Monthly Rentals in Winchester

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

Nearby monthly rentals

Guest favorite
Guesthouse in Winchester
Escape and unwind in the country
Nov 15 – Dec 13
G$434,976 GYD per month
4.98 out of 5 average rating, 170 reviews
Guest favorite
Home in Mount Sterling
THE DOLLY - Cozy, Bright Home in Historic Downtown
Dec 26 – Jan 23
G$453,503 GYD per month
4.95 out of 5 average rating, 129 reviews
Guest favorite
Home in Stanton
RRG Climbers Choice Stay-Wifi- No cleaning fee
Jan 25 – Feb 22
G$344,759 GYD per month
4.93 out of 5 average rating, 125 reviews
Guest favorite
Guesthouse in Winchester
Carriage House Gardenside
Jan 9 – Feb 6
G$210,979 GYD per month
4.98 out of 5 average rating, 47 reviews

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

Kroger3 locals recommend
Winchester Peddlers Mall3 locals recommend
Blue Isle Home-Style Restaurant and Bar3 locals recommend
Engine House Pizza Pub8 locals recommend
Malco Winchester Cinema3 locals recommend
The Daily Grind4 locals recommend
*Some exclusions may apply in certain geographies and for some properties.
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