$18,592 per month
28 Holiday Dr Unit ID1300133P, Woodstock, NY 12498
The advertised rate of $18,592/month is the lowest available price, based on a 30 day(s) stay with a move-in date of May 30, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$6,500 per month
106 Mountain Laurel Ln, Woodstock, NY 12498
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
$7,442 per month
21 Abbey Rd Unit ID1241292P, Mount Tremper, NY 12457
The advertised rate of $7,443/month is the lowest available price, based on a 1 month(s) stay with a move-in date of April 6, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$16,000 per month
70 Raybrook Dr, Woodstock, NY 12498
Welcome to a home where contemporary elegance seamlessly blends with the tranquil beauty of nature. Nestled among lush greenery and towering pines, this stunning residence, worthy of features in top architectural publications, offers an unmatched living experience. At the end of a quiet, winding drive, this property reveals breathtaking views of a dramatic wooded hillside cascading down to a
Melissa Zoe Hirsch Coldwell Banker Village Green
$4,000 per month
180 Yerry Hill Rd, Woodstock, NY 12498
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
$4,700 per month
41 Park Dr, Woodstock, NY 12498
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
$5,500 per month
299 Wittenberg Rd, Bearsville, NY 12409
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
$5,500 per month
10 Purdy Hollow Rd, Woodstock, NY 12498
Fully Furnished Winter Seasonal Rental Opportunity Embrace winter in the Catskills in this fully furnished, beautifully renovated cedar contemporary home, ideally located in the peaceful hamlet of Zena, just five minutes from the vibrant town of Woodstock. Situated on three private acres and directly across from the 60-acre Thorn Preserve, this sanctuary offers breathtaking views of the Catskill
Sarah Stoudt Coldwell Banker Village Green
$2,600 per month
259 John Joy Rd, Woodstock, NY 12498
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
$4,900 per month
17 Cross Patch Rd, Willow, NY 12495
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
$5,300 per month
33 Race Track Rd, Bearsville, NY 12409
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
$4,000 per month
295 Grog Kill Rd, Willow, NY 12495
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
$6,500 per month
11 Shultis Farm Rd, Bearsville, NY 12409
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
Alexis Li Corcoran Country Living
$16,500 per month
75 Hill 99, Woodstock, NY 12498
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
When people think of Woodstock, the iconic 1969 festival comes to mind, even though it was held about 60 miles away in Bethel, New York. Today, this small mountain town still attracts tourists wearing tie-dye T-shirts and flowy skirts, but Woodstock ...
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