Monthly Rentals in Pleasantville

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

Nearby monthly rentals

Top guest favorite
Guest suite in Pleasantville
4.84 out of 5 average rating, 68 reviews

Charming Studio Centrally Located in Pleasantville

GeraldRating, 5 stars1 month ago
Alison’s home was absolutely perfect for when I was visiting my boys who go to Pace University. It is within walking distance to Pace, the Metro North train station, the town, restaurants and supermarket. The neighborhood is very safe and peaceful. It was a pleasure to meet Alison who was super friendly. She went over everything that I needed to know about the apartment and area when I arrived. The kitchen was stocked with everything that I needed to make all of my meals and the bed was super comfy. The entire place was impeccably clean and had more than enough closet and drawer space to put away all of my belongings. Loved the private entrance and onsite parking. I will reserve this Airbnb again on my next visit. Thank you for a great stay!
Top guest favorite
Barn in Mount Kisco
4.91 out of 5 average rating, 575 reviews

NY Rustic Cottage Getaway

DanielRating, 5 stars2 weeks ago
One of the best Airbnb stays I’ve had. A restored barn-turned-guesthouse that’s peaceful, cozy, and tucked into nature, with thoughtful, artistic touches and its own little kitchen. As someone local to the area, I can say the location is perfect—quiet and calming, but close to Mt. Kisco’s best spots (coffee, bookstores, restaurants, a charming movie theater), plus great hikes and the train into the city. The bathroom was super clean and stocked with natural products, and the whole space feels intentionally designed—from furniture placement to the trees outside. You’ll wake up to birdsong, maybe spot a deer or two, and feel like you’re part of the landscape. Nina is a warm, grounded host who clearly cares about the experience—and she's refreshingly fair about the cleaning fee. A rare stay that feels both creatively inspiring and deeply restful. Would absolutely come back.
Superhost
Home in Chappaqua
4.87 out of 5 average rating, 77 reviews

Chic and Cozy 2BD 1920's Cottage Retreat

ChristyRating, 5 stars7 months ago
Elizabeth was amazing she was even helpful in suggesting some of the most extraordinary summer camp for our boy who loves sports! It was a very special month for us and an amazing break from Manhattan. The commute was so easy on metro north I walked to the train in the morning the days I had to go into work and it was so easy! Elizabeth is just the best
Guest favorite
Guesthouse in Chappaqua
4.86 out of 5 average rating, 29 reviews

Comfortable, clean studio guesthouse in Chappaqua

KaediRating, 5 stars5 months ago
Wonderful, bright, extremely clean space! Jennifer goes above and beyond to make you feel at home and provide all of the necessary amenities. Beautiful location! Thank you Jennifer for making everything so smooth and wonderful during my 1+ month stay!

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 Pleasantville's top sights

Jacob Burns Film Center33 locals recommend
Jacob Burns Media Arts Lab11 locals recommend
Starbucks10 locals recommend
Jean-Jacques' Culinary Creations10 locals recommend
The Black Cow Coffee Company9 locals recommend
Wood & Fire7 locals recommend
*Some exclusions may apply in certain geographies and for some properties.