Vacation rentals in Shady Side

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Top-rated vacation rentals in Shady Side

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost

Home in Shady Side

4.88 out of 5 average rating, 174 reviews

Cattail Landing- Photographer's Waterfront Retreat

"Cattail Landing" Spring is here, with longer days, new leaves on the trees, and birds migrating back to the Bay. Take a kayak out after breakfast to explore, or go fishing off our landing. In the afternoon enjoy the magnificent sunsets, a drink on the deck, our outdoor hot tub and/or fireplace. A waterfront retreat on 2 acre in a spacious, charming house on the Western Shore of the Chesapeake Bay. Great for a couples getaway, family reunion, or work from home (w. 1GB hi-speed internet).

Jul 26 – Aug 2

R6,846 ZAR per night
Guest favorite

Cottage in Edgewater

4.99 out of 5 average rating, 123 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.

Jan 21 – 28

R6,084 ZAR per night
Guest favorite

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!

Sep 11 – 18

R8,283 ZAR per night

Popular amenities for Shady Side vacation rentals

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 vacation rentals in Shady Side

Guest favorite

Cottage in North Beach

4.96 out of 5 average rating, 268 reviews

Waterfront Cottage Near Herrington and North Beach

May 1 – 8

R3,688 ZAR per night
Guest favorite

Home in Deale

4.98 out of 5 average rating, 111 reviews

Chesapeake Waterfront-Hot Tub-Kayaks-King Bed

Apr 8 – 15

R7,035 ZAR per night
Guest favorite

Apartment in Edgewater

4.92 out of 5 average rating, 396 reviews

Pet Friendly Garden Apartment Near Annapolis

Jun 29 – Jul 6

R2,488 ZAR per night
Guest favorite

Guesthouse in Annapolis

4.97 out of 5 average rating, 152 reviews

Lil’ House - A Serene Tiny Home Experience

Jul 27 – Aug 3

R2,707 ZAR per night
Guest favorite

Home in Shady Side

4.97 out of 5 average rating, 64 reviews

Canary Pointe-A popular getaway for 2!

Nov 16 – 23

R3,260 ZAR per night
Guest favorite

Home in Shady Side

5.0 out of 5 average rating, 16 reviews

The Cottage

Apr 26 – May 3

R5,556 ZAR per night
Guest favorite

Home in Shady Side

4.91 out of 5 average rating, 22 reviews

Baydream Believer -Chesapeake Bay water community

Dec 17 – 24

R4,299 ZAR per night
Superhost

Home in Shady Side

4.87 out of 5 average rating, 23 reviews

Cozy Bay home w/180 degree view

Oct 13 – 20

R4,945 ZAR per night
Guest favorite

Cottage in Shady Side

5.0 out of 5 average rating, 9 reviews

Tranquil Waterfront Cottage - 50 minutes to DC

Aug 10 – 17

R6,744 ZAR per night
Guest favorite

Home in Shady Side

4.97 out of 5 average rating, 39 reviews

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

Jun 18 – 25

R9,611 ZAR per night
Guest favorite

Cottage in Shady Side

4.88 out of 5 average rating, 26 reviews

Luxe Chesapeake Cabin * River View* Fire Pit*

Sep 6 – 13

R5,650 ZAR per night
Guest favorite

Home in Shady Side

4.96 out of 5 average rating, 52 reviews

Waterfront Sanctuary only 50 Min. From DC/Balt.

Oct 4 – 11

R12,213 ZAR per night

Quick stats about vacation 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

R1,517 ZAR before taxes and fees

Frequently Asked Questions

  • How much does it cost to stay in house rentals in Shady Side?

    Experience the best of Shady Side with our house rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Shady Side?

    Four-legged friends are welcome in Shady Side. Choose from more than 10 vacation rentals for guests traveling with pets.

  • What are the most popular amenities for House Rentals in Shady Side?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with free parking, over 20 homes with air conditioning, over 20 homes with a kitchen, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Shady Side have a kitchen?

    Absolutely! We offer over 20 house rentals with a kitchen in Shady Side. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Shady Side have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Shady Side. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Shady Side?

    Yes! Work meets play with ease at over 20 vacation rentals in Shady Side featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Shady Side have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Shady Side. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Shady Side have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Shady Side. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore