
Monthly Rentals in Winchester
Discover long-term rentals that feel like home for stays of a month or longer.
Nearby monthly rentals
Guest favourite

Tiny homes in Winchester
4.87 out of 5 average rating, 107 reviewsThe Overlook: A Sweetwater Stay
DeniseRating, 5 stars2 weeks ago
Patti’s Airbnb was absolutely beautiful! A perfect place to stay to get away from the hustle and bustle! Every nook in the house was thoughtfully made for a relaxing retreat! Look forward to renting again !
Top guest favourite

Guesthouse in Dummerston
5 out of 5 average rating, 9 reviewsCottage amongst the trees
BrianRating, 5 stars1 month ago
It’s not the size of the dog in the fight…these guys spared no expense when refurbishing this amazing lil gem. I’d literally live there and not even flinch. I’m actually staying somewhere else right now (basic motel room) and it seems too big! Was thinking they could get away with fun colors/darker wall paint. Anyway, from the cabinets to the shower to the vibrating bed (after ski ecstasy) which also moves in every position possible…being single, it was the one night I didn’t feel lonely while sleeping. Haha. 👍👍 Good people, positive vibes. Prayers I can get back. 🙏
Top guest favourite

Apartment in Vernon
4.96 out of 5 average rating, 160 reviewsFarm land view.
LorrieRating, 5 stars1 week ago
Our return trip was just as great as the first time there. The apartment was spotless, the furniture and bedding is very comfortable. Has everything we needed. It is in a beautiful location 10 minutes from Massachusetts and New Hampshire. We feel at home and very safe . Peter is a great host and communicates very quickly. Looking forward to another visit.
Guest favourite

Guest suite in Winchester
4.97 out of 5 average rating, 143 reviewsSuite 1 - Stay at a craft brewery - Winchester NH
GraceRating, 5 stars6 months ago
We had a wonderful time at this place! The property is beautiful, easy to find and parking was convenient. They are incredibly dog friendly and our pup loved the yard & brewery nearby on the same property! We had a wedding in Brattleboro VT, which was easily driveable from the air BNB.
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
Travelling 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.