Monthly Rentals in Olive

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

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Nearby monthly rentals

Guest favourite

Guesthouse in Accord

4.94 out of 5 average rating, 140 reviews

Studio in Private Forest; Peace and Solitude

JarretRating, 5 stars1 month ago
Absolutely fantastic stay! The location is stunning, surrounded by breathtaking mountain views, and the peaceful atmosphere made it the perfect getaway. The host was incredibly welcoming, attentive, and made sure everything was just right. Highly recommend for anyone looking to relax and recharge in nature!
Guest favourite

Cottage in Woodstock

4.94 out of 5 average rating, 309 reviews

Cozy Woodstock cottage

CatRating, 5 stars6 months ago
As an experienced Airbnb guest, Janine’s place stands out for the special touches that make a place a home from home. Having great WiFi, tasteful furnishings and comfy beds are all wonderful, but going the extra yard to provide oil and vinegar, spices, storage containers, a water filter jug, ice trays, a moka express, cafetière and drip coffee maker (instead of environmentally horrific Keurig disposables) make a GREAT airbnb! All items that one would not travel with and are annoying to have to buy/bring yourself. One note for music lovers, bring a decent compact Bluetooth speaker and it will cover all the rooms easily. I enjoyed a 30-day July stay and marveled at the quiet and the light-filled space. Surrounded by trees but a 5 minute drive to Woodstock, it was as close to activity or as solitary as you choose. You get a cozy cottage that is the epitome of Catskills chic, and on some days you can see the colors of sunset through the trees. I cannot wait to return!
Guest favourite

Home in Olivebridge

4.93 out of 5 average rating, 240 reviews

Modern rustic catskill retreat

RachelRating, 5 stars1 month ago
Alessandro is a wonderful host, very responsive and helpful. We enjoyed our time at his place.
Guest favourite

Place to stay in Kerhonkson

4.95 out of 5 average rating, 19 reviews

Private Hudson Valley Studio

JaimeRating, 5 starstoday
perfect location and wonderful hosts! we love the space. very small for a family of three but definitely doable and everything was beautiful! would love to return!

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 Olive's top sights

Ashokan Reservoir232 locals recommend
Bread Alone Bakery156 locals recommend
Boiceville Supermarket117 locals recommend
The Country Inn68 locals recommend
Kenneth L. Wilson Campground57 locals recommend
Ashokan Rail Trail- Boiceville Bridge Trailhead52 locals recommend

Destinations to explore

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