Monthly Rentals in Chestertown
Discover long-term rentals that feel like home for stays of a month or longer.
Nearby monthly rentals
Guest favorite
Home in Chestertown
4.93 out of 5 average rating, 88 reviewsSimple Living on the Pond
Guest favorite
Rental unit in Chester
4.97 out of 5 average rating, 260 reviewsCozy Waterfront Apartment Chester, MD
Guest favorite
Guest suite in Chestertown
4.96 out of 5 average rating, 68 reviewsHistoric Downtown Garden Oasis with Private Patio
Guest favorite
Guest suite in Chestertown
4.99 out of 5 average rating, 215 reviewsBeautiful Waterfront Chestertown Getaway
The comforts of home and great monthly rates
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.
Popular amenities for monthly rentals
Destinations to explore
- New York Monthly Rentals
- Barcelona Monthly Rentals
- Florence Monthly Rentals
- Athens Monthly Rentals
- Miami Monthly Rentals
- Montreal Monthly Rentals
- Seattle Monthly Rentals
- Berlin Monthly Rentals
- Paris Monthly Rentals
- Rio de Janeiro Monthly Rentals
- Amsterdam Monthly Rentals
- Istanbul Monthly Rentals
- Lisbon Monthly Rentals
- Rome Monthly Rentals
- Copenhagen Monthly Rentals
- Portland Monthly Rentals
- Buenos Aires Monthly Rentals
- Cape Town Monthly Rentals
- London Monthly Rentals
- Tokyo Monthly Rentals
- Sydney Monthly Rentals
- Austin Monthly Rentals
- Prague Monthly Rentals
- Vienna Monthly Rentals
- San Francisco Monthly Rentals
- Hamburg Monthly Rentals
- Washington DCÂ Monthly Rentals
- Vancouver Monthly Rentals
- Brussels Monthly Rentals
- Los Angeles Monthly Rentals
- Munich Monthly Rentals
- Bangkok Monthly Rentals
- Baltimore Vacation rentals
- Ocean City Vacation rentals
- Atlantic City Vacation rentals
- Cape May Vacation rentals
- Wildwood Vacation rentals
- Rehoboth Beach Vacation rentals
- Washington Vacation rentals
- Deep Creek Lake Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- The Hamptons Vacation rentals
- Monthly Rentals United States
- Monthly Rentals Philadelphia
- Monthly Rentals Baltimore
- Monthly Rentals Maryland
- Family-friendly rentals Chestertown
- Rentals with a washer and dryer Chestertown
- Rentals with a patio Chestertown
- House rentals Chestertown
- Rentals with outdoor seating Chestertown
- Monthly Rentals Kent County
*Some exclusions may apply in certain geographies and for some properties.