Monthly Rentals in Shady Side

Discover long-term rentals that feel like home, for stays of a month or longer.

Nearby monthly rentals

Enter dates and number of guests to see the total trip price including additional fees and taxes, and rounded up to the nearest integer.

Guest favourite
Home in Shady Side
4.96 out of 5 average rating, 105 reviews

Waterfront w/ Private Pier, 35 Mins to Annapolis

NicholasRating, 5 stars5 months ago
We had 6 people for a weekend retreat and this was a fantastic house and location for us. the host was super communacitive and easy/friendly to work with. We'll go back for sure next time we need a retreat space that is quiet, private and affordable.
Top Guest favourite
Home in Shady Side
4.98 out of 5 average rating, 56 reviews

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

SharonRating, 5 stars1 week ago
Pier Joy was comfortable for 5 adults. We celebrated Easter as a family and chose it for the private dock and water views. We lucked out with perfect weather. Thank you for a great place to make more fun memories with our older children.
Top Guest favourite
Home in Shady Side
4.97 out of 5 average rating, 158 reviews

Canary Pointe-A popular getaway for 2!

ChristinaRating, 5 stars1 week ago
I enjoyed my time staying at this Airbnb! The house felt right at home. The inside of the house is beautiful! I would stay here again! 100/10
Guest favourite
Home in Shady Side
4.95 out of 5 average rating, 20 reviews

Ruby Of The Bay

JulieRating, 5 stars3 weeks ago
Thank you for sharing your beautiful home! We loved the neighborhood, fenced in yard, beautiful kitchen and comfortable home. Nikki was an excellent host with great communication and very responsive. Unfortunately the weather wasn't so great so we didn't get to do much by the water. Beautiful area!

Amenities and perks for longer stays

Furnished rentals

Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.

Flexibility you need

Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*

Simple monthly prices

Special rates for long-term holiday rentals and a single monthly payment without additional charges.*

Book with confidence

Reviewed by our trusted community of guests and 24/7 support during your extended stay.

Work-friendly spaces for digital nomads

Travelling professional? Find a long-term stay with high-speed Wi-Fi and dedicated working spaces.

Looking for corporate housing?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing and relocation needs.

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
*Some exclusions may apply in certain geographies and for some properties.