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Monthly Rentals in Winchester

Feel at home in places that are perfect 
for staying a month or longer

Nearby monthly rentals

Home in Winchester
Bluegrass Bungalow 3 Bedroom Home
G$282,354 GYD per month
Guesthouse in Winchester
Carriage House on the Park
G$228,978 GYD per month
SUPERHOST
Home in Winchester
Cozy Cottage
G$305,248 GYD per month
SUPERHOST
Guesthouse in Winchester
Escape and unwind in the country
G$376,791 GYD per month
SUPERHOST

Monthly Rentals on Airbnb

Comforts of home
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 longer stays 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
Working made easy - find a long term stay with high-speed wifi and dedicated working spaces.
Looking for corporate housing?
Airbnb has move-in ready apartment homes ideal for staffing, displacement, and relocation needs.

Get the comforts of home and great rates for your monthly rental

  • Room for everyone
  • On-the-move workers
  • Peaceful escapes
  • Pet friendly

Stay near Winchester's top sights

Photo of Winchester Peddlers Mall
Winchester Peddlers Mall3 locals recommend
Photo of Kroger
Kroger3 locals recommend
Photo of Blue Isle Home-Style Restaurant and Bar
Blue Isle Home-Style Restaurant and Bar4 locals recommend
Photo of Engine House Pizza Pub
Engine House Pizza Pub9 locals recommend
Photo of The Daily Grind
The Daily Grind4 locals recommend
Photo of Legacy Grove Park
Legacy Grove Park4 locals recommend
*Some exclusions may apply in certain geographies and for some properties.
  1. Airbnb
  2. Monthly Rentals
  3. United States
  4. Kentucky
  5. Clark County
  6. Winchester