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 stars1 week 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!
Guest favorite
Apartment in Arlington
4.98 out of 5 average rating, 192 reviews

Lakeside apartment, patio, hot tub, outside shower

KrystalRating, 5 stars3 months ago
Doug and Hope were fantastic hosts. Very friendly and willing to help with anything I may have needed. I especially appreciated the extra attention they put into welcoming us by giving a small welcome gift and note. You can tell they pay attention to the details. The property is beautiful as well! Loved our time there.
Guest favorite
Apartment in Arlington
4.94 out of 5 average rating, 17 reviews

Cute Accessible Studio: No stairs, W/D, Parking

CatherineRating, 5 stars1 month ago
The studio apartment is conveniently located with a Dunkin Donuts across the street. It has a comfortable bed and a good heating system to handle cold nighttime temperatures outside. Although there are other units in the same building, the studio is a quiet space at the back. And there are no stairs, as promised.
Guest favorite
Guest suite in Burlington
4.97 out of 5 average rating, 32 reviews

Stay a While, Studio Apartment-Pet Friendly

AmandaRating, 5 stars5 months ago
A lovely stay! The place was exactly as described and I always appreciate when I can bring my dogs with me. Daniella was very responsive and helpful with anything I asked. Would definitely stay again

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.
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