Monthly Rentals in Bearsville, Woodstock

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

Nearby monthly rentals

Superhost
Cottage in Woodstock
4.91 out of 5 average rating, 176 reviews

Private Modern Cottage, Tranquil & Clean

NicoleRating, 5 stars7 months ago
This was a lovely location at an even lovelier home! I had a great stay in this quiet, peaceful modern cottage. Everything was spotless when I arrived and Sarah and Deandrea were always responsive and helpful. The place and its surroundings is full of beauty, from the giant windchime by the trees, the pink chairs on the green lawn frequently visited by the neighborhood deer, and the artwork and books in the apartment. Sitting outside was so serene, and there is a big table out front for meals or just working or sketching. The place is a short drive to the main street in Woodstock. Everything you need is just a short drive away: from beautiful hikes to live music and restaurants. I look forward to staying again sometime soon.
Top guest favorite
Guesthouse in Bearsville
4.98 out of 5 average rating, 612 reviews

Mt. Guardian Guest House Exquisite Mountain Views

WrenRating, 5 stars4 weeks ago
A haven of trees, even in the season when the trees are bare, provided breathtaking views from every angle, creating exactly the restorative environment we needed for a weekend away. The kitchen was well-stocked with everything needed to cook at home, but of course Woodstock just around the corner is in incredible town with so much to offer and explore! Everything was perfect. We hope to return.
Top guest favorite
Guesthouse in Bearsville
4.98 out of 5 average rating, 526 reviews

Relax on the Ridge - 2 miles from Woodstock

BrentRating, 5 stars4 days ago
it was a fantastic base to get dinner in Woodstock and see a show at the bearsville theater. The giant bed is so comfortable it's prompting me to replace my mattress at home.
Guest favorite
Bungalow in Bearsville
4.9 out of 5 average rating, 10 reviews

*New* Tranquil Designer Bungalow in the Woods

YoungwoongRating, 5 stars3 months ago
Meghan was a great host, our stay was truely enjoyable. The place was exceptionally well-maintained—everything was spotless, and it was clear that a lot of care goes into keeping it in top condition. The interior was beautifully designed, with a stylish and cozy atmosphere that made it feel like a home away from home. From the comfortable furnishings to the thoughtful decor, every detail was just right. I highly recommend this place to anyone looking for a clean, well-kept, and aesthetically pleasing stay. Would definitely book again!

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 Bearsville, Woodstock's top sights

Bearsville Theater195 locals recommend
The Bear Cafe167 locals recommend
Dixon Roadside65 locals recommend
Cub Market53 locals recommend
Nancy's Of Woodstock - Artisanal Creamery36 locals recommend
Commune Saloon21 locals recommend
*Some exclusions may apply in certain geographies and for some properties.
  1. Airbnb
  2. United States
  3. New York
  4. Ulster County
  5. Woodstock
  6. Bearsville
  7. Monthly Rentals