Monthly Rentals in Winchester Springs

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

Nearby monthly rentals

Guest favourite

Cottage in Iroquois

4.9 out of 5 average rating, 372 reviews

Garden Shack

EmilyRating, 5 stars1 day ago

We loved staying here! Homey, cozy, and very clean. Our kids loved the loft! Would definitely recommend :)

Top Guest favourite

Apartment in Winchester

4.94 out of 5 average rating, 201 reviews

1 bedroom furnished suite

KatieRating, 5 stars1 week ago

Myrna was a wonderful host, super responsive and very accommodating. Her space was lovely and clean. Exactly what we needed to enjoy our weekend. Would happily return for another stay!

Apartment in Williamsburg

4.7 out of 5 average rating, 106 reviews

Kim's Country Retreat

NathanaelRating, 5 starstoday

Kimberley’s place was great! It was perfect for us while visiting Upper Canada Village. My wife and I liked the bathroom. It had a nice clawfoot tub accompanied by vintage style faucets. Kimberley even provided us complimentary bath bombs. The kitchen was also fully setup with an oven, fridge, and even a big freezer. Highly recommend!

Guest favourite

Guesthouse in Newington

4.92 out of 5 average rating, 461 reviews

Trees, open spaces, and the milky way at night

AntonRating, 5 stars6 days ago

Great stay, would definitely go back! Very peaceful place if you’re looking to just hang out and relax.

Explore all

The comforts of home and great monthly rates

Fully furnished rentals

From peaceful mountain cabins to convenient urban apartments these furnished rentals have all the amenities of home.

Digital nomads & travelling professionals

Comfortable accommodation for nomadic and remote working professionals, with Wi-Fi and dedicated workspaces.

Delight included

Sometimes the destination is the accommodation. From cliffside cabins to tranquil houseboats, these rentals are full of unique features.

Pets welcome

Discover places to stay that accommodate pets, so you can bring your four-legged friend along.

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 holiday 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

Travelling professional? Find a long-term stay with high-speed Wi-Fi and dedicated working spaces.

Looking for serviced apartments?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing and relocation needs.

Popular amenities for monthly rentals

Kitchen

Wi-Fi

Pet friendly

Laptop-friendly workspace

Free parking on premises

Gym

Serviced Apartment

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.