Monthly Rentals in Sheffield

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

Nearby monthly rentals

Top guest favorite
Guest suite in Sheffield
5 out of 5 average rating, 78 reviews

The Sunset Suite~Great South Berkshire Location!

TomRating, 5 stars3 weeks ago
We've stayed at a lot of different locations over the years and the Sunset Suite is our favorite Air B and B location by far for a lot of reasons. First, Sharon and Oliver are our favorite Air B and B hosts. We always feel right at home, they have excellent recommendations for restaurants and things to see and do including any new places since the last time we visited, and are just great people. The Sunset Suite is always super clean and comfortable and provides everything we need as our home base for Sheffield/Great Barrington adventures (and beyond). Sharon and Oliver do a great job with the property - it's very well kept and something is almost always in bloom. It's a great location to see local wildlife (lots of interesting bird species) and the general surrounding area (farms, fields, and woods) is beautiful as well. If you're looking for a clean, quiet, and comfortable location to unwind, the Sunset Suite is a fantastic location. We're looking forward to our next stay !
Guest favorite
Cottage in Sheffield
4.87 out of 5 average rating, 76 reviews

Charming Handcrafted Cottage in the Berkshires!

RubinaRating, 5 stars1 month ago
Very comfy house and felt right at home. Very clean and true to photos. . Kelly and Josh were very responsive. We did enjoy our stay!
Top guest favorite
Apartment in Sheffield
5 out of 5 average rating, 364 reviews

Hideaway with Spectacular Berkshire Views

JohnRating, 5 stars1 week ago
Nothing but good things to say about my stay. Hosts were friendly, welcoming, and responsive. Apartment was adorable, homey, and well furnished. Property was quintessential southern New England. You won’t be disappointed.
Guest favorite
Cottage in Great Barrington
4.92 out of 5 average rating, 250 reviews

Cottage on Scenic Road

JulieRating, 5 stars1 month ago
Another great stay at the little cabin "in the woods" near GB. So peaceful and quiet, but still lots to do in the area. This was our third time staying at Seamus's cabin and it was great - we even got to use the wood-burning stove since this visit was during a cooler time of year (compared to 90 degrees last September).

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.

Destinations to explore

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