Monthly Rentals in Chestertown

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

Nearby monthly rentals

Enter dates and number of guests to see the total trip price including additional fees and taxes, and rounded up to the nearest integer.

Superhost
Home in Chestertown
5 out of 5 average rating, 3 reviews

Big Bear Lodge

JaronRating, 5 stars2 weeks ago
Really cool place. Beside a little tavern. Extremely quiet at night time, in the mountains and by a lake. Place was immaculate. Great host, good communication.
Top Guest favourite
Home in Chestertown
4.95 out of 5 average rating, 234 reviews

Adirondack Lake House

MichaelRating, 5 starstoday
We came up here for a friend's wedding. the location was perfect only 5 minutes away from where we had to go. your in the woods but not too far from town if you need to make a quick run to Tops Markets. Jolanda was very responsive, but we alsp didn't need anything or had any issues. only wish we were not too busy with the wedding and could enjoy the house and property more.
Superhost
Cottage in Chestertown
4.84 out of 5 average rating, 31 reviews

Friends Lake Adirondack Cottage

NicholasRating, 5 stars9 months ago
We enjoyed our stay, the cabin was as described and met our expectations. It was a plus having utensils, pots, pans, and plates provided for use, along with towels for the shower. We would definitely stay there again!
Guest favourite
Home in Chestertown
4.9 out of 5 average rating, 29 reviews

Chestertown Charm close to Gore Mt. Come ski!

CatherineRating, 5 stars3 weeks ago
We came up for a Memorial service for a cousin who lived in Chestertown. We found the property that suited our needs and was close to where we were going to be for the 2 nights we were staying. Upon arrival the property was neat and super clean and smelled nice which was important to us. We had a small issue and called the owner and it was corrected right away, which was greatly appreciated. If I ever come back to this area I would stay in the same house as it was perfect Thank you again Jeanne-Marie for sharing your home with us and making us feel so welcome !!

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 Wi-Fi 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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