Monthly Rentals in Winchendon

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

Nearby monthly rentals

Top Guest favourite
Guest suite in Ashburnham
4.98 out of 5 average rating, 466 reviews

The Ginger Bed King Suite

SallyRating, 5 stars1 week ago
It was a pleasure staying at Laura and Michael's lovely and comfy king guest suite, with its historic details and eclectic furnishings. The kitchen area had everything needed to start the day including breakfast. The large bathroom was spotless and up to date. I was surprised at the spaciousness of the bedroom and wish I had the bed in my own home. The only downside was rain, which prevented me from sitting outside and enjoying charming garden.
Top Guest favourite
Guest suite in Hubbardston
4.99 out of 5 average rating, 123 reviews

In-law Apartment, Full Kitchen, Near Mt Wachusetts

JessicaRating, 5 stars3 days ago
Melinda was super responsive to a couple questions I had. Was able to suggest some local restaurants to eat at. Instructions were clear and check in/out was super easy. Super clean, quiet and looks exactly like photos.
Top Guest favourite
Guesthouse in New Ipswich
4.95 out of 5 average rating, 358 reviews

"The Porch" Your cozy home away from home!

BrianaRating, 5 stars5 days ago
I was traveling alone to visit friends in the area and The Porch was the perfect space for me! It was beautiful and I felt safe in the area. Everything I didn’t even know I needed was available. Driving in the area was a little tricky at night, as someone who hasn’t navigated NH much, but John’s detailed directions and descriptions helped when I arrived in the dark. I would absolutely stay here again!
Top Guest favourite
Place to stay in Winchendon
4.92 out of 5 average rating, 72 reviews

Enjoy your stay in an Antique Home in a Toy Museum

LovelyRating, 5 stars2 weeks ago
We (children and adult) loved Don's home. The decorations will take you back to your grand-parents years, clean, lots to do indoor, so many ways to get upstairs. The water pressure was very therapeutic for many of us. The beds were "Ahhh, fresh air" after a long day. Extra blankets were available. This home was very different (museum) which made it super interesting for the children. Coffee/tea and snacks were available. Very spacious, safe, and enabled great views. I recommend this home for business or family gathering. Thanks for being very responsive, Don.

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 holiday 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 Wi-Fi and dedicated working spaces.

Looking for corporate housing?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing and relocation needs.
*Some exclusions may apply in certain geographies and for some properties.