Skip to content

Monthly Rentals in Chestertown

Feel at home in places that are perfect for staying a month or longer

Nearby monthly rentals

Rental unit in Chestertown
Secluded Cottage in Middle of Chestertown
Individual Host
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
Individual Host
Guest house in Chestertown
Cozy Carriage House
Individual Host
Private room in Chestertown
Perfect Long Term Rental

Monthly Rentals on Airbnb

Comforts of home

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 longer stays 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

Working made easy – find a long term stay with high-speed wifi and dedicated working spaces.

Looking for corporate housing?

Airbnb has move-in ready apartment homes ideal for staffing, displacement, and relocation needs.

Stay near Chestertown's top sights

Photo of Fish Whistle
Fish Whistle23 locals recommend
Photo of Luisa's Cucina Italiana
Luisa's Cucina Italiana27 locals recommend
Photo of Procolino's Pizza
Procolino's Pizza15 locals recommend
Photo of ACME Markets
ACME Markets13 locals recommend
Photo of 98 Cannon Riverfront Grille
98 Cannon Riverfront Grille11 locals recommend
Photo of Wilmer Park
Wilmer Park4 locals recommend
*Some exclusions may apply in certain geographies and for some properties.
  1. Airbnb
  2. Monthly Rentals
  3. United States
  4. Maryland
  5. Kent County
  6. Chestertown