Monthly Rentals in Winchester

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

Nearby monthly rentals

Top guest favorite
Cottage in Winchester
4.95 out of 5 average rating, 66 reviews

The Little House - a Historic New England cottage

AdamRating, 5 stars2 weeks ago
The Little House was very cleaned and had everything needed for a comfortable stay. I was in town for work and the house's cozy atmosphere and view of the pond made it a great place to unwind and relax at the end of a long work day. I felt right at home. I would love to return on future business trips and it would be great to stay sometime for a more leisurely vacation. Highly recommend!
Home in Winchester
4.59 out of 5 average rating, 27 reviews

House on A+ school area w/AC & W/D

SalmaRating, 5 stars8 months ago
Thank you jess for making our stay in Boston flawless! We were so lucky to be hosted by you. Place is very clean and we had everything we needed, area is very safe sometimes we slept without locking the door! That is a highly recommended place and once again thank you jess for being a sweetheart!❤️❤️❤️
Guest favorite
Guest suite in Burlington
4.97 out of 5 average rating, 33 reviews

Stay a While, Studio Apartment-Pet Friendly

MaryRating, 5 stars2 weeks ago
Daniella's place was perfect for my needs. I spent two months in the area to help out family, and this studio was a cozy place to rest, relax and cook. Plenty of restaurants and markets nearby. Handy to all that Burlington has to offer. The kitchen was clean and well equipped, living and sleeping space cozy and comfortable. Walk in closet with room to store everything I had with me. Even though this apartment is attached to the house, it was very quiet and felt completely private. I will definitely stay here again!
Guest favorite
Home in Woburn
4.96 out of 5 average rating, 117 reviews

Stone Cottage with meadow view

ChristopherRating, 5 stars1 week ago
This beautiful home is all you could ask for in a peaceful getaway. Every room was immaculate. Warm and inviting, it felt like home from the moment we walked in the door. Lauren's proactive communication put us at ease before we even arrived. Detailed entry instructions (with pictures!) made sure this was a stress-free process every step of the way. Every room was spotless and cozy. The pictures capture the rooms accurately, but they could d never show the hundreds of thoughtful touches that make this feel like home away from home. We loved the layout and only wish we had more time there. Whether watching a movie by the fireplace or eating dinner in the dinning room, this place was perfection. We spent a day in Concord and days in Boston and this location is ideally situated to explore both. If we're ever back in the area, we would love to go back. Thank you Lauren for sharing your lovely home with us!

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 Winchester's top sights

Whole Foods Market149 locals recommend
Horn Pond10 locals recommend
Lord Hobo Brewing Company7 locals recommend
D'Agostino's Delicatessen5 locals recommend
Black Horse Tavern5 locals recommend
The Brickyard4 locals recommend
*Some exclusions may apply in certain geographies and for some properties.