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$16,500 / mo (USD)
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Woodstock Area Rental Property

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75 Hill 99 Woodstock, NY 12498

4 Bed
3 Baths
2394 sqft
MLS# 20250507
AVAIL FROM OCT 2026. 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 Lodge, both connected by an expansive deck with a heated pool, open from mid-May through November 1st, and a built-in outdoor grill station perfect for entertaining.
Inside the main house, soaring cathedral ceilings and wide-plank wooden floors create an immediate sense of warmth and grandeur. The second floor spacious living room is anchored by a striking double-sided wood-burning fireplace, which also serves a cozy alcove office lined with picture windows--a peaceful and inspiring workspace. The adjoining kitchen is fully equipped with modern appliances, including an induction stovetop, oven, and two refrigerators. A large island with seating for four offers a casual spot for dining, while the adjacent alcove provides a more formal space with a handcrafted wooden table positioned to capture stunning views of the Hudson Valley. Step onto the wooden terrace for a peaceful morning coffee, watching the sunrise over the mountains. On clear days, the view stretches as far as the Berkshires. Behind the living room, two serene bedrooms, each with a queen-size bed, offer restful retreats. One overlooks the pool and deck area, while the other gazes out at the garden and bocce court. A beautifully designed modern bathroom sits just across the hall. A spiral staircase leads to the top floor, where the expansive primary suite is a sanctuary unto itself. Cathedral ceilings create an airy feel, while the en-suite bathroom is a luxurious escape, featuring a bubble-stream tub and a sunlit glass block windowed shower brings the outdoors in. A grand staircase leads to the first-floor great room, where another working fireplace, plush leather seating, and a cozy library plus corner bench seating reading nook create an inviting atmosphere. Behind the living area, a ground-floor bedroom offers a private retreat with french doors opening to nature and a handcrafted solid cherry Le Grange bed. An elegant en-suite Porcelanosa bathroom enhances this space, making it feel like a mini-suite. Stepping outside and crossing the pool deck brings you to the Poolside Lodge, an inviting space designed for relaxation and entertaining. The upper level is dominated by a grand room with walls of windows and private terrace that capture sweeping 180-degree mountian views. Luxurious leather seating and an open, airy layout make it the perfect place to gather. On warm days, four large french doors open to let in the fresh mountain air, creating an effortless indoor-outdoor flow. Downstairs, the lower level of the Poolside Lodge offers a spacious retreat with a piano, pool table, and gym equipment, providing plenty of space for recreation and entertainment. Beyond the homes, the lower portion of the property features a tranquil pond, ideal for rowing a boat or enjoying a picnic at the shaded table by the dock. The front of the main house opens to a vast, open lawn surrounded by wooded land, with a fire pit that invites guests to gather under the star-filled sky. For those who love the outdoors, the chalet is perfectly situated. Hunter and Belleayre ski resorts are just a 30-40 minute drive away, while nearby hiking trails offer endless opportunities to explore nature. Despite its secluded feel, the property is only two hours from New York City, making it an accessible escape from the hustle and bustle. This remarkable retreat is available for rent on a month-to-month or long-term basis starting September 1, 2025. This is more than just a rental--it's an experience.
Listing by: Hudson Valley Catskills MLS / Listed By: Alexis Li, Corcoran Country Living
$16,500 / mo (USD)
Active

Woodstock Area Rental Home

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75 Hill 99 Woodstock, NY 12498

4 Bed
4 Baths
4044 sqft
MLS# 831283
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 Lodge, both connected by an expansive deck with a heated pool, open from mid-May through November 1st, and a built-in outdoor grill station perfect for entertaining.
Inside the main house, soaring cathedral ceilings and wide-plank wooden floors create an immediate sense of warmth and grandeur. The second floor spacious living room is anchored by a striking double-sided wood-burning fireplace, which also serves a cozy alcove office lined with picture windows—a peaceful and inspiring workspace. The adjoining kitchen is fully equipped with modern appliances, including an induction stovetop, oven, and two refrigerators. A large island with seating for four offers a casual spot for dining, while the adjacent alcove provides a more formal space with a handcrafted wooden table positioned to capture stunning views of the Hudson Valley. Step onto the wooden terrace for a peaceful morning coffee, watching the sunrise over the mountains. On clear days, the view stretches as far as the Berkshires. Behind the living room, two serene bedrooms, each with a queen-size bed, offer restful retreats. One overlooks the pool and deck area, while the other gazes out at the garden and bocce court. A beautifully designed modern bathroom sits just across the hall. A spiral staircase leads to the top floor, where the expansive primary suite is a sanctuary unto itself. Cathedral ceilings create an airy feel, while the en-suite bathroom is a luxurious escape, featuring a bubble-stream tub and a sunlit glass block windowed shower brings the outdoors in. A grand staircase leads to the first-floor great room, where another working fireplace, plush leather seating, and a cozy library plus corner bench seating reading nook create an inviting atmosphere. Behind the living area, a ground-floor bedroom offers a private retreat with french doors opening to nature and a handcrafted solid cherry Le Grange bed. An elegant en-suite Porcelanosa bathroom enhances this space, making it feel like a mini-suite. Stepping outside and crossing the pool deck brings you to the Poolside Lodge, an inviting space designed for relaxation and entertaining. The upper level is dominated by a grand room with walls of windows and private terrace that capture sweeping 180-degree mountian views. Luxurious leather seating and an open, airy layout make it the perfect place to gather. On warm days, four large french doors open to let in the fresh mountain air, creating an effortless indoor-outdoor flow. Downstairs, the lower level of the Poolside Lodge offers a spacious retreat with a piano, pool table, and gym equipment, providing plenty of space for recreation and entertainment. Beyond the homes, the lower portion of the property features a tranquil pond, ideal for rowing a boat or enjoying a picnic at the shaded table by the dock. The front of the main house opens to a vast, open lawn surrounded by wooded land, with a fire pit that invites guests to gather under the star-filled sky. For those who love the outdoors, the chalet is perfectly situated. Hunter and Belleayre ski resorts are just a 30-40 minute drive away, while nearby hiking trails offer endless opportunities to explore nature. Despite its secluded feel, the property is only two hours from New York City, making it an accessible escape from the hustle and bustle. This remarkable retreat is available for rent for high season rates (inquire) July 7 - August 1, then on a month-to-month or long-term basis starting September 3, 2025. This is more than just a rental—it's an experience.
Listing by: ONEKEY as distributed by MLS GRID / Listed By: Alexis Li, Corcoran Country Living
$11,000 / mo (USD)
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Cold Spring Area Rental Home

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240 Lane Gate Road Cold Spring, NY 10516

6 Bed
5 Baths
3663 sqft
MLS# 1055655
Offered for lease for the first time in more than four decades, this extraordinary country estate presents a rare opportunity to experience the Hudson Highlands from one of Cold Spring’s most distinctive properties.

Set on more than 11 acres, with sweeping views of the Hudson River and Bear Mountain Bridge, the property faces the 50-plus-acre Lane Gate Preserve, part of the Hudson Highlands Land Trust. The setting offers exceptional privacy, space, and connection to the surrounding landscape—all just minutes from the village of Cold Spring.

Warm, expansive, and wonderfully comfortable, the house was designed for gathering. Rich wood and stone appear throughout, including reclaimed 18th-century Massachusetts barn wood that gives the interiors a timeless, character-filled quality. Thoughtfully furnished without feeling formal, the home combines comfort and personality with an easygoing country sensibility.

With 6 bedrooms, 4 full bathrooms, and 1 half bathroom, the home comfortably accommodates up to 16. Multiple living spaces provide room to spread out or come together. A dramatic double-height library adds architectural character, while the main living room features an enormous, sink-in sofa and an impressive, nearly walk-in wood-burning fireplace—an inviting setting for long evenings, movie nights, and conversation around the fire. Working fireplaces are found on three levels, with ample firewood stacked in the carport.

The den is made for fun and relaxation, with a regulation-size pool table that converts to ping pong and a large-screen television. A generous dining table invites lingering meals, while the screened porch serves as an outdoor living and dining room in warmer weather.

From May through September, the grounds truly come alive. A large in-ground Gunite pool and adjacent hot tub are surrounded by the peaceful landscape. Behind the house, a wood-burning fire pit offers an idyllic setting for evenings under the stars. Plentiful parking comfortably accommodates eight vehicles.
Begin the morning with coffee on the screened porch, spend the afternoon beside the pool or exploring nearby trails, and end the day with an unhurried dinner as the sun settles over the Hudson Highlands. Although the setting feels wonderfully removed, many of the region’s finest destinations are remarkably close.

YOUR HUDSON HIGHLANDS BACKYARD

Approximately 5 Minutes — Cold Spring
-Historic Main Street shops, antiques, cafés, and restaurants
-Hudson River waterfront
-West Point Foundry Preserve
-Metro-North station
-Little Stony Point

Approximately 10–15 Minutes — Garrison & Hudson Highlands
-Boscobel House and Gardens
-Constitution Marsh
-Manitoga / The Russel Wright Design Center
-Arden Point
-Anthony’s Nose
-Hudson Valley Shakespeare Festival

Approximately 20–25 Minutes — Beacon & Beyond
-Dia Beacon
-Beacon’s galleries, restaurants, and vibrant Main Street
-Mount Beacon
-Long Dock Park
-Bannerman Castle

Other nearby cultural and culinary destinations include Magazzino Italian Art, the Garrison Art Center, and the Hudson House River Inn.

Whether envisioned as a summer escape, holiday gathering place, extended retreat, or simply somewhere to disconnect and enjoy the Hudson Valley at a gentler pace, 240 Lane Gate Road is an unusually special place to settle in.

A private country estate. A front-row seat to the Hudson Highlands. And, for the first time in more than 40 years, an opportunity to call it home.
Listing by: ONEKEY as distributed by MLS GRID / Listed By: Nicholas Sten, Corcoran Country Living
$9,000 / mo (USD)
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Tivoli Area Rental Home

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42-44 Montgomery Street Tivoli, NY 12583

4 Bed
2 Baths
2136 sqft
MLS# 1049435
In the heart of the village, just a short walk from Tivoli’s restaurants, shops, galleries and Kaatsbaan Dance Center, 42 Montgomery Street is one of the village’s oldest homes—a Folk Victorian dating to 1880, lovingly restored for modern living. From the street, the house retains the quiet dignity and distinctive character of its era. Enter through the original paired entry doors, and the house immediately opens into a light-filled sequence of rooms that feel both historic and remarkably fresh. The gracious front living room flows naturally into a spacious dining room, where an original mahogany built-in cabinet and mirror remain beautifully intact. Contemporary lighting brings a modern sensibility to the room, creating an effortless backdrop for either traditional or contemporary furnishings. Throughout the house, original architectural details have been thoughtfully preserved and paired with clean, modern design elements. Beyond the dining room is a large chef’s kitchen overlooking the long, tree-filled backyard. With quartz countertops, new Bosch Stainless dishwasher, refrigerator and a GE Cafe six burner gas range and hood, custom millwork cabinetry and generous workspace, the kitchen is designed as much for gathering as it is for cooking. French doors lead easily to the back porch and patio, extending the living space outdoors for long summer lunches, evening drinks and al fresco dinners. The first floor also includes a half bath and a second spacious, sunny living area overlooking the side garden. Original details—including an old coal stove—offer quiet reminders of the home’s earlier life, while updated lighting, finishes and new central heating and air conditioning throughout bring the house comfortably into the present. Upstairs, a long hallway leads to four inviting bedrooms, many of which with built-ins: shelving, closets and seating. A dedicated laundry room with washer and dryer adds everyday convenience, while the full bath combines historic character with modern luxury: a deep soaking claw foot cast-iron tub, walk-in Brassna Thermostatic shower, handmade Zia tile and bespoke Francone brass fixtures echo the craftsmanship of the house. Outside, generous side and rear gardens are framed by mature trees and planted with flowering perennials that unfold throughout the seasons. There is room here for gardening, outdoor dining, entertaining or simply enjoying the particular pleasure of a village house surrounded by old growth trees and lawn. Dinner is one block away. Bard College, Red Hook and the Taconic Parkway are a short drive, with Hudson and Rhinebeck both easily accessible. Set within the Hudson Valley’s landscape of farms, rivers, historic villages and cultural destinations, yet less than two hours from New York City, 42 Montgomery Street offers something increasingly rare: the chance to live inside a piece of village history without giving up the ease and beauty of modern life. A gracious old house, thoughtfully renewed—and ready for its next chapter.
Listing by: ONEKEY as distributed by MLS GRID / Listed By: E. Elizabeth Peters, Corcoran Country Living
$4,200 / mo (USD)
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Rhinebeck Area Rental Property

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21 Cramer Rhinebeck, NY 12572

3 Bed
3 Baths
2487 sqft
MLS# 20265631
Discover comfortable Hudson Valley living in this charming contemporary home, ideally located just outside the heart of Rhinebeck in a peaceful dead-end neighborhood. Set on a beautifully maintained property, the home offers a wonderful sense of privacy and tranquility while remaining convenient to everything Rhinebeck has to offer. Step inside to a bright and inviting main level featuring soaring cathedral ceilings and an open floor plan that creates an airy, welcoming atmosphere. Sliding glass doors provide easy access to the front deck, while a screened-in rear porch offers the perfect spot for morning coffee, outdoor dining, or simply relaxing and enjoying the surrounding natural setting.
The main level also features a comfortable bedroom and full bathroom, providing flexibility for guests, a home office, or additional living space. Upstairs, the privately situated primary bedroom offers a peaceful retreat complete with its own ensuite bathroom.
The walk-out lower level adds even more usable space, with multiple rooms that can accommodate a variety of needs, whether you're looking for a home office, recreation area, workout space, or additional storage. A private sauna provides the perfect place to unwind at the end of the day. The kitchen is both functional and inviting, featuring stainless steel appliances and ample cabinetry. Hardwood and ceramic tile flooring throughout the home complement its contemporary character while offering easy everyday living.An attached two-car garage provides protected parking along with valuable additional storage. Offering privacy, flexible living spaces, and a desirable location just minutes from the Village of Rhinebeck, this thoughtfully designed home is an inviting place to settle in and enjoy the Hudson Valley lifestyle.
Listing by: Hudson Valley Catskills MLS / Listed By: Danielle Marchisella, Corcoran Country Living
$4,200 / mo (USD)
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Rhinebeck Area Rental Home

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21 Cramer Road Rhinebeck, NY 12572

3 Bed
2 Baths
2487 sqft
MLS# 1053904
Discover comfortable Hudson Valley living in this charming contemporary home, ideally located just outside the heart of Rhinebeck in a peaceful dead-end neighborhood. Set on a beautifully maintained property, the home offers a wonderful sense of privacy and tranquility while remaining convenient to everything Rhinebeck has to offer. Step inside to a bright and inviting main level featuring soaring cathedral ceilings and an open floor plan that creates an airy, welcoming atmosphere. Sliding glass doors provide easy access to the front deck, while a screened-in rear porch offers the perfect spot for morning coffee, outdoor dining, or simply relaxing and enjoying the surrounding natural setting. The main level also features a comfortable bedroom and full bathroom, providing flexibility for guests, a home office, or additional living space. Upstairs, the privately situated primary bedroom offers a peaceful retreat complete with its own ensuite bathroom. The walk-out lower level adds even more usable space, with multiple rooms that can accommodate a variety of needs, whether you're looking for a home office, recreation area, workout space, or additional storage. A private sauna provides the perfect place to unwind at the end of the day. The kitchen is both functional and inviting, featuring stainless steel appliances and ample cabinetry. Hardwood and ceramic tile flooring throughout the home complement its contemporary character while offering easy everyday living.An attached two-car garage provides protected parking along with valuable additional storage. Offering privacy, flexible living spaces, and a desirable location just minutes from the Village of Rhinebeck, this thoughtfully designed home is an inviting place to settle in and enjoy the Hudson Valley lifestyle.
Listing by: ONEKEY as distributed by MLS GRID / Listed By: Danielle Marchisella, Corcoran Country Living
$3,500 / mo (USD)
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Pine Plains Area Rental Home

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82 Lake Road Pine Plains, NY 12567

4 Bed
3 Baths
2040 sqft
MLS# 1030880
A Home with a view of Stissing Mountain! Enjoy gorgeous sunsets all year long from your front door. Spacious raised ranch on a level lot is move-in ready. Main floor has an open floorplan and wood floors throughout. The light filled kitchen with a nice sized island has new granite countertops. The storage room next to the kitchen could easily become a walk-in pantry. Primary bedroom has en-suite bath. A second hallway full bath is conveniently located for use by the other two bedrooms. First floor also has guest quarters that include a bedroom, half bath and sitting room or office. Finished basement with a gas fireplace for those chilly winter nights at home with family. An additional room that could be for gaming, office or den. Completing the lower level is a separate room for laundry. There is also a one car garage and an unfinished bonus room waiting for you to make it special to you. Plenty of yard space for outdoor activities and BBQs. Driveway has room for plenty of off-street parking. Quiet road conveniently located near the town park – beach, kayaking, playground, large pavilion, picnic area, etc. A short distance to Thompson Pond Nature Preserve, plenty of hiking trails including a trail up to the Stissing Fire Tower. Less than a mile from village center with its quaint shops and eateries – dine at The Stissing House or get pizza or burgers and don’t forget to visit the Stissing Cultural Center for a concert or a play. Come take a look!
Listing by: ONEKEY as distributed by MLS GRID / Listed By: Michelle Francese, Corcoran Country Living
$3,100 / mo (USD)
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Millerton Area Rental Home

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691 Smithfield Road Millerton, NY 12546

2 Bed
2 Baths
2211 sqft
MLS# 1058719
AVAILABLE November 15, 2026. Fully furnished, this circa 1790 eyebrow farmhouse is cozy, comfortable and move-in ready. It is nicely situated on bucolic Smithfield Road in Millerton, NY. Meticulously maintained, the original details, moldings, beams, doors, and flooring are stunning. There is mostly original red pine flooring throughout. The central air-conditioning adds a great modern amenity. The windows are all thermal paned; some of them brand new. The enclosed porch entrance is welcoming and useful. Another wrap around deck features a hanging swing bench and continues to the rear with lighting and dining table and chairs. Inside on the main level is the beamed ceiling living room with propane fireplace, and open windowed country kitchen + dining with decorative vintage fireplace with wooden trim and mantle. A home office and full bath with 6 foot soaking tub is also on this floor. Upstairs are the bedrooms; one with a double bed and one king. Another full bathroom with shower, and linen closet is also on this level. Rough horse boarding is also available at this property. NO PETS. Does not include linens and towels. Landord pays for propane for hot water and cooktop and heat. If pricing soars, there may be an extra charge. This is all nearby to the charming shopping and dining village of Millerton, which features a cycling Rail Trail. Also closeby are the towns of Rhinebeck, Millbrook, Sharon, CT and more. Nature and recreation are abundant! Welcome to the Hudson Valley.
Listing by: ONEKEY as distributed by MLS GRID / Listed By: Steve Bruman, Corcoran Country Living