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
4.88 out of 5 average rating, 104 reviews

The Overlook: A Sweetwater Stay

LeeRating, 5 stars1 month ago
Great overall experience, I would recommend.
Guest favourite
Apartment in Winchester
4.91 out of 5 average rating, 195 reviews

Downtown Loft next to Distillery

VidaRating, 5 stars3 weeks ago
This cozy downtown spot was perfect for a relaxing getaway. We stayed during my post-surgery recovery, and the HD entertainment system made for the ultimate movie marathon. The wall of windows filled the space with beautiful natural light, making even the chilly winter days feel warm, especially with a cup of tea in hand. Naomi was incredibly accommodating and responsive, ensuring we had everything we needed. The area has great walkable paths for our dog, plus Keene’s restaurants and a grocery store are just a short drive away. The hourly bells were hardly noticeable and never disruptive. Would absolutely stay again! 10/10 recommend!
Apartment in Winchester
4.67 out of 5 average rating, 43 reviews

Beautiful lake side getaway, quiet.

MilsRating, 5 stars7 months ago
This is a really beautiful and peaceful location! After a rocky start we had a wonderful time and made a lot of memories. Fishing was great and we loved taking the kayaks out on the lake. Definitely a place to visit again.
Guest favourite
Apartment in Keene
4.98 out of 5 average rating, 41 reviews

Cozy Downtown Keene Private Apartment

DianaRating, 5 stars3 months ago
My daughter and her husband thoroughly enjoyed their stay, were very cozy & comfortable! The space & location were perfect for their Christmas visit with family near by in Keene & Jaffrey. Thank you Chris!

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.