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, 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 favorite
Home in Shady Side
4.98 out of 5 average rating, 55 reviews

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

RandiRating, 5 stars2 months ago
Very beautiful place and super friendly host! I will be visiting again if available! So peaceful and the home is beautiful.
Top guest favorite
Home in Shady Side
4.97 out of 5 average rating, 156 reviews

Canary Pointe-A popular getaway for 2!

MaureenRating, 5 stars6 days ago
My husband and I really enjoyed our stay here! The house was very clean and was stocked with bedding, towels, toiletries, and kitchen supplies. It was also decorated so beautifully, and the bed was so comfortable! We enjoyed the nearby hiking trails, visiting Annapolis, and great seafood! Thank you Diana and Kirk for a great place to unwind an relax!
Guest favorite
Guesthouse in Galesville
4.95 out of 5 average rating, 170 reviews

Nautical Charm and relaxing waterview!

LeeRating, 5 stars5 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.

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.