Monthly Rentals in Winter Harbor

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

Nearby monthly rentals

Top guest favourite
Guest house in Wolfeboro
4.98 out of 5 average rating, 198 reviews

A charming loft Barn that sleeps 5.

DanielRating, 5 stars1 week ago
This barn is absolutely beautiful and unique. The bar, furnishings, and wall art were all phenomenal. It was perfect for two couples to stay over a wedding weekend. We were able to freely enjoy ourselves and relax in a space that felt both special and homey. My one regret was that the weather didn’t allow us to use the fire pit in the yard. Communication was excellent, and Heidi was great to work with. Arriving there for the first time, I had one of those "I hope I should be driving down this private driveway!?" moments, but Google Maps took us exactly where we needed to be. I absolutely cannot wait to book here again. We will be back this fall without a doubt. Thank you, Heidi!
Guest favourite
Flat in Wolfeboro
4.86 out of 5 average rating, 59 reviews

Surrounded by Recreation (2)

TracyRating, 5 stars1 month ago
The place was great. It is right on a river and walking path and very close to town. The amenities were great. The place was clean, and Ruth was extremely responsive.
Superhost
Home in Wolfeboro
4.9 out of 5 average rating, 31 reviews

The Wolf Den in Wolfeboro, NH

RobynRating, 5 stars1 day ago
We stayed at Carolinas place for 4 days. Had tickets to a show in Gilford (30mins away) it’s adorable! It was perfect. It was clean, decorated so nicely and she had coffee, spices & condiments and a bag of ice! Even wood for the outdoor deck fireplace. Our dogs loved hanging out with us outside. Carolina told us about a few places to go for food & drinks. She responded quickly and was happy to answer my questions. The Boat house restaurant is great, big bar!and the Downtown is on the water. Great view and awesome food & service! Yum Yums has baked goods and ice cream. Lots of unique shops. Check out the Antique barn! The Alton beach had walking paths as well as the rail trail in town (that was a great walk!) We had a wonderful time and definitely will be back!!!
Guest favourite
Flat in Wolfeboro
4.89 out of 5 average rating, 19 reviews

Peaceful getaway with King Bed near Town

EmilyRating, 5 stars3 weeks ago
The place was very close to the center of town and everything in the apartment was well kept!

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 wifi 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.