Monthly Rentals in Windsor

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

Nearby monthly rentals

Top guest favorite
Home in West Windsor
4.97 out of 5 average rating, 117 reviews

Birdie's Nest Guesthouse

DianaRating, 5 stars5 days ago
We loved our two nights here. Idyllic setting, easy driving to gorgeous Woodstock. The house is exactly as described with an easy to use kitchen, gorgeous bathroom and comfy bed! We can’t wait to come back to visit in the fall.
Top guest favorite
Home in West Windsor
4.98 out of 5 average rating, 198 reviews

Meadow View. 35 acres outside your door!

SofiaRating, 5 stars2 months ago
Daniel and Sondra were great! Very responsive, super helpful, and they gave great recommendations on things to do and restaurants. The location was nice, private, but not too far from nearby towns. Definitely recommend!
Top guest favorite
Cottage in Windsor
4.97 out of 5 average rating, 379 reviews

Ogden's Mill Farm

KelseyRating, 5 stars2 weeks ago
We absolutely loved our stay here!! It was easily the best AirBnB I've ever stayed in. The whole property was stunning and we were able to hike and walk around the whole thing!! There is an adorable dog and horses as well that made us feel right at home. The area is private and clean with an amazing kitchen to cook in! We also loved how there was a binder of recommendations for hikes, food, activities etc. as we are not from the area. I would recommend this location to every one of my friends and family and we ABSOLUTELY plan on staying here again; worth every single penny!
Guest favorite
Home in West Windsor
4.93 out of 5 average rating, 43 reviews

Chuck's Place

LeslieRating, 5 stars1 month ago
We rented Chuck’s Place for 8 weeks to use as a ski house for this winter. This house is located 35 minutes from Okemo, 45 minutes from Sunapee and 25 minutes from the Woodstock Nordic Center. It has everything you need including a well-stocked kitchen and two bathrooms. It is actually nicer than the pictures show as they have done some renovations. We especially enjoyed relaxing in the living room after a long day of skiing and watching the sun set on Mount Ascutney. Access to a garage was a major plus for the winter! We also loved being able to use the gas grill the whole time. Ed and Jennifer live nearby and responded promptly if any issues arose. We can’t say enough great things about this place. We felt right at home and are going to miss that view!

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

Traveling 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 Windsor's top sights

Harpoon Brewery Taproom and Beer Garden125 locals recommend
Saint-Gaudens National Historical Park62 locals recommend
Windsor Station Restaurant & Barroom33 locals recommend
Brownsville Butcher & Pantry32 locals recommend
Cornish-Windsor Covered Bridge28 locals recommend
Price Chopper27 locals recommend
*Some exclusions may apply in certain geographies and for some properties.
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