
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, 117 reviewsWow! 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 favorite

Cottage in Sheffield
4.87 out of 5 average rating, 75 reviewsCharming 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 favorite

Apartment in Sheffield
5 out of 5 average rating, 358 reviewsHideaway 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 reviewsBull 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.
The comforts of home and great monthly rates
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.*
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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.
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*Some exclusions may apply in certain geographies and for some properties.