Monthly Rentals in Chesapeake Bay

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

Nearby monthly rentals

Top guest favourite
Home in Smith Island
4.89 out of 5 average rating, 72 reviews

Smith Island Yummy Artist Retreat

JenniferRating, 5 stars4 months ago
I had an incredible, incredible time at Jemma's place. She is a consummate hostess--she was responsive and welcoming even before I made the official decision to book (I sent her some queries before booking and she was so very helpful!) Once there, she was a lovely mix of warm and friendly, yet respectful of her guests' time and privacy. She even let me borrow her rain boots when I didn't pack any! I felt right at home at the house and on the island immediately... to the point that it was a little emotional leaving! I think it's worth noting (because I was concerned about this before my arrival myself, and some of the older reviews cast some doubt...): the internet at Jemma's is very fast and reliable! I depended on it for working remotely throughout my whole stay, and it never failed me throughout zoom meetings, webinar streams, etc. I would highly recommend this beautiful home to anyone!!
Guest favourite
Guest suite in Crisfield
4.75 out of 5 average rating, 203 reviews

The Serenity House

ByronRating, 5 stars2 weeks ago
Very quaint, peacful and relaxing. Strange lay out, floor plan but it works. Good location. Quiet pretty, historic town.
Top guest favourite
Guest suite in Hebron
4.99 out of 5 average rating, 71 reviews

Comfortable, private country stay

KateRating, 5 stars3 weeks ago
We had an amazing stay here! Terri is so friendly, accommodating, and welcoming. This is one of the cleanest Airbnbs we have stayed at. It’s quiet, beautiful and had everything we needed. Highly recommend.
Top guest favourite
Tiny homes in Saint Inigoes
4.98 out of 5 average rating, 336 reviews

Historic St.Mary's City at the Lazy Bear Cottage

SarahRating, 5 stars1 week ago
We alerted Nancy of our late check in due to travel and she was so caring and thoughtful to make sure we found the place. How wonderful to check in and find an emasculate and more than comfortable place to rest our heads after a long travel day! Our fur baby felt more than loved with a special Love note waiting for him on the table and treats - and human treats as a surprise for us in the fridge!! We stayed each day with peace and coffee on the dock!! We felt so welcomed and cared for and appreciated it so much!

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

Travelling 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.