House holiday rentals in Shady Side
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Top-rated house rentals in Shady Side
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Shady Side house rentals
House rentals with a pool
Home in Kent Narrows
5.0 out of 5 average rating, 278 reviewsChester Riverfront At Kent Narrows
19–26 Oct
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
4–11 Apr
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
15–22 Nov
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
28 Mar – 4 Apr
Home in Edgewater
4.97 out of 5 average rating, 30 reviewsEntire Beach House with Pool and Hot Tub
31 Oct – 7 Nov
Home in Annapolis
4.95 out of 5 average rating, 41 reviewsNaptown Suite
3–10 Jan
Home in Deale
5.0 out of 5 average rating, 10 reviewsModern Bay Dream
2–9 Dec
Home in Edgewater
4.97 out of 5 average rating, 30 reviewsWaterfront | Pool | Hot tub | Beach Access
3–10 Oct
Weekly house rentals
Home in Shady Side
4.97 out of 5 average rating, 65 reviewsCanary Pointe-A popular getaway for 2!
8–15 Jul
Home in Shady Side
5.0 out of 5 average rating, 18 reviewsThe Cottage
6–13 Jan
Home in Shady Side
5.0 out of 5 average rating, 10 reviewsWaterfront Community by Bay | Sleeps 6 | Game Room
11–18 May
Home in Edgewater
4.95 out of 5 average rating, 38 reviewsRelaxing Turkey Point Retreat-Steps to the marina!
5–12 Feb
Home in Shady Side
4.88 out of 5 average rating, 24 reviewsCozy Bay home w/180 degree view
25 Jun – 2 Jul
Home in Shady Side
4.96 out of 5 average rating, 89 reviewsWaterfront w/ Private Pier, 35 Mins to Annapolis
19–26 Aug
Home in Shady Side
4.98 out of 5 average rating, 42 reviews"Pier Joy!" - 3BR Waterfront Home W/Private Dock
24 Jun – 1 Jul
Home in Shady Side
4.96 out of 5 average rating, 54 reviewsWaterfront Sanctuary only 50 Min. From DC/Balt.
30 Sep – 7 Oct
Private house rentals
Home in North Beach
5.0 out of 5 average rating, 95 reviewsWaterfront Home w/ Hot Tub, Pets ok, Peleton
30 Nov – 7 Dec
Home in Harwood
4.96 out of 5 average rating, 27 reviewsQuiet Farm Stay near Annapolis
4–11 Sep
Home in Edgewater
4.95 out of 5 average rating, 99 reviewsAnnapolis Area Waterside Retreat
30 Jan – 6 Feb
Home in Deale
4.95 out of 5 average rating, 21 reviewsChesapeake Paradise House-Stunning 6+br4ba Wtrfrnt
14–21 Sep
Home in Deale
5.0 out of 5 average rating, 8 reviewsQuiet Getaway in Waterfront Community
18–25 Jul
Home in North Beach
4.97 out of 5 average rating, 60 reviewsCharming Herrington / Rose Haven Cottage
29 Sep – 6 Oct
Home in North Beach
4.98 out of 5 average rating, 95 reviewsHuge Beach Bungalow- Yard, Beach Pass, King Beds
28 Jan – 4 Feb
Home in North Beach
4.98 out of 5 average rating, 47 reviewsCheerful Two Bedroom Home on the Chesapeake Bay!
6–13 Apr
Quick stats about house rentals in Shady Side
Total rentals
20 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
810 reviews
Nightly prices starting at
$151 NZD before taxes and fees
Destinations to explore
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- Monthly Rentals Shady Side
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