Monthly Rentals in Lewisboro

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

Nearby monthly rentals

Superhost
Cottage in Pound Ridge
4.82 out of 5 average rating, 61 reviews

Pound Ridge Paradise: Your Private Cottage Retreat

SimiRating, 5 stars4 weeks ago
we love Walkers place and do come here twice a year. it's a beautiful home, it's so zen, so pretty, so clean, we just absolutely love it. it's a great fabulous house and spot to stay. ♥️
Guest favorite
Apartment in South Salem
4.77 out of 5 average rating, 48 reviews

Cozy Apartment in Horse Country

JenRating, 5 stars4 months ago
Unit was very clean, comfortable and just as described, and Tommy and his wife were very friendly and responsive!
Top guest favorite
Home in Bedford
5 out of 5 average rating, 26 reviews

The Waterside Home - Pool, Tennis, Sauna & Golf

CateRating, 5 stars4 months ago
We were fortunate to spend several months at the Waterside Home with our two children and our dog during our house renovation and couldn’t have asked for a more charming and peaceful spot. Jonathan is a wonderful host and was always responsive. Pictures cannot begin to do justice to the spectacular landscaping, the mature trees and paths carved through cultivated wildflower meadows. We loved playing tennis and pickleball with our kids. While given privacy, we all appreciated the well-cherished grounds. Inside, there was plenty of room to accommodate our family. It’s well-furnished, charming and functional and very much like a home rather than a rental house. The kitchen has everthing we needed. The primary suite in particular is lovely and large with stunning views over the reservoir. Last, the location is perfect within a few easy minutes of Katonah’s cute shops and restaurants and near 684 yet completely quiet, secure and tranquil. Thank you Jonathan for a perfect stay!
Guest favorite
Cabin in Pound Ridge
4.91 out of 5 average rating, 11 reviews

The Cottage on Maple Grove Farm

HaiqingRating, 5 stars4 months ago
We had a wonderful stay at this charming cottage. We experienced the first snow here, it was absolutely peaceful and serene. The cottage is located on a spacious farm, offering a perfect blend of privacy and convenience, with restaurants, grocery stores, and the train station all nearby. Communication with George was excellent—he checked in to ensure we had everything we needed, which made our stay even more enjoyable. Highly recommend this place!

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 Lewisboro's top sights

Ward Pound Ridge Reservation58 locals recommend
The Inn at Pound Ridge47 locals recommend
Ridgefield Playhouse32 locals recommend
Katonah Museum of Art32 locals recommend
Grace Farms31 locals recommend
The Aldrich Contemporary Art Museum29 locals recommend

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.