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Guest favourite
Home in Shady Side
Luxe Modern Chesapeake Waterfront Oasis - 5 Star
5 guests3 bedrooms3 beds2 baths
2–7 Jul
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2–7 Jul
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$1,886 NZD per night

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Top Guest favourite
Home in Shady Side
Canary Pointe-A popular getaway for 2!
2 beds
15–20 Apr
$366 NZD per night
4.97 out of 5 average rating, 152 reviews
Top Guest favourite
Home in Shady Side
Ruby Of The Bay
20–25 Apr
$558 NZD per night
5.0 out of 5 average rating, 17 reviews
Top Guest favourite
Home in Shady Side
Sunset Cottage
4 beds
9–14 May
$774 NZD per night
4.98 out of 5 average rating, 45 reviews
Guest favourite
Home in Shady Side
Waterfront Sanctuary only 50 Min. From DC/Balt.
12 beds
10–15 Apr
$1,517 NZD per night
4.96 out of 5 average rating, 78 reviews
Top Guest favourite
Home in Shady Side
"Pier Joy!" - 3BR Waterfront Home W/Private Dock
3 beds
14–19 Apr
$677 NZD per night
4.98 out of 5 average rating, 55 reviews
Guest favourite
Home in Shady Side
The Cottage
Free cancellation
27 Apr – 2 May
$525 NZD per night
4.96 out of 5 average rating, 52 reviews
Guest favourite
Home in Shady Side
Cozy Bay home w/180 degree view
3 beds
10–15 Apr
$490 NZD per night
4.93 out of 5 average rating, 45 reviews
Top Guest favourite
Home in West River
Cozy waterview home in West River!
3 beds
1–6 May
$454 NZD per night
4.98 out of 5 average rating, 115 reviews
Guest favourite
Home in Shady Side
Waterfront w/ Private Pier, 35 Mins to Annapolis
8 beds
11–16 Apr
$833 NZD per night
4.96 out of 5 average rating, 105 reviews
Superhost
Home in Shady Side
Chesapeake Bay - West River Home
5 beds
10–15 Apr
$934 NZD per night
4.83 out of 5 average rating, 12 reviews
Superhost
Home in Shady Side
Baydream Believer -Chesapeake Bay water community
6 beds
3–8 May
$790 NZD per night
4.87 out of 5 average rating, 38 reviews
Superhost
Home in Shady Side
Cattail Landing- Photographer's Waterfront Retreat
6 beds
26 Apr – 1 May
$803 NZD per night
4.88 out of 5 average rating, 181 reviews
Cottage in Shady Side
Luxe Chesapeake Cabin * River View* Fire Pit*
Free cancellation
19–24 May
$602 NZD per night
4.9 out of 5 average rating, 40 reviews
Superhost
Home in Shady Side
Chesapeake Peace
2 beds
11–16 Apr
$455 NZD per night
4.87 out of 5 average rating, 30 reviews
Superhost
Room in Shady Side
Stay with SidcoHosting for 7 years,
The Wise Quack 2! Shared B
24 Sept – 1 Oct
$118 NZD per night
New place to stay
Superhost
Home in Shady Side
Water views from every window spacious round house
5 beds
23–28 Apr
$859 NZD per night
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Shady Side
Peaceful Waterfront Getaway
8 beds
10–15 Apr
$1,572 NZD per night
5.0 out of 5 average rating, 26 reviews
Home in West River
Zen Sunset Retreat (ZSR) on the Waterfront
6 beds
11–16 Apr
$1,168 NZD per night
New place to stay