Vacation rentals in Shady Side
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Top-rated accommodation in Shady Side
Guests agree: these stays are highly rated for location, cleanliness and more.
Cottage in Edgewater
4.99 out of 5 average rating, 122 reviewsWaterfront Chesapeake Bay Getaway Firepit & Pier!
Gorgeous sunrises from your completely remodeled waterfront cottage! Experience fresh Maryland Crabs or fish caught from your private pier & enjoy the peace, serenity and bay breezes from your furnished deck and green space. Enjoy true nature and explore Selby Bay on the South River with our complimentary canoe! Super clean with water views from kitchen, dining, living room & enclosed porch! Situated in a quiet neighborhood within 45 minutes of DC & 15 minutes from Annapolis & the Naval Academy.
11–18 Nov
Home in Shady Side
5.0 out of 5 average rating, 113 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
The Cottage at Silverwater is a lesson in quiet luxury, compelling architecture, unimaginable views and endless comforts. Original fine art and luxe bedding envelope you in a modern, light-filled space. Outside you will be treated to an expansive waterfront lawn that is great for games and afternoon sun. Rest on modern lounges or watch the sunset on your private waterfront bluestone patio tucked into the sea grass. As a guest favorite, your fabulous getaway is here—just read the reviews!
18–25 Mar
Apartment in North Beach
4.97 out of 5 average rating, 100 reviewsBayside Oasis of Southern Maryland
1 1/2 blocks from the beautiful Chesapeake Bay. Walk to boardwalk, restaurants and shopping. Beach opens, with some restrictions, May 28, 2021. Free beach pass provided. Quiet friendly town where everyone knows your name. King bed, private bath with shower (no tub). Free WiFi, private off street parking, 45” TCL-Roku TV, Echo Dot, Keurig w/pods for coffee and tea, full kitchen (no dishwasher), beach chairs, beach towels, dishes, flatware, pots pans. Chesapeake Beach is 1-mile south on Rt 262.
4–11 Nov
Accommodation for every style
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Popular amenities for Shady Side accommodation
Other great accommodation in Shady Side
Home in Deale
4.98 out of 5 average rating, 111 reviewsChesapeake Waterfront-Hot Tub-Kayaks-King Bed
8–15 Apr
Cottage in North Beach
4.96 out of 5 average rating, 268 reviewsWaterfront Cottage Near Herrington and North Beach
1–8 May
Guesthouse in Annapolis
4.97 out of 5 average rating, 152 reviewsLil’ House - A Serene Tiny Home Experience
21–28 Jul
Apartment in Deale
4.91 out of 5 average rating, 614 reviewsRomantic Wtrfrnt Flat+Solarium@Chesapeake Paradise
21–28 Mar
Home in Shady Side
4.97 out of 5 average rating, 64 reviewsCanary Pointe-A popular getaway for 2!
22–29 Dec
Home in Shady Side
5.0 out of 5 average rating, 16 reviewsThe Cottage
25 Apr – 2 May
Home in Shady Side
4.91 out of 5 average rating, 22 reviewsBaydream Believer -Chesapeake Bay water community
17–24 Dec
Home in Shady Side
4.87 out of 5 average rating, 23 reviewsCozy Bay home w/180 degree view
14–21 Jun
Cottage in Shady Side
5.0 out of 5 average rating, 9 reviewsTranquil Waterfront Cottage - 50 minutes to DC
28 Apr – 5 May
Home in Shady Side
4.97 out of 5 average rating, 39 reviews"Pier Joy!" - 3BR Waterfront Home W/Private Dock
18–25 Jun
Cottage in Shady Side
4.88 out of 5 average rating, 26 reviewsLuxe Chesapeake Cabin * River View* Fire Pit*
2–9 Oct
Home in Shady Side
4.96 out of 5 average rating, 52 reviewsWaterfront Sanctuary only 50 Min. From DC/Balt.
12–19 Dec
Quick stats about holiday rentals in Shady Side
Total rentals | 30 properties |
---|---|
Rentals with dedicated workspaces | 20 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 | 940 reviews |
Nightly prices starting at | $133 NZD before taxes and fees |
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