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 house rentals in Shady Side
House rentals with a pool
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
22–29 Aug
Home in Kent Narrows
5.0 out of 5 average rating, 279 reviewsChester Riverfront At Kent Narrows
2–9 Nov
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
7–14 Dec
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
23–30 Nov
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
5–12 Feb
Home in Fairfax
4.96 out of 5 average rating, 145 reviews6BR Modern Home w/HEATED Pool & Screened in Porch
27 Dec – 3 Jan
Home in Annandale
4.85 out of 5 average rating, 190 reviewsLuxury HUGE 8 Bedroom Villa 15 min to DC Sleeps 27
6–13 Jan
Home in Edgewater
4.97 out of 5 average rating, 30 reviewsEntire Beach House with Pool and Hot Tub
31 Oct – 7 Nov
Weekly house rentals
Home in Cambridge
4.89 out of 5 average rating, 111 reviewsDorothy's Chesapeake Delight
19–26 Oct
Home in Silver Spring
4.99 out of 5 average rating, 153 reviewsEntire Guest Suite/Apt in Silver Spring/FDA
20–27 Jun
Home in Shady Side
4.97 out of 5 average rating, 67 reviewsCanary Pointe-A popular getaway for 2!
29 Jan – 5 Feb
Home in Shady Side
5.0 out of 5 average rating, 18 reviewsThe Cottage
16–23 Jul
Home in Shady Side
4.91 out of 5 average rating, 23 reviewsBaydream Believer -Chesapeake Bay water community
5–12 May
Home in Shady Side
4.88 out of 5 average rating, 25 reviewsCozy Bay home w/180 degree view
15–22 Mar
Home in West River
4.97 out of 5 average rating, 73 reviewsCozy waterview home in West River!
29 Oct – 5 Nov
Home in Shady Side
5.0 out of 5 average rating, 10 reviewsWaterfront Community by Bay | Sleeps 6 | Game Room
5–12 Jun
Private house rentals
Home in Shady Side
5.0 out of 5 average rating, 17 reviewsPeaceful Waterfront Getaway
11–18 Apr
Home in Deale
5.0 out of 5 average rating, 8 reviewsQuiet Getaway in Waterfront Community
18–25 Jul
Home in North Beach
5.0 out of 5 average rating, 95 reviewsWaterfront, Dog-friendly, Hot Tub, Peleton, Bikes
16–23 Aug
Home in North Beach
4.98 out of 5 average rating, 96 reviewsHuge Beach Bungalow- Yard, Beach Pass, King Beds
10–17 Oct
Home in Edgewater
4.95 out of 5 average rating, 38 reviewsRelaxing Turkey Point Retreat-Steps to the marina!
4–11 Aug
Home in Deale
4.95 out of 5 average rating, 21 reviewsChesapeake Paradise House-Stunning 6+br4ba Wtrfrnt
26 Dec – 2 Jan
Home in Harwood
4.96 out of 5 average rating, 28 reviewsQuiet Farm Stay near Annapolis
21–28 May
Home in North Beach
4.97 out of 5 average rating, 61 reviewsCharming Herrington / Rose Haven Cottage
29 Sep – 6 Oct
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
€ 84 before taxes and fees
Destinations to explore
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- Monthly Rentals Shady Side
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