House vacation rentals in Shady Side
Find and book unique houses on Airbnb
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 Stevensville
5.0 out of 5 average rating, 103 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Home in Cambridge
4.96 out of 5 average rating, 101 reviewsWaterfront, Fabulous Home for Families with Pool!
Home in Kent Narrows
5.0 out of 5 average rating, 280 reviewsChester Riverfront At Kent Narrows
Home in Saint Michaels
4.97 out of 5 average rating, 239 reviewsMiles Aweigh
Home in New Market
4.93 out of 5 average rating, 117 reviewsHistoric Peace and Plenty Farm: Pool House
Home in Fairfax
4.96 out of 5 average rating, 147 reviews6BR Modern Home w/HEATED Pool & Screened in Porch
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Home in Severn
4.82 out of 5 average rating, 105 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
Weekly house rentals
Home in North Beach
4.83 out of 5 average rating, 181 reviewsWarm Home Overlooking the Chesapeake Bay
Home in Silver Spring
4.99 out of 5 average rating, 157 reviewsEntire Guest Suite/Apt in Silver Spring/FDA
Home in Shady Side
4.97 out of 5 average rating, 70 reviewsCanary Pointe-A popular getaway for 2!
Home in West River
4.97 out of 5 average rating, 76 reviewsCozy waterview home in West River!
Home in Shady Side
5.0 out of 5 average rating, 20 reviewsThe Cottage
Home in Shady Side
5.0 out of 5 average rating, 11 reviewsWaterfront Community by Bay | Sleeps 6 | Game Room
Home in Edgewater
4.95 out of 5 average rating, 43 reviewsRelaxing Turkey Point Retreat-Steps to the marina!
Home in Shady Side
4.96 out of 5 average rating, 56 reviewsWaterfront Sanctuary only 50 Min. From DC/Balt.
Private house rentals
Home in Deale
4.99 out of 5 average rating, 83 reviews8 Acre Pet-Friendly, Waterfront Oasis ! 140ft Pier
Home in Shady Side
5.0 out of 5 average rating, 19 reviewsPeaceful Waterfront Getaway
Home in North Beach
5.0 out of 5 average rating, 98 reviewsWaterfront, Dog-friendly, Hot Tub, Peleton, Bikes
Home in Harwood
4.97 out of 5 average rating, 29 reviewsQuiet Farm Stay near Annapolis
Home in Deale
4.95 out of 5 average rating, 21 reviewsChesapeake Paradise House-Stunning 6+br4ba Wtrfrnt
Home in Deale
5.0 out of 5 average rating, 8 reviewsQuiet Getaway in Waterfront Community
Home in Edgewater
5.0 out of 5 average rating, 49 reviewsWaterfront South River Charm Edgewater Beach Views
Home in North Beach
4.97 out of 5 average rating, 62 reviewsCharming Herrington / Rose Haven Cottage
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
$90 before taxes and fees
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