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Dutchess County, NY Homes for Rent with Pool

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  • /25

    $12,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,600 Sq Ft
    • House for Rent

    194 Pleasant Ridge Rd, Poughquag, NY 12570

    *SUMMER RENTAL*Want to live in the Hudson Valley for the Summer!?Stunning 3-bedroom, 2.5-bathroom (FURNISHED) modernist home on 6 private acres with a gunite pool and breathtaking views.This luxurious retreat features an open floor plan with hardwood floors, expansive windows, and a sleek fireplace. The high-end kitchen includes quartz countertops and a spacious island,

    Agent Photo

    Steven Gray

    Compass Greater NY, LLC

    (845) 497-6866

    194 Pleasant Ridge Rd, Poughquag, NY 12570
  • /21

    $9,500 per month

    • 4 Beds
    • 3.5 Baths
    • 4,746 Sq Ft
    • House for Rent

    72 N Mabbettsville Rd, Millbrook, NY 12545

    This contemporary farmhouse on a sprawling property offers extreme privacy just minutes from the village of Millbrook. North Mabbettsville Road is a coveted location, and this property offers trails for hiking and cross country skiing as well as proximity to a range of outdoor activities. Enjoy peaceful pastoral views from the home's wrap-around porch or relax in the heated pool. This graciously

    Candy Anderson Compass Greater NY, LLC

    72 N Mabbettsville Rd, Millbrook, NY 12545
  • /44

    $25,000 per month

    • 4 Beds
    • 3.5 Baths
    • 4,388 Sq Ft
    • House for Rent

    74 Melville Rd, Hyde Park, NY 12538

    SUMMER RENTAL – Available for the month of July for $25,000. This is an exceptional home on six acres in a bucolic setting, beautifully furnished and ready for summer enjoyment with a heated in-ground pool, tennis court, one bedroom guest house and Level 2 EV charger for electric cars! The main house features 4 bedrooms, 3 1/2 bathrooms, beautiful kitchen with breakfast bar, dining room, covered

    Susan Whalen George T Whalen Real Estate

    74 Melville Rd, Hyde Park, NY 12538
  • /23

    $3,500 per month

    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft
    • House for Rent

    39 Nathan Pierce Ct, Pawling, NY 12564

    Welcome to 39 Nathan Pierce Court – a beautifully updated 3-Bedroom, 2.5 Bath townhouse located in the desirable Deerfield Ponds Community. Offering 1,600 sq ft of thoughtfully designed living space, this home combines modern upgrades with everyday comfort and convenience! The kitchen features stainless steel appliances, generous cabinet space, and a bright eat-in area perfect for casual meals or

    LAUREL MASCIA BHHS Hudson Valley Properties

    39 Nathan Pierce Ct, Pawling, NY 12564
  • /33

    $55,000 per month

    • 6 Beds
    • 7 Baths
    • 12,546 Sq Ft
    • House for Rent

    0 Smithfield Valley Rd, Amenia, NY 12501

    Seasonal Rental $55,000 per month, July, Aug, Sept. This property is also avialble annually for $40,000 per month. One of the finest country houses in the Millbrook area. The remarkable quality & grandeur on 432 acres of prime farm & woodland presents a rare opportunity. Created by an award-winning architect, the Colonial Revival home known as Strathmore, with its Ionic columned porch spanning

    George Langa Houlihan Lawrence Inc.

    0 Smithfield Valley Rd, Amenia, NY 12501
  • /34

    $22,000 per month

    • 4 Beds
    • 3.5 Baths
    • 2,650 Sq Ft
    • House for Rent

    1282 Hollow Rd, Clinton Corners, NY 12514

    Perfectly located on a park like setting between the villages of Millbrook and Rhinebeck, sits Maple Knoll. Twenty-five rolling acres with heated pool, tennis court, walking trails and large fishing pond with boat comprise this rural setting. This warm, stylish home offers four bedrooms, three and one-half baths, living room with fireplace, formal dining room, sun room, kitchen and central air.

    Candy Anderson Compass Greater NY, LLC

    1282 Hollow Rd, Clinton Corners, NY 12514
  • /62

    $18,000 per month

    • 5 Beds
    • 2.5 Baths
    • 3,112 Sq Ft
    • House for Rent

    5 Fulton Homestead Rd, Red Hook, NY 12571

    Discover Fulton Homestead, an exceptional Hudson Valley seasonal retreat, where historic charm meets idyllic upstate living. Set on 85 private acres, this beautifully renovated 1790s historic homestead offers the perfect setting to enjoy the region's peak season in comfort, style, and privacy.The property comes alive during the warm-weather months with abundant forsythia and peonies, verdant

    Jennifer Enloe Four Seasons Sotheby's Int.

    5 Fulton Homestead Rd, Red Hook, NY 12571
  • /30

    $8,000 per month

    • 5 Beds
    • 3.5 Baths
    • 4,171 Sq Ft
    • House for Rent

    29 Fairways Ln, Beacon, NY 12508

    This gorgeous fully furnished 5-bedroom, 3.5-bathroom home in Beacon, New York, offers over three acres of scenic property with breathtaking views of the Hudson River and Mt. Beacon. The home boosts an in-ground pool, formal and casual living spaces perfect for all occasions, a basement with workout space, and a dedicated home office for added convenience. Tenants will be responsible for

    Bethzaida Catalano Exit Realty Connections

    29 Fairways Ln, Beacon, NY 12508
  • /36

    $55,000 per month

    • 6 Beds
    • 8 Baths
    • 8,933 Sq Ft
    • House for Rent

    Unlisted Address

    $55,000 per month in summer. Inquire for pricing for other terms and times. Property spans 389 acres in Ct & NY. The house is located in Connecticut. Complete privacy with 1.8 mile long driveway. Perfect for any high profile person or anyone seeking seclusion yet 10 minutes to town. Perched on the crest of a plateau overlooking panoramic, protected views, West Wind Hill, a bespoke country estate

    Joseph Lorino Brown Harris Stevens HV LLC

    Unlisted Address
  • /26

    $17,000 per month

    • 5 Beds
    • 3.5 Baths
    • 3,625 Sq Ft
    • House for Rent

    90 Mill Rd, Millerton, NY 12546

    Welcome to a timeless piece of history, the Ezra Clark House, believed to be the oldest home in the village of Millerton. Built in 1780, this remarkable estate stands as a testament to centuries of architectural craftsmanship and refined elegance.Step into the main house, where 2,625 square feet of living space awaits. With 3 bedrooms, 2.5 bathrooms, and two inviting living areas, this home

    Brian Hastings Serhant LLC

    90 Mill Rd, Millerton, NY 12546
  • /11

    $3,000 per month

    • 2 Beds
    • 2 Baths
    • 1,460 Sq Ft
    • House for Rent

    48 Skunks Misery Rd, Millerton, NY 12546

    Enjoy the charm of this 2-bedroom cottage in Northeast, a town in Northern Dutchess County, NY. This cozy cottage features hardwood floors, a fireplace with a wood stove insert in the living room, a kitchen with a skylight, a 3/4 bath, and a spacious sunroom that fills with natural light. Enjoy outdoor living and sleep under the stars on platform for glamping. Heated pool for those warm summer

    Arleen Shepley Elyse Harney Real Estate

    48 Skunks Misery Rd, Millerton, NY 12546
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    $40,000 per month

    • 5 Beds
    • 6 Baths
    • 6,743 Sq Ft
    • House for Rent

    176 Schoolhouse Rd, Staatsburg, NY 12580

    SUMMER RENTAL – Available July through Labor Day at $40,000 per month. Quintessential c.1765 country estate in a peaceful and private setting. Escape to the countryside and spend the summer lounging by the heated gunite pool, dining al fresco on the bluestone patio, roasting marshmallows around the firepit, exploring the numerous trails throughout the 154 acres and fishing in the pond. This

    PAULA REDMOND Corcoran Country Living

    176 Schoolhouse Rd, Staatsburg, NY 12580
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