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.

Guest favourite

Cottage in Edgewater

4.99 out of 5 average rating, 122 reviews

Waterfront 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

$627 NZD per night
Guest favourite

Home in Shady Side

5.0 out of 5 average rating, 113 reviews

Luxe 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

$967 NZD per night
Guest favourite

Apartment in North Beach

4.97 out of 5 average rating, 100 reviews

Bayside 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

$244 NZD per night

Popular amenities for Shady Side accommodation

Stay near Shady Side's top sights

Pirates Cove Restaurant and Dock Bar44 locals recommend
Stan and Joes Riverside20 locals recommend
Christopher's Fine Foods30 locals recommend
JesseJay's Latin Inspired Kitchen16 locals recommend
Drift Wood Diner8 locals recommend
West River pit bbq4 locals recommend

Other great accommodation in Shady Side

Guest favourite

Home in Deale

4.98 out of 5 average rating, 111 reviews

Chesapeake Waterfront-Hot Tub-Kayaks-King Bed

8–15 Apr

$761 NZD per night
Guest favourite

Cottage in North Beach

4.96 out of 5 average rating, 268 reviews

Waterfront Cottage Near Herrington and North Beach

1–8 May

$404 NZD per night
Guest favourite

Guesthouse in Annapolis

4.97 out of 5 average rating, 152 reviews

Lil’ House - A Serene Tiny Home Experience

21–28 Jul

$277 NZD per night
Guest favourite

Apartment in Deale

4.91 out of 5 average rating, 614 reviews

Romantic Wtrfrnt Flat+Solarium@Chesapeake Paradise

21–28 Mar

$421 NZD per night
Guest favourite

Home in Shady Side

4.97 out of 5 average rating, 64 reviews

Canary Pointe-A popular getaway for 2!

22–29 Dec

$342 NZD per night
Guest favourite

Home in Shady Side

5.0 out of 5 average rating, 16 reviews

The Cottage

25 Apr – 2 May

$575 NZD per night
Guest favourite

Home in Shady Side

4.91 out of 5 average rating, 22 reviews

Baydream Believer -Chesapeake Bay water community

17–24 Dec

$478 NZD per night
Superhost

Home in Shady Side

4.87 out of 5 average rating, 23 reviews

Cozy Bay home w/180 degree view

14–21 Jun

$541 NZD per night
Guest favourite

Cottage in Shady Side

5.0 out of 5 average rating, 9 reviews

Tranquil Waterfront Cottage - 50 minutes to DC

28 Apr – 5 May

$710 NZD per night
Guest favourite

Home in Shady Side

4.97 out of 5 average rating, 39 reviews

"Pier Joy!" - 3BR Waterfront Home W/Private Dock

18–25 Jun

$1,004 NZD per night
Guest favourite

Cottage in Shady Side

4.88 out of 5 average rating, 26 reviews

Luxe Chesapeake Cabin * River View* Fire Pit*

2–9 Oct

$579 NZD per night
Guest favourite

Home in Shady Side

4.96 out of 5 average rating, 52 reviews

Waterfront Sanctuary only 50 Min. From DC/Balt.

12–19 Dec

$1,272 NZD per night

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

Destinations to explore