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 Saint Michaels
4.97 out of 5 average rating, 240 reviewsMiles Aweigh
Home in Kent Narrows
5.0 out of 5 average rating, 281 reviewsChester Riverfront At Kent Narrows
Home in Cambridge
4.96 out of 5 average rating, 102 reviewsWaterfront, Fabulous Home for Families with Pool!
Home in Queenstown
4.81 out of 5 average rating, 142 reviewsBay Breeze Retreat
Home in Severn
4.81 out of 5 average rating, 107 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
Home in Edgewater
4.97 out of 5 average rating, 30 reviewsEntire Beach House with Pool and Hot Tub
Home in Deale
5.0 out of 5 average rating, 11 reviewsModern Bay Dream
Home in Edgewater
4.97 out of 5 average rating, 34 reviewsWaterfront | Pool | Hot tub | Beach Access
Weekly house rentals
Home in Annapolis
4.95 out of 5 average rating, 356 reviewsNew Hotel Chic
Home in Stevensville
4.96 out of 5 average rating, 157 reviewsRelax on Kent Island in 3 Bedroom Home w/Waterview
Home in Stevensville
4.97 out of 5 average rating, 100 reviewsThe Kent Island House
Home in Cambridge
4.92 out of 5 average rating, 186 reviewsGuest House: Farm homestead
Home in North Beach
4.84 out of 5 average rating, 184 reviewsWarm Home Overlooking the Chesapeake Bay
Home in Annapolis
4.86 out of 5 average rating, 210 reviewsSpacious Home in Private Neighborhood with Beach
Home in Silver Spring
4.99 out of 5 average rating, 160 reviewsEntire Guest Suite/Apt in Silver Spring/FDA
Home in Cambridge
4.91 out of 5 average rating, 148 reviewsJewell on the Chesapeake
Private house rentals
Home in Shady Side
5.0 out of 5 average rating, 11 reviewsWaterfront Community by Bay | Sleeps 6 | Game Room
Home in Shady Side
4.96 out of 5 average rating, 57 reviewsWaterfront Sanctuary only 50 Min. From DC/Balt.
Home in Shady Side
4.98 out of 5 average rating, 43 reviews"Pier Joy!" - 3BR Waterfront Home W/Private Dock
Home in Shady Side
4.96 out of 5 average rating, 92 reviewsWaterfront w/ Private Pier, 35 Mins to Annapolis
Home in Shady Side
4.92 out of 5 average rating, 24 reviewsBaydream Believer -Chesapeake Bay water community
Home in Edgewater
4.96 out of 5 average rating, 45 reviewsRelaxing Turkey Point Retreat-Steps to the marina!
Home in Deale
4.99 out of 5 average rating, 86 reviewsPet-Friendly 8 Acre Waterfront Oasis ! 140ft Pier
Home in Shady Side
5.0 out of 5 average rating, 19 reviewsPeaceful Waterfront Getaway
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
$137 AUD before taxes and fees
Destinations to explore
- Baltimore Accommodation & holiday rentals
- Ocean City Accommodation & holiday rentals
- Cape May Holiday rentals
- Wildwood Holiday rentals
- Rehoboth Beach Accommodation & holiday rentals
- Arlington Accommodation & holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
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- Monthly Rentals Shady Side
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