Monthly Rentals in Sheffield

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.

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
Apartment in Sheffield
5 out of 5 average rating, 358 reviews

Hideaway with Spectacular Berkshire Views

BrittRating, 5 stars2 days ago
This AirBnB is an absolute dream - look no further! I lived in the Berkshires for 8 years and was back visiting friends and could not have asked for a more perfect and charming accommodation. Great location with easy access to GB, Sheffield, Lakeville, etc. Great food options, incredible hiking, and so much beauty in Ricky and Elisabeth's backyard. This will be my go-to spot in the Berkshires. I am truly sad to leave! This place is perfection and captures what the Berkshires is all about. Ricky and Elisabeth were so caring, thoughtful and kind. 10/10 recommend. A true gem!
Superhost
Home in Sheffield
4.96 out of 5 average rating, 23 reviews

Bull Hill Bungalow

DianaRating, 5 stars1 month ago
Beautiful space to cozy up and enjoy peace. I needed a mental health getaway to enjoy nature and respite from the day-to-day. The wood-burning stove was incredible, already set up with everything I needed, ready to have a fire. The fully functioning and easy-to-use kitchen was great, and there were beautiful paintings everywhere. Be mindful if you have a dog—I did see a bear down the street about a mile away, which is expected in Western Massachusetts, so keep pets leashed. As described, the house connects to an apartment on the other side, with a door leading to their porch through one bedroom, and a window in the other. Vintage cabin vibes inside. Beautiful views no matter which way you look. An enormous and diverse selection of books, old and new. I stayed one night and wish I could stay another. My lab enjoyed relaxing by the fire’s warmth. Easy to find and a short drive to nearby towns.

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 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.