Monthly Rentals in Chestertown

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

Nearby monthly rentals

Guest favourite
Home in Chestertown
4.94 out of 5 average rating, 65 reviews

Beautifully remodeled home in Historic Chestertown

LauraRating, 5 stars1 week ago
Ashli’s place was a great location for exploring Chestertown. It was an easy walk to downtown and the water. She was very responsive to all questions we had and very welcoming. The house was spotless and the beds were extremely comfortable!
Top guest favourite
Apartment in Chestertown
5 out of 5 average rating, 103 reviews

Waterfront historic district 1BR Apartment

MistyRating, 5 stars2 days ago
Super comfortable cozy apartment! We loved the local and the view. Thoughtful touches of snacks, water etc. made a nice welcome. We will definitely want to come back next year. After each evening event we said "Let's go home" doesn't get much better than that. The bed was entirely wonderful, comfortable and warm. (Not easy to find a comfortable bed when away) Thanks to our host -Misty
Top guest favourite
Guest suite in Chestertown
4.99 out of 5 average rating, 159 reviews

Chestertown - Eastern Shore Getaway

KeithRating, 5 stars2 weeks 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.
Superhost
Guesthouse in Chestertown
4.88 out of 5 average rating, 171 reviews

Cozy Carriage House

PatrickRating, 5 stars1 month ago
The property was exactly as advertised. I thoroughly enjoyed my stay. It was very quiet which I liked very much. Roland was very helpful with check in and made our stay very nice.

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.

Stay near Chestertown's top sights

Evergrain Bread Company37 locals recommend
Luisa's Cucina Italiana27 locals recommend
Play It Again Sam25 locals recommend
Chester River Wine & Cheese Co.22 locals recommend
The Kitchen at the Imperial20 locals recommend
Sultana Education Foundation17 locals recommend
*Some exclusions may apply in certain geographies and for some properties.
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