Monthly Rentals in Shady Side

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

Nearby monthly rentals

Guest favorite
Home in Shady Side
4.96 out of 5 average rating, 106 reviews

Waterfront w/ Private Pier, 35 Mins to Annapolis

NicholasRating, 5 stars7 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 favorite
Home in Shady Side
4.98 out of 5 average rating, 173 reviews

Canary Pointe-A popular getaway for 2!

AbigailRating, 5 stars1 week ago
This Airbnb was amazing!! Honestly even cuter in person compared to the photos! I would recommend this spot to anyone visiting the area!! 10/10 experience!
Guest favorite
Home in Shady Side
4.96 out of 5 average rating, 85 reviews

Waterfront Sanctuary only 50 Min. From DC/Balt.

LaurenRating, 5 stars1 week ago
We had a wonderful stay here! The location and setup was perfect for our multi generational family gathering. The level of detail and thought that was put into the amenities and setup was exceptional. The recommendations provided made planning our trip so easy. The kids (toddler to preteen) had a ton to do when the weather interrupted planned outdoor activities. The views were impressive. Marc was responsive when any questions came up. We all hope to return!
Guest favorite
Guesthouse in Lyon Village
4.95 out of 5 average rating, 170 reviews

Nautical Charm and relaxing waterview!

LeeRating, 5 stars7 months ago
I stayed here visiting family nearby. The place is very clean and set up thoughtfully for guests. I really appreciated that it was already stocked with some coffee and creamers, so I didn't need to go shopping right after arriving. The neighborhood is small but walkable and has two good seafood restaurants a short walk away. Pam provided clear instructions and communication.

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 vacation 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

Traveling professional? Find a long-term stay with high-speed wifi and dedicated working spaces.

Looking for corporate housing?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing, and relocation needs.
*Some exclusions may apply in certain geographies and for some properties.