAD per night
·
$1,604 CAD total
$1,604 CAD total
Show price breakdown
4.86 out of 5 average rating, 355 reviews
4.86 (355)
Guest favourite
Guest favourite
Home in Deale
8 Acre Pet-Friendly, Waterfront Oasis ! 140ft Pier
4 beds
4 beds
Apr. 21 – 26
Apr. 21 – 26
$469 CAD
night
$469 CAD per night
·
$2,347 CAD total
$2,347 CAD total
Show price breakdown
4.99 out of 5 average rating, 80 reviews
4.99 (80)
Guest favourite
Guest favourite
Home in Edgewater
Relaxing Turkey Point Retreat-Steps to the marina!
3 beds
3 beds
May 13 – 18
May 13 – 18
$253 CAD
night
$253 CAD per night
·
$1,263 CAD total
$1,263 CAD total
Show price breakdown
4.95 out of 5 average rating, 38 reviews
4.95 (38)
Guest favourite
Guest favourite
Home in Deale
Quiet Getaway in Waterfront Community
5 beds
5 beds
Apr. 22 – 27
Apr. 22 – 27
$459 CAD
night
$459 CAD per night
·
$2,295 CAD total
$2,295 CAD total
Show price breakdown
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Superhost
Superhost
Cottage in Deale
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
3 beds
3 beds
Apr. 23 – 28
Apr. 23 – 28
$406 CAD
night
$406 CAD per night
·
$2,029 CAD total
$2,029 CAD total
Show price breakdown
4.81 out of 5 average rating, 167 reviews
4.81 (167)
Guest favourite
Guest favourite
Home in Edgewater
Annapolis Area Waterside Retreat
4 queen beds
4 queen beds
May 5 – 10
May 5 – 10
$541 CAD
$376 CAD
night
$376 CAD per night, originally $541 CAD
·
$1,878 CAD total
$1,878 CAD total
Show price breakdown
4.95 out of 5 average rating, 96 reviews
4.95 (96)
Guest favourite
Guest favourite
Home in Deale
Hannah’s Hideaway
7 beds
7 beds
Apr. 25 – 30
Apr. 25 – 30
$432 CAD
night
$432 CAD per night
·
$2,161 CAD total
$2,161 CAD total
Show price breakdown
4.99 out of 5 average rating, 125 reviews
4.99 (125)
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