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.
Home in Shady Side
4.88 out of 5 average rating, 174 reviewsCattail 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
Cottage in Edgewater
4.99 out of 5 average rating, 123 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.
Jan 21 – 28
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!
Sep 11 – 18
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Shady Side vacation rentals
Other great vacation rentals in Shady Side
Cottage in North Beach
4.96 out of 5 average rating, 268 reviewsWaterfront Cottage Near Herrington and North Beach
May 1 – 8
Home in Deale
4.98 out of 5 average rating, 111 reviewsChesapeake Waterfront-Hot Tub-Kayaks-King Bed
Apr 8 – 15
Apartment in Edgewater
4.92 out of 5 average rating, 396 reviewsPet Friendly Garden Apartment Near Annapolis
Jun 29 – Jul 6
Guesthouse in Annapolis
4.97 out of 5 average rating, 152 reviewsLil’ House - A Serene Tiny Home Experience
Jul 27 – Aug 3
Home in Shady Side
4.97 out of 5 average rating, 64 reviewsCanary Pointe-A popular getaway for 2!
Nov 16 – 23
Home in Shady Side
5.0 out of 5 average rating, 16 reviewsThe Cottage
Apr 26 – May 3
Home in Shady Side
4.91 out of 5 average rating, 22 reviewsBaydream Believer -Chesapeake Bay water community
Dec 17 – 24
Home in Shady Side
4.87 out of 5 average rating, 23 reviewsCozy Bay home w/180 degree view
Oct 13 – 20
Cottage in Shady Side
5.0 out of 5 average rating, 9 reviewsTranquil Waterfront Cottage - 50 minutes to DC
Aug 10 – 17
Home in Shady Side
4.97 out of 5 average rating, 39 reviews"Pier Joy!" - 3BR Waterfront Home W/Private Dock
Jun 18 – 25
Cottage in Shady Side
4.88 out of 5 average rating, 26 reviewsLuxe Chesapeake Cabin * River View* Fire Pit*
Sep 6 – 13
Home in Shady Side
4.96 out of 5 average rating, 52 reviewsWaterfront Sanctuary only 50 Min. From DC/Balt.
Oct 4 – 11
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.
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