Woodstock, NY Homes for Rent

A stunning, fully furnished guest house in a private setting in Woodstock! There's nothing more to ask for in this single level guest home with two bedrooms, a single bathroom and stunning open kitchen and living area. This home is naturally well-lit including skylights and picturesque nature views from each window. If this wasn't enough inside, step outside to your private outdoor area with

Amy Hawks Berardi Realty

Sweet bungalow in Bearsville available for rent and move in ready. Down private country lane situated next to lovely stream on almost 3 acres minutes to the center of Woodstock sits this remodeled 2 Bd/ 1 Ba home with polished concrete floors and perfectly furnished with a modern aesthetic. Sit on your covered deck looking out into the Catskill forest. Lounge in your cozy living room beside your

Johanna Trimboli Halter Associates Realty

*SUMMER RENTAL* (AVAIL May 25 - Sep 7, 2026) // This unique hilltop property includes two separate structures -- a beautifully designed three-bedroom main house and a private loft guest house offering flexible space so you have accommodations for up to 10+ guests. Tucked away on a private hilltop ridge just under three miles from the pulse of Woodstock, 55 Nordic Drive is a secluded Catskills

Alexis Li Corcoran Country Living

Beautifully renovated 1-bedroom, 1-bath home in the heart of Woodstock, just 90 miles from NYC. Ideally located in downtown Woodstock, walking distance to restaurants, bars, shops, markets, bakeries, pharmacies, galleries, cinema, and theater. Originally an 1890s farmhouse, this unit has been thoughtfully reimagined with a bright, open-concept layout featuring expansive windows, a spacious living

James Angelakis BHHS HUDSON VALLEY PROP-WDST

A truly one-of-a-kind residence and rare opportunity, this exceptional home offers a seamless blend of architecture and art in the heart of Woodstock, walking distance to Tinker Street, yet set privately on 1.73 secluded acres just minutes from the village.Designed as a fusion of a Frank Lloyd Wright–inspired contemporary addition and an original Buckminster Fuller–style geodesic dome, the

Ashley Olson Minard eXp Realty

With its very close proximity to Woodstock village, this is the perfect location if you're looking to engage in the vibrant artistic community yet yearn for woodsy privacy! This elegant yet simple home is very cozy with a modern kitchen, wood floors throughout, a family room in addition to the living room. and an office space. Three bedrooms are upstairs: a very large primary bedroom with 1/2

Sylvie Ross Halter Associates Realty

Situated on nearly an acre of manicured green grass, fruit trees, and mountainous woods in the heart of the Woodstock NY in the Catskills, this roughly 3,000 square foot 5-bedroom, 3-bathroom home is the perfect balance between peaceful nature and the higher-end comforts of being near the city. The house has a big master bedroom with large windows facing nature and easily fits a king size bed.

Jerry Weiss Pietro Altomare Realty

Luxury 3-Bed, 2-Bath Spa Retreat on over 6 Acres - Jet Tub, Sauna, Fire Pit & Handcrafted Natural Design Just 10 minutes from the heart of Woodstock and 5 minutes from the Bearsville Theater and restaurants, this stunning 3-bedroom, 2-bath retreat combines luxury, craftsmanship, and nature in perfect harmony. Every detail has been thoughtfully designed using only natural materials - stone, wood,

Susanna Scott-Mitchell Compass Greater NY, LLC

2 bedroom farmhouse on beautiful John Joy Road available October 1st through May 31st for 6 months or more. Set toward the back of a 3 acre meadow far from the road and bordering a beautiful forest, this charming home is just a mile or so from Woodstock Day School and 3 miles to the Zena Democratic School. Relax on the deck and take in the change of seasons and wildlife that meanders through the

Sean Zimmerman Halter Associates Realty

Beautifully renovated farmhouse set on 4.65 private acres with seasonal mountain views. This fully furnished 3BR/2BA home features an open floor plan, custom kitchen with vaulted ceilings, high-end appliances, marble countertops, and hardwood floors throughout. Living room with cobblestone fireplace and French doors to covered porch. Screened porch and large back deck overlook lush grounds.

Susanna Scott-Mitchell Compass Greater NY, LLC

ANNUAL FURNISHED RENTAL w POOL Lovely, meticulously maintained 3 bd/2 ba home with flex room and finished basement on amazing road. 3 plus bucolic acres minutes to the center of Woodstock HW floors, gourmet kitchen, living room with beautiful stone fireplace. Stone patio perfect for eating al fresco Sprawling grounds and gardens. Plenty of room to enjoy hosting family and friends.

Johanna Trimboli Halter Associates Realty

SHORT TERM RENTAL: Private, fully furnished Woodstock Oasis with mountain views, is ready to be your country getaway! On a dead-end rd. up high on a hill, this Willow home has everything you need, close to hiking, skiing, restaurants and shopping, just minutes from Woodstock, Phoenicia and the NYS Thruway, this private retreat is available beginning March 2026

Mark Kanter BHHS HUDSON VALLEY PROP-WDST

AVAIL FROM SEPT 2025. Private & Serene Modern Farmhouse Near Woodstock - Nestled on a private road just minutes from the heart of Woodstock, this beautifully renovated 4-bedroom, 2.5-bathroom modern farmhouse offers the perfect blend of charm, space, and privacy. Surrounded by mature trees, stone walls, and tall hedges, this home feels like a secluded retreat while remaining conveniently close to

Alexis Li Corcoran Country Living

AVAIL FROM SEPT 2025. Secluded Mountain Chalet with Breathtaking Views and Poolside Lodge - Set atop nine private acres, this stunning mountaintop chalet offers a rare combination of serenity, seclusion, and spectacular views. A long, private driveway winds through the property, leading to a retreat unlike any other. The property features a three-story main house and a separate two-story Poolside

Alexis Li Corcoran Country Living