Monthly Rentals in Fairlee

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

Nearby monthly rentals

Top guest favorite
Home in Chestertown
4.94 out of 5 average rating, 94 reviews

Simple Living on the Pond

CarverRating, 5 stars1 month ago
Lovely house in a beautiful and peaceful setting. Well equipped kitchen, bathroom and cozy, comfortable bedding and beds! I recommend Diana’s place for a peaceful and relaxing stay.
Guest favorite
Home in Chestertown
4.96 out of 5 average rating, 24 reviews

Lotus House: porches, decks, yard, beach access

ChrisRating, 5 stars3 months ago
We had a great stay here, very relaxing. The home is very comfortable. We were there in January, so we appreciated the space and comfort.
Top guest favorite
Guest suite in Chestertown
4.99 out of 5 average rating, 159 reviews

Chestertown - Eastern Shore Getaway

KeithRating, 5 stars1 week ago
This is a beautiful old house, and Jim and Gale are very welcoming hosts. The guest area is on the third floor, which means total privacy (and a little bit of exercise!). The guest area has been thoroughly remodeled, so the bathroom is new and pristine, plenty of electrical outlets. etc. The location is ideal: directly across from the Washington College campus, and about three blocks from downtown Chestertown. It's a great place to stay, I look forward to returning.
Top guest favorite
Guest suite in Chestertown
4.99 out of 5 average rating, 221 reviews

Beautiful Waterfront Chestertown Getaway

JennRating, 5 stars4 days 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.

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.
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