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 reviews

The 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 reviews

Cottage 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 reviews

Farm 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 reviews

Suite 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.

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.

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