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$20,000 / mo (USD)
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Rhinebeck Area Rental Home

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36 Pilgrims Progress Road Rhinebeck, NY 12572

3 Bed
4 Baths
3478 sqft
MLS# 991649
Perched at the top of a long winding drive and surrounded by woodland, this stunning new construction offers something genuinely rare: the feeling of a true country escape with the restaurants, shops, and culture of Rhinebeck just a four-minute drive away. The setting has a way of making the outside world feel very far off. Inside, the open layout was built for the way people actually want to spend a weekend together. The kitchen is a showpiece outfitted with an 8-burner Wolf range with pasta water spout, Sub-Zero appliances, a granite island, and a dedicated bar with ice maker. Someone is always cooking, someone is always catching up, and the two-sided gas fireplace keeps the whole group connected as the space flows into a soaring living room with vaulted ceilings and floor-to-ceiling picture windows that frame the trees. When the evening calls for it, a covered outdoor room just off the dining area extends the party outside with a mounted TV and surrounding heaters. The whole home runs on Sonos throughout — wired for both indoor and outdoor use, so the music follows you seamlessly from the kitchen to the back deck. Upstairs, an open loft with beamed ceilings and skylights serves as a luxurious media room, giving every group the gift of two living spaces at once: one group disappears upstairs with a movie while the others settle into the living room below, or the early risers grab coffee and the loft while everyone else sleeps in. The primary suite features an en suite bath with dual-head rain shower, steam, heated tile floors, and a TOTO Washlet smart toilet. A private rooftop deck just off the upper hallway offers two lounge chairs and a front-row seat to the sunset. On the first floor, a king bedroom opens via glass doors to the backyard fire pit, and a twin bedroom shares a full bath with double vanity. The surrounding countryside offers a beautiful country road for walking with sweeping mountain views, and local hiking areas are close by for those who want to earn their breakfast. A hot tub, outdoor shower, and sun deck round out the outdoor amenities. The basement will be equipped with a combination pool and ping pong table, and the home includes a one-car garage with interior access. For those arriving without a car, the Rhinecliff Amtrak station is nine minutes away, with direct service to New York City's Moynihan Train Hall in approximately one hour and 45 minutes. The city feels close enough to be convenient and far enough away to forget about it entirely. Offered for seasonal rental beginning May 15, 2026, on a month-to-month basis through 2026 and into 2027. Inquire for availability.
Listing by: ONEKEY as distributed by MLS GRID / Corcoran Country Living / Alexis Li
$20,000 / mo (USD)
Active

Rhinebeck Area Rental Property

Active

36 Pilgrims Progress Rhinebeck, NY 12572

3 Bed
4 Baths
3478 sqft
MLS# 20262032
Perched at the top of a long winding drive and surrounded by woodland, this stunning new construction offers something genuinely rare: the feeling of a true country escape with the restaurants, shops, and culture of Rhinebeck just a four-minute drive away. The setting has a way of making the outside world feel very far off. Inside, the open layout was built for the way people actually want to spend a weekend together. The kitchen is a showpiece outfitted with an 8-burner Wolf range with pasta water spout, Sub-Zero appliances, a granite island, and a dedicated bar with ice maker. Someone is always cooking, someone is always catching up, and the two-sided gas fireplace keeps the whole group connected as the space flows into a soaring living room with vaulted ceilings and floor-to-ceiling picture windows that frame the trees. When the evening calls for it, a covered outdoor room just off the dining area extends the party outside with a mounted TV and surrounding heaters. The whole home runs on Sonos throughout -- wired for both indoor and outdoor use, so the music follows you seamlessly from the kitchen to the back deck.
Upstairs, an open loft with beamed ceilings and skylights serves as a luxurious media room, giving every group the gift of two living spaces at once: one group disappears upstairs with a movie while the others settle into the living room below, or the early risers grab coffee and the loft while everyone else sleeps in. The primary suite features an en suite bath with dual-head rain shower, steam, heated tile floors, and a TOTO Washlet smart toilet. A private rooftop deck just off the upper hallway offers two lounge chairs and a front-row seat to the sunset. On the first floor, a king bedroom opens via glass doors to the backyard fire pit, and a twin bedroom shares a full bath with double vanity. The surrounding countryside offers a beautiful country road for walking with sweeping mountain views, and local hiking areas are close by for those who want to
earn their breakfast. A hot tub, outdoor shower, and sun deck round out the outdoor amenities. The basement will be equipped with a combination pool and ping pong table, and the home includes a one-car garage with interior access. For those arriving without a car, the
Rhinecliff Amtrak station is nine minutes away, with direct service to New York City's Moynihan Train Hall in approximately one hour and 45 minutes. The city feels close enough to be convenient and far enough away to forget about it entirely. Offered for seasonal rental beginning May 15, 2026, on a month-to-month basis through 2026 and into 2027. Inquire for availability.
Listing by: Hudson Valley Catskills MLS / Corcoran Country Living / Alexis Li
$19,500 / mo (USD)
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Woodstock Area Rental Home

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55 Nordic Drive Woodstock, NY 12498

4 Bed
2 Baths
1499 sqft
MLS# 970832
*SUMMER & FALL RENTAL* (AVAIL May 25 - Oct 31, 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 sanctuary where thoughtful design meets sweeping mountain views. A winding private road leads to this peaceful retreat, where the expansive backyard opens to a landscape that feels like your own boutique countryside escape. Outdoors is where the property truly shines. A heated gunite infinity-edge saltwater pool appears to spill into the mountain horizon, surrounded by lounge chairs and wide-open views. Nearby, a cedar sauna, outdoor shower, and hot tub create a spa-like setting beneath the trees. As evening settles in, string lights glow overhead and gatherings naturally form around the stone fire pit while the mountains fade into twilight. The grounds invite both play and relaxation, with a compact soccer field, hammock, outdoor grill and dining area, and multiple lounge spaces designed for long, easy summer days. The property features two thoughtfully designed structures. The main house is a warm three-bedroom retreat that evokes the charm of a boutique mountain lodge. At its center is a spa-inspired bathroom with a steam shower, offering a calming sanctuary after a day outdoors. The European-inspired kitchen features custom cabinetry and a hidden coffee station tucked behind sliding doors, while the living room's wood-burning fireplace opens onto the deck, creating an effortless connection between indoors and out. In the warmer months, the main deck becomes a true outdoor living room. A large dining table, gas BBQ, and relaxed lounge seating surround a wood-burning outdoor fireplace that frames uninterrupted mountain views. Just steps away, a built-in hot tub offers the perfect vantage point for sunset soaks above the treetops. The main home includes three bedrooms: a primary bedroom with a queen bed, a second bedroom with a full-size bed, and a bunk room with twin beds, along with a dedicated laundry room for longer stays. Just beyond the main house sits a separate loft guest house that offers a peaceful retreat of its own. The loft includes a queen bed on the main level and two additional queen beds on the upper level accessed by ladder, along with an optional twin bed on the ground floor. A private deck overlooks the property's open grounds and surrounding mountain scenery. Additional conveniences include two covered parking spaces along the private road and a dedicated electric vehicle charging station. Close to the restaurants, galleries, and music of Woodstock, yet surrounded by fresh mountain air and wooded privacy, 55 Nordic Drive offers a rare Catskills escape designed for both relaxation and gathering.
Listing by: ONEKEY as distributed by MLS GRID / Corcoran Country Living / Alexis Li
$19,500 / mo (USD)
Active

Woodstock Area Rental Property

Active

55 Nordic Woodstock, NY 12498

4 Bed
2 Baths
1499 sqft
MLS# 20260931
*SUMMER & FALL RENTAL* (AVAIL May 25 - Oct 31, 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 sanctuary where thoughtful design meets sweeping mountain views.
A winding private road leads to this peaceful retreat, where the expansive backyard opens to a landscape that feels like your own boutique countryside escape. Outdoors is where the property truly shines. A heated gunite infinity-edge saltwater pool appears to spill into the mountain horizon, surrounded by lounge chairs and wide-open views. Nearby, a cedar sauna, outdoor shower, and hot tub create a spa-like setting beneath the trees.
As evening settles in, string lights glow overhead and gatherings naturally form around the stone fire pit while the mountains fade into twilight. The grounds invite both play and relaxation, with a compact soccer field, hammock, outdoor grill and dining area, and multiple lounge spaces designed for long, easy summer days.
The property features two thoughtfully designed structures. The main house is a warm three-bedroom retreat that evokes the charm of a boutique mountain lodge. At its center is a spa-inspired bathroom with a steam shower, offering a calming sanctuary after a day outdoors. The European-inspired kitchen features custom cabinetry and a hidden coffee station tucked behind sliding doors, while the living room's wood-burning fireplace opens onto the deck, creating an effortless connection between indoors and out.
In the warmer months, the main deck becomes a true outdoor living room. A large dining table, gas BBQ, and relaxed lounge seating surround a wood-burning outdoor fireplace that frames uninterrupted mountain views. Just steps away, a built-in hot tub offers the perfect vantage point for sunset soaks above the treetops.
The main home includes three bedrooms: a primary bedroom with a queen bed, a second bedroom with a full-size bed, and a bunk room with twin beds, along with a dedicated laundry room for longer stays.
Just beyond the main house sits a separate loft guest house that offers a peaceful retreat of its own. The loft includes a queen bed on the main level and two additional queen beds on the upper level accessed by ladder, along with an optional twin bed on the ground floor. A private deck overlooks the property's open grounds and surrounding mountain scenery.
Additional conveniences include two covered parking spaces along the private road and a dedicated electric vehicle charging station.
Close to the restaurants, galleries, and music of Woodstock, yet surrounded by fresh mountain air and wooded privacy, 55 Nordic Drive offers a rare Catskills escape designed for both relaxation and gathering.
Listing by: Hudson Valley Catskills MLS / Corcoran Country Living / Alexis Li
$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 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 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 / Corcoran Country Living / Alexis Li
$16,500 / mo (USD)
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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 / Corcoran Country Living / Alexis Li
$12,000 / mo (USD)
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Pine Plains Area Rental Home

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231 Lake Road Pine Plains, NY 12567

4 Bed
4 Baths
3029 sqft
MLS# 976124
Ideal Summer Retreat. This 4 bedroom (all ensuite), is a perfect blend of chic furnishings and modern conveniences, located in a quiet lakeside community in the heart of Pine Plains but also removed and private. A stones-throw away from Stissing Pond, where you can swim, launch SUP’s and go fishing for trophy Bass, or take a leisurely bike ride around the lake, 3-5 mile loop (local traffic mostly). If a hike is in order, in the opposite direction from the lake, a short walk with ponds and open vistas, you will find Stissing Mountain (1400’ ft elevation) and Thompson Pond Preserve where you will find several miles of varying hiking trails and challenges that await!
The home sits on over 1.5 acres of lush lawns front and rear with mature landscaping and trees flanking the property for complete privacy except for the abundant wildlife that calls it home. Bright, airy, and furnished immaculately down to the crispy white linens, towels, rugs and furniture. The home also offers a true and enviable office for those pesky Zoom meetings that pop up. A great room and parlor provide ample space for those summer dinner parties with the deck off the living-room providing an extension of entertaining to the outdoors seamlessly. Whole home heating and cooling with warm accent lighting throughout will set the mood for the most discerning palate. The rear of the property abuts a forever view of agricultural reserve with distant mountain and rolling hill views from every room of the home. The attached garage is equipped with all of the fun you could need including a ping pong table, fishing essentials, 2 stand up paddle boards and a pair of high end mountain bikes.
Local Farms and Dairy Farms offer fresh milk, ice cream, butter, as well as organic meats, vegetables, baked goods and essential grocery foods. Just minutes away is the famous Stissing House restaurant and others as well as a pharmacy, liquor store and post. One barely needs to go out but if you do there are plays and concerts at the Stissing Center (minutes away) throughout the season as well as concerts in Tivoli, Shakespeare in Lenox, plays at the Sharon Playhouse to mention just a few with historical houses, galleries and museums too. The train to the city is 25 minutes away and the Taconic Parkway is close by should you need to get to the city. Country Life.. it’s good for you.
If requested, the nursery can be cleared and delivered with a full size bed to serve as a true 4th bedroom.
Come see this home, location, and summer opportunity soon! This is a one-off rental that likely will not come to market again.
Listing by: ONEKEY as distributed by MLS GRID / Corcoran Country Living / Catherine Howard