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Holiday Homes in New Windsor

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    Don't let other travellers get your favourite New Windsor area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 17 Rentals in New Windsor
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    The following rentals are within 15 kilometres of New Windsor.
    Beautiful 4 br in historic Cold Spring!1 / 24
    (4)Excellent
    Cold Spring
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Earth Berm House at Terra Casa Retreat Center1 / 11
    (5)Very good
    Plattekill
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Our Rockbound Highland Home * 2 Blocks to West Point * 1/2 Block to Main St1 / 12
    (3)Excellent
    West Point
    3 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    Beacon
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Porch
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On a quiet dead end street leading to an abandoned bridge over Fishkill Creek, this idyllic brick period charmer has a quaint Mansard roof and dormered windows. Antique carriage lamps adorn the facade. Exposed wood beams and hardwood floors throughout. Exquisite attention to detail is what makes...
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    Beacon, New York 12508
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    50 Mins from  Manhattan River view1 / 19
    (4)Excellent
    Cornwall on Hudson
    5 Bedrooms, 3 Bathrooms, Sleeps 17 Quick View
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    • Mountain Views
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Washer
    • Patio
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 June 2017
    We rented this for West Point Graduation and had 13 people staying at the house. Great layout made for plenty of room for all & places to gather. We couldn't have asked for...
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    About this property
    We are 60 minutes from Manhattan ..yet totally secluded . Heated in ground swimming pool Lots of historic things to see here . Also can rent kayaks to cruise the River 20 Minutes from Woodbury Commoms world famous out let stores. Huge fire place and skiing near by. Walking distance to places...
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    Cornwall on Hudson, Cornwall 12520
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 17
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    Keith's Classic Film Retreat1 / 12
    (2)Very good
    Newburgh
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Waterfront
    • Patio
    • Secure Parking
    • Hot Tub
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 July 2017
    We stayed at Keith's place for two nights while visiting West Point. Beautiful home, lovingly decorated with antiques and in an Old Hollywood theme. Keith was very gracious. He...
    Reviewed 14 July 2016
    This place was beautifully decorated, and the bedroom was really nice and spacious with a great mattress. We only stayed one night for a wedding so didn't explore the area much...
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    About this property
    I am offering a 1912 lovely foursquare home overlooking historic Downing Park and pond ( private second floor with bedrooms and bath.... dinning room available). Home has most of it's original details. Home is filled with original artwork and Hollywood memorabilia. Newburgh is the second largest...
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    Newburgh, New York 12550
    Private Room - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Fort Montgomery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Secure Parking
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Fort Montgomery, New York 10922
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Cold Spring
    5 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come relax and refresh and recharge in our little slice of heaven just an hour and a half north of the city, outside the bucolic town of Cold Spring on the Hudson. We built it in 1995 on five acres of woodland, nestling the house in the hillside with the adjacent pool in a woodland glade, and a...
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    Cold Spring, New York 10516
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 9
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    Garrison
    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A majestic private setting, cozy & chic cabin, a beautiful country home, minutes from the Garrison train station, West Point and 75 min to NYC. The town of Garrison borders Cold Spring, NY, offering a selection of restaurants as well as a myriad of hiking and trails. Beacon and Peekskill are a...
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    Garrison, New York 10524
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
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    Newburgh
    3 Bedrooms, 2 Bathrooms, Sleeps 3 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It's a beautiful neat stable home, smoke free for a big family even children is able, must leave house the way we left it, neat and clean environment. You will be provided with free food as well, clean sheets, clean rest room, free pool area in the backyard with an indoor jacuzzi you will love it...
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    Location Information
    Newburgh, New York 07666
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 3
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    Marlboro
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Housekeeping Included
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large 3 bedroom first floor house located on top of a hill in a quiet neighborhood. Home owned by family for over 40 years. - Owner will rent for 7-120 days at 1st, after the renter will be able to renew the lease if they choose & if owner approves. The Space Looking to rent the first floor of a...
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    Marlboro, New York 12542
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Villa 9W - Hudson Valley Luxury Vacation Home1 / 59
    (2)Excellent
    Newburgh
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Washer
    • Grill
    • Mountain Views
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 May 2018
    Max and Dino are amazing hosts! They made our stay such a special experience. Great communications, and superior hospitality throughout. The house is exceptionally beautiful in...
    Reviewed 15 May 2018
    This is one of a kind home designed by Duncan Avenue Design Studio - Hudson Valley's premier Real Estate Developer and Award Winning Team of Designers featured New York State of...
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    About this property
    Welcome to the Villa 9W: a beautiful vacation home and a perfect summer destination, designed by the Award-Winning Duncan Avenue Design Studio and featured in the Hudson Valley Style Magazine. Located in the heart of the Hudson River Valley just minutes to World-Class Travel Destinations such as...
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    Location Information
    Newburgh, New York 12550
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Garrison
    5 Bedrooms, 3 Bathrooms, Sleeps 15 Quick View
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    Amenities & Details
    • Patio
    • DVD Player
    • Sauna
    • Washer
    • Hot Tub
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Do you have a special Birthday ? Anniversary? How about a work retreat ? or do you want a break from the concrete jungle ? This charming 1910 farmhouse is perfect for resting, relaxation, restoring. It is fantastic for preparing meals as a group and having a decadent dinners with close friends...
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    Garrison, New York 10524
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 15
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    Beacon
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Grill
    • Central Heating
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy an entire house in Beacon- spacious and newly refurbished preserving the classic 1950s mid century style. The front porch is great for morning coffees and the backyard is fenced in. Walking to the Metro North train station and Main Street. Beacon offers so much to do - hiking through the...
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    Beacon, New York 12508
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Base Camp - Dutch Colonial Estate
    Beacon
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private getaway at the base of Mt. Beacon. Easy access to hiking trails and walking distance to downtown Beacon. Views of the Hudson Valley from the front exposure, and mountains to the rear. Large airy bedroom with a beautiful tiled bath. The Space The maid's wing of our brick Dutch colonial...
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    Beacon, New York 12508
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Garrison
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Easy access to train, hiking, recreation, river Charming 2 bedroom cottage Easy access to New York City as well as recreational areas in the region. Beautiful environs, lots of trees, birds, mostly quiet. Home bright with daylight Air conditioned 10 minutes from Cold Spring 20 minutes to Beacon
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    Garrison, New York 10524
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Fishkill
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note that the homeowner lives on site, in a completely separate unit, and may be present during your stay. ** Enjoy your visit to the Hudson Valley during your stay in this 1-bath vacation rental studio apartment in Fishkill. The cozy studio is perfect for a romantic getaway for 2 and...
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    Location Information
    Fishkill, New York 12524
    Condo/Apartment - 1 Bathroom, Sleeps 2
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