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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.

Bungalow in Deale
Cozy waterfront getaway on the Bay
15 Apr – 13 May
Home in Shady Side
Luxe Modern Chesapeake Waterfront Oasis
3 – 31 May
Home in Shady Side
Baydream Believer -Chesapeake Bay water community
12 Feb – 11 Mar
Guest suite in Riva
Cozy one bedroom appt on the water
23 Apr – 21 May

Find monthly rentals, furnished apartments, extended stays and more | Airbnb

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