Monthly Rentals in Chappaqua

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

Nearby monthly rentals

Top guest favourite
Apartment in Ossining
4.96 out of 5 average rating, 432 reviews

Hudson River Peaceful Getaway, Explore from here

BrianRating, 5 starstoday
This was the best stocked Airbnb that I have ever stayed at. If you forgot to bring something, not to worry it was here. The view of the Hudson river in that region is unmatched. You will not find any more scenic. Clean, modern open floor plan that lets in plenty of light to allow the full experience of the extraordinary view. It is not far from the historic and notorious Sing Sing correctional facility. I wish I could have stayed longer.
Top guest favourite
Guest suite in Pleasantville
4.84 out of 5 average rating, 69 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!
Guest favourite
Apartment in Mount Kisco
4.9 out of 5 average rating, 79 reviews

Clean,Comfy & Convenient. Private 1Bed Village Apt

JasonRating, 5 stars1 week ago
This is a great place in the village of Mt. Kisco. Walkable to great restaurants and shops. Matt was fabulous. Always available when needed. I highly recommend it!
Top guest favourite
Barn in Mount Kisco
4.91 out of 5 average rating, 576 reviews

NY Rustic Cottage Getaway

DanielRating, 5 stars3 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.

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 Chappaqua's top sights

Jacob Burns Film Center33 locals recommend
Village Social Kitchen & Bar17 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
*Some exclusions may apply in certain geographies and for some properties.