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, 108 reviews

The Overlook: A Sweetwater Stay

ChrisRating, 5 stars2 weeks ago
Second time staying at one of Pattis stays. The fisheing cabin on Tully lake was larger and rustic and perfect for the guys trip that we did 3 years ago. The Winchester was idealic , tastefully blending modern with a rustic touch and ideal for my fiance and our own trip. both times our dog enjoyed the trip and nature-will surely stay at one of Patti's listings again. This is a responsible , responsive and tastefull Airbnb host. Anyone looking for a quiet retreat would find what they need. thank you for the recharge patti.
Top guest favourite
Guesthouse in Dummerston
5 out of 5 average rating, 10 reviews

Cottage amongst the trees

AldenRating, 5 stars5 days ago
Aisha and John were a phenomenal hosts and their communication was amazing . I ended up staying in the amazing place for 3 weeks. I have zero complaints. Very cozy, has all the essentials in a perfect little package, amazing heat/air conditioner, and amazing bed. Also the free Coffee provided was a huge plus. I will be looking to re booking with them.
Guest favourite
Apartment in Town of Rockingham
4.91 out of 5 average rating, 77 reviews

Lovely light-filled 2 bedroom flat

PremRating, 5 stars8 months ago
We really enjoyed our stay at Kristen’s place in Rockingham. Location was perfect, very quiet at night and very easy to walk into the little town of Bellows Falls. The bed was comfortable and the apartment was very spacious. We would highly recommend and definitely return.
Guest favourite
Tiny homes in Brattleboro
4.94 out of 5 average rating, 161 reviews

“Hickory” Rustic Cabin Retreat with Fireplace

NatalieRating, 5 stars3 weeks ago
Had a solo trip the cabin was super clean it is dog friendly and I was surprised that there wasnt even any dog hair on the furniture. Host was on property and super nice. Place was very quiet and peaceful. Local restaurants and shops were nice. It does rain a lot and can get pretty muddy but i just took my shoes off when i went inside. Hot tub is clean and plenty of bathroom options.

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.