Monthly Rentals in Winchester

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

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Nearby monthly rentals

Superhost
Apartment in Putney
4.93 out of 5 average rating, 81 reviews

Southern Vermont Getaway

KristyRating, 5 stars4 months ago
Gay was very helpful and informative. Besides the dish soap, cleaning supplies, towels and linens, Gay had provided shampoo and conditioner. She even came up with a small grill for us to use during our stay. The Airbnb is part of a renovated barn which used to be Gay's mother's apartment. It was quite cute and comfortable! Thank you Gay for a very enjoyable stay!!
Guest favourite
Apartment in Vernon
4.96 out of 5 average rating, 156 reviews

Farm land view.

EvandroRating, 5 stars2 months ago
Peter is a great guy! I definitely recommend! Nice quiet little town!
Guest favourite
Cottage in Bernardston
4.88 out of 5 average rating, 314 reviews

Cozy, Quiet Cottage on Country rd 2 mil from I-91

NorrieRating, 5 stars1 month ago
This is my second Christmas staying at Chris’s place. I really enjoy this cozy cottage. I spend time with my family, Bella plays with their dogs, and then we have our own special place to go home too. Bella really enjoys the outside, I very much enjoy the inside! Thank you so much for taking good care of us. See you next year. 🤞
Superhost
Chalet in Winchester
4.84 out of 5 average rating, 110 reviews

Chalet Sonsie: A Sweetwater Stay

CaseyRating, 5 stars1 week ago
The house was clean and beautiful. The fireplace was a romantic and cozy element for the cold weather of February. We love to cook and were very happy with the nice gas stove. I would definitely rent this location again.

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.