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Monthly Rentals in Winchester

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

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Nearby monthly rentals

Guest favorite

Rental unit in Winchester

4.91 out of 5 average rating, 191 reviews

Downtown Loft next to Distillery

Guest favorite

Rental unit in Vernon

4.96 out of 5 average rating, 153 reviews

Farm land view.

Guest favorite

Cottage in Bernardston

4.88 out of 5 average rating, 307 reviews

Cozy, Quiet Cottage on Country rd 2 mil from I-91

Superhost

Rental unit in Brattleboro

4.8 out of 5 average rating, 91 reviews

Artsy Studio w/Fireplace - Pet-Friendly!

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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 & traveling professionals

Comfortable accommodations for nomadic and remote working professionals with wifi and dedicated work spaces.

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 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

Kitchen
Wifi
Pet friendly
Laptop-friendly workspace
Free parking on premises
Corporate Housing

Stay near Winchester's top sights

Pisgah State Park21 locals recommend
Northfield Drive-In Theatre13 locals recommend
New England Sweetwater Farm & Distillery10 locals recommend
The Rustic Table8 locals recommend
Kulick's Market7 locals recommend
Kilburn Pond Trailhead Pisgah State Park6 locals recommend

Destinations to explore

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