Airbnb your place

Vacation rentals in Shady Side

Find and book unique accommodations on Airbnb

When results are available, navigate with up and down arrow keys or explore by touch or swipe gestures.
0 of 0 items showing
1 of 3 pages

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Shady Side vacation rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Stay near Shady Side's top sights

Pirates Cove Restaurant and Dock Bar44 locals recommend
Christopher's Fine Foods30 locals recommend
Stan and Joes Riverside20 locals recommend
JesseJay's Latin Inspired Kitchen16 locals recommend
Captain Salem Avery Museum8 locals recommend
Drift Wood Diner8 locals recommend

Other great vacation rentals in Shady Side

Guest favorite

Home in West River

4.98 out of 5 average rating, 98 reviews

Cozy waterview home in West River!

Guest favorite

Home in Shady Side

5 out of 5 average rating, 25 reviews

Peaceful Waterfront Getaway

Guest favorite

Rental unit in North Beach

4.97 out of 5 average rating, 122 reviews

Bayside Oasis of Southern Maryland

Guest favorite

Home in Shady Side

4.93 out of 5 average rating, 41 reviews

Cozy Bay home w/180 degree view

Guest favorite

Guesthouse in Edgewater

4.99 out of 5 average rating, 85 reviews

1 large room efficiency in detached garage.

Superhost

Home in Shady Side

4.89 out of 5 average rating, 27 reviews

Chesapeake Peace

Guest favorite

Home in Shady Side

4.83 out of 5 average rating, 12 reviews

Chesapeake Bay - West River Home

Guest favorite

Home in Shady Side

4.98 out of 5 average rating, 53 reviews

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

Show all

Quick stats about vacation rentals in Shady Side

  • Total rentals

    30 properties

  • Nightly prices starting at

    $90 before taxes and fees

  • Total number of reviews

    1.3K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

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 $90 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 wifi, over 20 homes with free parking, over 20 homes with a kitchen, over 20 homes with air conditioning, 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