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5-Bedroom Rentals in Dutchess County, NY

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  • /20

    $2,500 per month

    • 5 Beds
    • 1 Bath
    • 1,093 Sq Ft
    • Apartment for Rent

    281 Violet Ave, Poughkeepsie, NY 12601

    Updated three-bedroom apartment, bright and clean. First floor, off-street parking. Close to Marist College, MidHudson Hospital, and the Walkway Over the Hudson. Local shops nearby. Hyde Park School District.

    ABBY JOSIAH KW MidHudson

    281 Violet Ave, Poughkeepsie, NY 12601
  • /35

    $4,500 per month

    • 5 Beds
    • 3 Baths
    • 2,549 Sq Ft
    • House for Rent

    98 S Hamilton St Unit 2, Poughkeepsie, NY 12601

    Charming 5-Bedroom Rental in the Heart of Poughkeepsie!Welcome to this beautifully maintained single-family home offering a total of 5 spacious bedrooms and 3 full bathrooms, perfect for comfortable and flexible living. The main home features 4 bedrooms and 2 bathrooms, with a kitchen that includes laminate flooring, a stylish island, and plenty of room for meal prep and entertaining.

    Virginia Corbett eXp Realty

    98 S Hamilton St Unit 2, Poughkeepsie, NY 12601
  • /39

    $8,000 per month

    • 5 Beds
    • 4.5 Baths
    • 7,200 Sq Ft
    • House for Rent

    Unlisted Address

    Stunning fully furnished 6-bedroom, 4.5-bath estate available for rent in the desirable Old Hopewell Estates of Old Hopewell road. . Set on over 4 private acres in a quiet cul-de-sac, this expansive home offers over 7,000 sq ft of living space with soaring two-story ceilings and abundant natural light. The first floor features a convenient guest suite, while the finished walkout basement includes

    Christian Baez Keller Williams Hudson Valley

    Unlisted Address
  • /21

    $7,750 per month

    • 6 Beds
    • 7 Baths
    • 6,867 Sq Ft
    • House for Rent

    12 Blueberry Hill Rd, Hopewell Junction, NY 12533

    Private Mountain Top Mediterranean Villa ! Almost 7000 sq feet w 6 BRs 6 Baths, Wrap Terrace with Gorgeous Mountain Views, Enormous Patio, 2 Separate Living Spaces each with Separate Entrances and Separate Kitchens, 2 Woodburning Fireplaces, Pets allowed on case by case w deposit, Very Close to Beacon , Metro North Train and Taconic Parkway

    Richard Healy Corcoran Country Living

    12 Blueberry Hill Rd, Hopewell Junction, NY 12533
  • /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
  • /48

    $4,950 per month

    • 6 Beds
    • 3.5 Baths
    • 5,256 Sq Ft
    • House for Rent

    60 Innsbruck Blvd, Hopewell Junction, NY 12533

    Located in the charming and stately neighborhood of “Little Switzerland”, 60 Innsbruck offers incredible space & serenity, with beautiful natural stone and wood throughout, all less than five minutes from the Taconic. Featuring soaring ceilings and walls of glass, fully furnished with perfect mid-Century modern pieces, this home is move-in ready for its next resident to enjoy all the space one

    Claudia Dizenzo Hudson River Line Realty

    60 Innsbruck Blvd, Hopewell Junction, NY 12533
  • /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
  • /45

    $13,000 per month

    • 6 Beds
    • 7.5 Baths
    • 7,460 Sq Ft
    • House for Rent

    259 Woodstock Rd, Millbrook, NY 12545

    YEARLY RENTAL offered for $13,000 per month plus utilities. Peace and tranquility await at this sprawling country retreat. A stream meanders through the 15.37 acre property forming two waterfalls and flows into a deep water pond creating a beautiful lush landscape viewed from many vantage points. This amazing and expansive 7,460 square foot home is comprised of three 18th century structures that

    PAULA REDMOND Corcoran Country Living

    259 Woodstock Rd, Millbrook, NY 12545
  • /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
  • /41

    $10,000 per month

    • 5 Beds
    • 3.5 Baths
    • 5,370 Sq Ft
    • House for Rent

    11 Ridgeview Ln, Pleasant Valley, NY 12569

    Welcome to 11 Ridgeview. Nestled on over 7 private acres in a quiet cul-de-sac, this stunning 5-bedroom, 3.5-bathroom LaGrange home offers elegance, space, and exceptional craftsmanship. A long, gated driveway leads to this custom-built brick estate featuring a grand curved staircase, vaulted ceilings, and gleaming hardwood floors with intricate inlays. The entrance and kitchen area showcase

    Howard Payson RE/MAX Town & Country

    11 Ridgeview Ln, Pleasant Valley, NY 12569
  • /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
  • /19

    $6,900 per month

    • 5 Beds
    • 3 Baths
    • 3,172 Sq Ft
    • House for Rent

    6 Kathy Ct, Fishkill, NY 12524

    Spectacular views less than a 90-min scenic drive to NYC. 5 mins from shopping, restaurants, highways, parks, & trails. This stunning home is gorgeous w/ a modern kitchen, pristine furniture, formal dining rm, large backyard & patio, parking for 4+ cars & three different sections of the home- perfect for quiet time away from the crowd. Don't miss this opportunity to stay at the home foreign

    Andre Galiber Galiber Humphrey Real Estate

    6 Kathy Ct, Fishkill, NY 12524
  • /37

    $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
  • /37

    $5,500 per month

    • 6 Beds
    • 3.5 Baths
    • 4,398 Sq Ft
    • House for Rent

    20 Welwyn Rd, Millbrook, NY 12545

    Beautiful home in a private 14+ acre setting less than 2 miles to the center of the Village of Millbrook. This gracious Center Hall Colonial boasts country elegance throughout. Inside you will find rooms with wonderful proportions and stunning wood floors. Outside, enjoy a lovely patio, landscaped gardens, and a beautiful yard. Included with this rental is a spacious, detached three bay garage.

    Susan Whalen George T Whalen Real Estate

    20 Welwyn Rd, Millbrook, NY 12545
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