Monthly Rentals in Fairlee

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

Nearby monthly rentals

Superhost
Cottage in Chestertown
4.91 out of 5 average rating, 35 reviews

Chesapeake East Shore Chestertown,Pool (May1),Dock

AntoinetteRating, 5 stars8 months ago
We loved our stay at the cottage. Everything was clean and well maintained inside and out. We especially loved the gorgeous surroundings. The property was beautiful and peaceful. We enjoyed daily swims in the pool and time at the dock. Robert was a wonderful host and made everything very clear and easy as well as was easy to communicate with. We couldn't have asked for a better get away. Chestertown is adorable and fun to check out. We hope to return in the future.
Guest favourite
Home in Rock Hall
5 out of 5 average rating, 126 reviews

Bayside Beach House

JanaRating, 5 stars2 weeks ago
Perfect little house for a relaxing stay in Rock Hall. Close to the water and a quiet neighborhood perfect for walking in the morning or evening. Melissa sent so many great recommendations - great host!
Top guest favourite
Guest suite in Chestertown
4.99 out of 5 average rating, 221 reviews

Beautiful Waterfront Chestertown Getaway

JennRating, 5 stars1 week ago
My husband and I along with our dog Cash had a wonderful stay at Tom and Jen's place. It was very spacious and the view was spectacular. The fenced in yard was great for our dog who loved meeting and playing with their dog. Tom and Jen chatted with us when we first arrived and made us feel very welcome. The neighborhood was very peaceful and we really enjoyed taking our dog for walks during our visit. Everything was perfect! We would love to stay there again next time we're in Chestertown.
Top guest favourite
Barn in Chestertown
5 out of 5 average rating, 29 reviews

"The Barn" unique design, farm views, beach access

JuliaRating, 5 stars2 weeks ago
My friends and I had such a nice getaway weekend at the Barn. The house has such a unique charm, and is the perfect spot to unwind with a book, cup of coffee, and a blanket. Our group did a pirate murder mystery dinner together one night at the Barn and the wood paneling & beams, "crows nest" turret, and vaulted ceilings worked great with the theme! We enjoyed spending mornings working on a puzzle over coffee and watching the cardinals outside the dining room windows. Hannah was very communicative and responsive. 10/10 Airbnb!

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 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.
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