Monthly Rentals in Chester

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.

Top Guest favourite
Home in Chester
5 out of 5 average rating, 34 reviews

Cozy 1850 farmhouse in Stone Village of Chester

Kristopher (& Kay)Rating, 5 stars1 month ago
Truly a historic home and a very nice place to stay in the area. Exceptionally well supplied for preparing meals! A big plus for us as we don’t like to eat every meal out. Communicative hosts and pleasant environment, I recommend this location to folks visiting the area!
Guest favourite
Apartment in Town of Rockingham
4.91 out of 5 average rating, 77 reviews

Lovely light-filled 2 bedroom flat

PremRating, 5 stars7 months ago
We really enjoyed our stay at Kristen’s place in Rockingham. Location was perfect, very quiet at night and very easy to walk into the little town of Bellows Falls. The bed was comfortable and the apartment was very spacious. We would highly recommend and definitely return.
Guest favourite
Home in Chester
4.95 out of 5 average rating, 42 reviews

Beautiful farmhouse in Historic village

LaineRating, 5 stars3 months ago
This was a great place to stay for skiing at Okemo! The house is so spacious, has enough room for everyone! We loved the large dining table for dinners. Would stay here again!
Top Guest favourite
Home in Chester
5 out of 5 average rating, 23 reviews

Vermont Charm in the 1840 Gideon Lee House

MarionRating, 5 stars5 months ago
Our stay in Chester was fabulous and just what we wanted. It was the perfect combination of relaxing and exploring. Polly and Ian's house is amazing! So beautiful and very nicely decorated. It's a cozy and comfortable place to unwind. The home was immaculate, and the beds were very comfortable. It was a great weekend!

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.

Stay near Chester's top sights

MacLaomainn's Scottish Pub31 locals recommend
Stone House Antique Center30 locals recommend
Country Girl Diner29 locals recommend
The Pizza Stone VT.26 locals recommend
Lisai's Chester Market Inc17 locals recommend
Stone Hearth Inn & Tavern18 locals recommend

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.
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  2. United States
  3. Vermont
  4. Windsor County
  5. Chester
  6. Monthly Rentals