House vacation 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.
Vacation 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, 279 reviewsChester Riverfront At Kent Narrows
Nov 2 – 9
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
Dec 4 – 11
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Nov 21 – 28
Home in Fairfax
4.96 out of 5 average rating, 145 reviews6BR Modern Home w/HEATED Pool & Screened in Porch
Dec 11 – 18
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
Mar 25 – Apr 1
Home in Annandale
4.85 out of 5 average rating, 190 reviewsLuxury HUGE 8 Bedroom Villa 15 min to DC Sleeps 27
Oct 30 – Nov 6
Home in Edgewater
4.97 out of 5 average rating, 30 reviewsEntire Beach House with Pool and Hot Tub
Oct 31 – Nov 7
Home in Annapolis
4.95 out of 5 average rating, 41 reviewsNaptown Suite
Jun 30 – Jul 7
Weekly house rentals
Home in Shady Side
4.97 out of 5 average rating, 67 reviewsCanary Pointe-A popular getaway for 2!
Apr 16 – 23
Home in Shady Side
5.0 out of 5 average rating, 18 reviewsThe Cottage
Dec 7 – 14
Home in Shady Side
4.88 out of 5 average rating, 25 reviewsCozy Bay home w/180 degree view
Mar 13 – 20
Home in Shady Side
4.96 out of 5 average rating, 55 reviewsWaterfront Sanctuary only 50 Min. From DC/Balt.
May 10 – 17
Home in Shady Side
4.91 out of 5 average rating, 23 reviewsBaydream Believer -Chesapeake Bay water community
Jul 21 – 28
Home in Shady Side
4.98 out of 5 average rating, 42 reviews"Pier Joy!" - 3BR Waterfront Home W/Private Dock
Jun 10 – 17
Home in Shady Side
4.96 out of 5 average rating, 89 reviewsWaterfront w/ Private Pier, 35 Mins to Annapolis
Oct 20 – 27
Home in Shady Side
5.0 out of 5 average rating, 10 reviewsWaterfront Community by Bay | Sleeps 6 | Game Room
Jun 24 – Jul 1
Private house rentals
Home in Edgewater
4.95 out of 5 average rating, 100 reviewsAnnapolis Area Waterside Retreat
Aug 24 – 31
Home in Deale
4.95 out of 5 average rating, 21 reviewsChesapeake Paradise House-Stunning 6+br4ba Wtrfrnt
Aug 15 – 22
Home in North Beach
5.0 out of 5 average rating, 95 reviewsWaterfront, Dog-friendly, Hot Tub, Peleton, Bikes
Dec 31 – Jan 7
Home in North Beach
4.98 out of 5 average rating, 96 reviewsHuge Beach Bungalow- Yard, Beach Pass, King Beds
Sep 27 – Oct 4
Home in Deale
5.0 out of 5 average rating, 8 reviewsQuiet Getaway in Waterfront Community
Jul 18 – 25
Home in Harwood
4.96 out of 5 average rating, 28 reviewsQuiet Farm Stay near Annapolis
Mar 21 – 28
Home in North Beach
4.97 out of 5 average rating, 61 reviewsCharming Herrington / Rose Haven Cottage
Sep 29 – Oct 6
Home in Annapolis
4.89 out of 5 average rating, 27 reviewsCute cozy rancher close to down town Annapolis
Nov 3 – 10
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
ﺩ.ﺇ331 before taxes and fees
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