Monthly Rentals in Sheffield

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

Nearby monthly rentals

Guest favorite
Home in Sheffield
4.91 out of 5 average rating, 116 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

JohannaRating, 5 stars2 months ago
We thoroughly enjoyed our stay in Sally’s cozy apartment! It is well appointed and tastefully decorated. Sally was very responsive and caring. The beautiful views out of our bedrooms onto the garden and the wide open landscape behind it were major treats, especially on the morning after a heavy snowfall. We found everything we needed and more than expected - and hope to be back one day! Thank you very much, Sally!
Guest favorite
Cottage in Sheffield
4.86 out of 5 average rating, 71 reviews

Charming Handcrafted Cottage in the Berkshires!

JakeRating, 5 stars5 days ago
House was as expected in a private location close to Great Barrington. The reading nook and comfortable beds were really nice highlights that stood out. Josh and Kelly were very responsive, and offered some great recommendations.
Top guest favorite
Apartment in Sheffield
5 out of 5 average rating, 354 reviews

Hideaway with Spectacular Berkshire Views

StaceyRating, 5 stars1 month ago
Lovely space. Books and decor made the space welcoming, but remained open and uncluttered. Everything was seemed quite new and was very clean. Area surrounding the apartment is peaceful, unit was very quiet, and heated efficiently even during our cold February stay.
Guest favorite
Cottage in Great Barrington
4.91 out of 5 average rating, 247 reviews

Cottage on Scenic Road

AyeshaRating, 5 stars2 months ago
Charming and warm cottage, sweet layout. 5 min from town, 5 min from the Appalachian trail and other hikes. About an hour from MASS MOCA and the Clarke. The stove fire is lovely- nice place to come back to. Seamus was responsive and accommodating.

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 Sheffield's top sights

Old Mill73 locals recommend
The Barn50 locals recommend
Bartholomew's Cobble Reservation45 locals recommend
Berkshire Mountain Distillers34 locals recommend
Big Elm Brewing31 locals recommend
The Stagecoach Tavern26 locals recommend

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.