Monthly Rentals in Sheffield

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

Nearby monthly rentals

Guest favourite
Home in Sheffield
4.91 out of 5 average rating, 117 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

FeliciaRating, 5 stars2 months ago
Sally responded to questions right away. She was really attentive - making sure snow was cleared and ice salted so that we could leave early in the morning after a big snow storm. The place was really conveniently located 15 minutes from ski Butternut. And it was immaculately clean and so cozy. It was a really nice stay.
Guest favourite
Cottage in Sheffield
4.87 out of 5 average rating, 75 reviews

Charming Handcrafted Cottage in the Berkshires!

JanaRating, 5 stars2 weeks ago
We chose this location as a midway point for 3 college roommates and a dog (coming from Maine, Delaware & NY) looking for a long weekend with hiking and good food! We loved the proximity to Great Barrington & Lee and all the hiking close by! We saw a bear on the property the first 2 minutes we were there which was pretty cool! Host was very responsive and helpful. We enjoyed the cozy spot in the woods! Would certainly consider again!! Thank you!!
Top guest favourite
Flat in Sheffield
5 out of 5 average rating, 357 reviews

Hideaway with Spectacular Berkshire Views

RickRating, 5 stars3 weeks ago
This is our go-to place in the Berkshires and we love everything about it. We consider it home base for exploring the area with all it has to offer. Elisabeth has made a retreat that allows us to relax and destress in a wonderful environment.
Guest favourite
Cottage in Great Barrington
4.92 out of 5 average rating, 248 reviews

Cottage on Scenic Road

DavidRating, 5 stars1 month ago
Picture the scene, crawling out of a toasty warm bed, a dusting of snow outside as you brew up a pair of espressos. The heady aroma entices my lovely bride of 27 years to poke her nose out from under the duvet. As we enjoyed our first sips we were treated to the excited chortling and gobbling of over twenty turkeys as they passed by the cabin. The peace and quiet was punctuated by the occasional woodpecker and wild turkey. We enjoyed a glass or two of wine sitting in front of the warm glow of the wood stove. Peace - quiet - nature - comfort - The Cabin gave us the pause we needed - we recommend everyone, young and old to slow down, reconnect, discover each other in this beautiful cabin in the woods!

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 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.
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