Monthly Rentals in Winchester
Discover long-term rentals that feel like home for stays of a month or longer.
Nearby monthly rentals
Guest favorite
Apartment in Winchester
4.78 out of 5 average rating, 111 reviewsYellow Submarine trendy basement apt w/courtyard
Oct 10 – Nov 7
$1,610 per month
Guest favorite
Townhouse in Winchester
4.95 out of 5 average rating, 169 reviewsModern Elegance in Historic Old Town Winchester
Oct 26 – Nov 23
$2,380 per month
Guest favorite
Home in Winchester
4.97 out of 5 average rating, 212 reviewsCity Charmer minutes from Old Town
Jan 3 – 31
$2,145 per month
Guest favorite
Home in Winchester
4.97 out of 5 average rating, 165 reviewsCameron Charmer pristine w/double master suites
Dec 21 – Jan 18
$2,379 per month
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.*
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.
Popular amenities for monthly rentals
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*Some exclusions may apply in certain geographies and for some properties.