Monthly Rentals in Chester

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

Nearby monthly rentals

Top guest favorite
Farm stay in Worthington
4.97 out of 5 average rating, 31 reviews

Like sleeping on a cloud

ChristineRating, 5 stars1 week ago
The farm is a beautiful, inspiring getaway. It’s the perfect balance of dreamy farmhouse, outdoor grandeur, utility, and no clutter. Our toddler felt right at home, too! If you find yourself thinking about a life in the hill towns (and you might!), there is a rich library of the history, landscape, and farming & conservation techniques of the area. Kim is friendly and responsive and everything is clean and comfortable. Would definitely stay again!
Top guest favorite
Cabin in Cummington
4.98 out of 5 average rating, 212 reviews

Just Be Cabin

MelindaRating, 5 stars3 weeks ago
Enjoyed our stay at the cabin, very nice little weekend getaway and stayed cozy during the surprise late winter wonderland. Stacey keeps the place well equipped and looking very nice for a cabin!
Guest favorite
Home in Becket
4.96 out of 5 average rating, 73 reviews

Nerd Preservation Sanctuary

ChelseaRating, 5 stars2 months ago
The hosts exceed superhosts-communicative, friendly, care about their visitors’ stay and know their property very well. The house if funky original and shows off the owners’ personalities in a fun way. Listing is perfect and has all listed amenities. Thanks T & B. You both are rockstars.
Guest favorite
Cottage in Becket
4.95 out of 5 average rating, 273 reviews

Berkshires Cottage by Lake. Year Round Adventures.

ElanaRating, 5 stars2 months ago
loved this cozy cabin for a snowed in weekend. the setting is beautiful and the house is completely stocked with everything you could need for quiet time with family. we came with two small kids and it was well suited for them. hoping to come back in the summer to enjoy the lake. thanks Scott for being such a phenomenal and responsive host amid the crazy snow storm.

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.

Stay near Chester's top sights

Chester Common Table4 locals recommend
Keystone Arch Bridges Trail3 locals recommend
Carm’s Restaurant and Coffee Shop5 locals recommend
*Some exclusions may apply in certain geographies and for some properties.