Available Listings

$12,000 / mo (USD)
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Rhinebeck Area Rental Property

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74 Hilltop Rhinebeck, NY 12572

3 Bed
4 Baths
3273 sqft
MLS# 20261450
Welcome to 1000 Oaks, a distinctive Rhinebeck country retreat. Set on 6.8 acres, this summer rental offers a 3,200+ square-foot main house and a heated 14' x 26' gunite pool, all surrounded by the quiet beauty of the Hudson Valley landscape. Like many exceptional homes shaped by a clear point of view, 1000 Oaks reflects the spirit of wabi-sabi, the time-honored Japanese philosophy that finds beauty in imperfection, simplicity, and harmony with the natural world. Here, the landscaping remains intentionally natural, wildflowers are welcomed and cultivated, and materials such as wood, fieldstone, and brick are thoughtfully woven throughout the property. Inside and out, a soft palette of earthy, low-contrast tones creates an atmosphere that is calm, grounded, and quietly beautiful. The home offers several especially appealing features. The family room includes an attached full bath, making it ideal for visiting guests. On the second floor of the tower, an office provides two dedicated workspaces, while the tower's third floor serves as a workout space, with walls of windows overlooking the property. In summer, once the trees are fully leafed out, the setting becomes especially secluded and serene. The heated pool is, of course, one of the season's great pleasures. Despite its sense of privacy and retreat, 1000 Oaks is conveniently located just 6 miles from the center of Rhinebeck Village, 6 miles from the Taconic State Parkway, and only a short distance from the Rhinebeck Performing Arts Center. Whether your summer in Rhinebeck or the Hudson Valley is devoted to rest, work, culture, or simply a change of rhythm, 1000 Oaks offers a setting with a strong sense of place. Its beauty is not formal or showy. It lies, instead, in the quiet coherence of the house, the land, and the life they make possible together. A 3D Walkthrough Tour is available in the digital Lookbook or by request.
Listing by: Hudson Valley Catskills MLS / Listed By: Feng Liu-Winham, Coldwell Banker Village Green Realty
$12,000 / mo (USD)
Active

Rhinebeck Area Rental Home

Active

74 Hilltop Road Rhinebeck, NY 12572

3 Bed
4 Baths
3273 sqft
MLS# 974131
Virtual Tour
Welcome to 1000 Oaks, a distinctive Rhinebeck country retreat.
Set on 6.8 acres, this summer rental offers a 3,200+ square-foot main house and a heated 14' x 26' gunite pool, all surrounded by the quiet beauty of the Hudson Valley landscape.
Like many exceptional homes shaped by a clear point of view, 1000 Oaks reflects the spirit of wabi-sabi, the time-honored Japanese philosophy that finds beauty in imperfection, simplicity, and harmony with the natural world. Here, the landscaping remains intentionally natural, wildflowers are welcomed and cultivated, and materials such as wood, fieldstone, and brick are thoughtfully woven throughout the property. Inside and out, a soft palette of earthy, low-contrast tones creates an atmosphere that is calm, grounded, and quietly beautiful.
The home offers several especially appealing features. The family room includes an attached full bath, making it ideal for visiting guests. On the second floor of the tower, an office provides two dedicated workspaces, while the tower’s third floor serves as a workout space, with walls of windows overlooking the property. In summer, once the trees are fully leafed out, the setting becomes especially secluded and serene. The heated pool is, of course, one of the season’s great pleasures.
Despite its sense of privacy and retreat, 1000 Oaks is conveniently located just 6 miles from the center of Rhinebeck Village, 6 miles from the Taconic State Parkway, and only a short distance from the Rhinebeck Performing Arts Center.
Whether your summer in Rhinebeck or the Hudson Valley is devoted to rest, work, culture, or simply a change of rhythm, 1000 Oaks offers a setting with a strong sense of place. Its beauty is not formal or showy. It lies, instead, in the quiet coherence of the house, the land, and the life they make possible together. A 3D Walkthrough Tour is available in the digital Lookbook or by request.
Listing by: ONEKEY as distributed by MLS GRID / Listed By: Feng Liu-Winham, Coldwell Banker Village Green Realty
$9,000 / mo (USD)
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Woodstock Area Rental Property

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3870 New York 212 Woodstock, NY 12498

3 Bed
2 Baths
1920 sqft
MLS# 20262019
Woodstock Summer 2026! Perched on a hill with panoramic views of the Cooper Lake this residence seamlessly blends European sophistication with Woodstock country vibes.

Designed with an emphasis on light and line, the home features an open-concept layout framed by floor-to-ceiling glass, ensuring the mountain and lake vistas remain the focal point of every room. The interior aesthetic is a refined nod to ''Old World'' quality met with modern minimalism. The main living space is an airy, voluminous great room featuring clean architectural lines and a seamless transition to the expansive outdoor terrace and gardens.

The exterior spaces are designed for effortless summer entertaining. Whether you are hosting a sunset dinner on the deck or enjoying a quiet morning overlooking the reservoir, the setting is one of absolute tranquility.

Located on one of the most coveted roads in the region, you are minutes away from the vibrant heart of Woodstock - renowned for its world-class dining, boutiques, and storied arts scene - while feeling worlds away in a private hilltop enclave.

Inquire today to secure your summer escape in the Catskills. Rent by the month or the full season. This is a Summer Monthly Rental Rate. For longer-term rental rates, please inquire.
Listing by: Hudson Valley Catskills MLS / Listed By: Melissa "Zoe" Hirsch, Coldwell Banker Village Green Realty
$7,000 / mo (USD)
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Windham Area Rental Property

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53 Windham Mountain Village Windham, NY 12496

2 Bed
2 Baths
1390 sqft
MLS# 20260983
Seasonal Rental | Windham Mountain Village | Windham Mountain Club

Enjoy next ski season in this beautifully renovated Windham Mountain Village townhouse, ideally located just steps to the slopes and lodge, with easy walk-to-lift access at the Windham Mountain Club. Thoughtfully updated in June 2025, this inviting residence lives as a 3-bedroom (legal 2-bedroom + flex room) and offers the perfect blend of comfort, convenience, and mountain lifestyle. The main level welcomes you with soaring vaulted ceilings, abundant natural light, and a cozy wood-burning fireplace, creating the perfect apres-ski setting. The updated kitchen features granite countertops, breakfast bar seating, and stainless-steel appliances, complemented by new flooring, solid 6-panel doors, fresh paint, and a brand-new split unit for efficient heating and cooling. Step outside to your newly built deck and porch overlooking the tennis courts, offering a peaceful setting for morning coffee or evening unwinding. Additional highlights include off-street parking and a flexible floor plan ideal for hosting. As part of Windham Mountain Village, tenants enjoy access to an exceptional clubhouse experience, featuring: Dining area with outdoor fire table and direct ski slope views. Fitness center, Game room, Indoor pool, & hot tub. Available for the 2026 season ( November 15,2026 to April 15th 2027), with flexibility on lease dates. Whether you're looking for a spring/summer/fall escape or an extended mountain retreat, this turnkey townhouse delivers comfort, amenities, and unbeatable proximity to everything Windham has to offer. Call/Text today to schedule a private showing or request a 3D walkthrough.
Listing by: Hudson Valley Catskills MLS / Listed By: Regina Tortorella, Coldwell Banker Village Green Realty
$3,950 / mo (USD)
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Olive Area Rental Property

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20 Mary Lou Shokan, NY 12481

4 Bed
2 Baths
1590 sqft
MLS# 20263714
This bright and beautifully updated raised ranch seamlessly blends classic charm with the modern appeal of a new build. Nestled in a serene neighborhood on a quiet cul-de-sac in the low-tax town of Olive, ideally situated between Woodstock and Phoenicia, this fully-renovated home offers the perfect combination of style, comfort, and convenience. At its heart is a stunning kitchen featuring a breakfast bar, American walnut countertops, an induction range with double oven, and premium LG and GE Café appliances throughout. The upper floor showcases solid oak flooring and a spacious primary bedroom with an en-suite bath complete with double sinks. Two additional bedrooms and an updated bathroom with a bathtub ensure comfort and style. Just off the living room, a covered porch invites you to entertain or relax with a quiet morning coffee, surrounded by the beauty of nature. The lower level offers ample space to create a home gym, playroom, or hobby area tailored to your lifestyle. A separate room provides the ideal setup for a home office, guest accommodations, or both. For added convenience, a front-loading LG washer/dryer combo completes the downstairs. The entire home (including the two-car garage) is climate-controlled with seven energy-efficient Mitsubishi mini splits, ensuring year-round comfort. The upgraded 200-amp service is generator-ready with an outdoor 30-amp service plug for peace of mind. A spacious outdoor shed provides ample storage for tools, equipment, or outdoor gear, while the short driveway and mostly wooded 0.5+ acre parcel add natural beauty and keep maintenance low.
Listing by: Hudson Valley Catskills MLS / Listed By: Benjamin Armento, Coldwell Banker Village Green Realty