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Holiday Rentals in Peekskill

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    All 30 Rentals in Peekskill
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    The following rentals are within 25 kilometers of Peekskill.
    Relaxing Modern Retreat1 / 18
    (7)Very good
    Lake Peekskill, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Cold Spring Lake Hideaway1 / 13
    (5)Excellent
    Cold Spring, NY
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Beautiful 4 br in historic Cold Spring!1 / 24
    (4)Excellent
    Cold Spring, NY
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Keith's Classic Film Retreat1 / 12
    (2)Very good
    Newburgh, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Patio
    • Secure Parking
    • Hot Tub
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 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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    Beacon, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
    • Patio
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    All the comforts of home smack dab in the middle of all the best that Beacon has to offer. This airy 1920s bungalow is 3 blocks from cafe's, antique shops, and great restaurants on Main St. There is a fireplace, large eat-in kitchen, 6 person dining table, brand new bathroom, great backyard and...
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    Beacon, New York 12508
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Beacon, NY
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Grill
    • Internet Access
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Porch
    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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    Mount Kisco
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated at the end of a quiet, semi-private road, this delightful Country Retreat offers a tranquil and serene experience for your vacation stay. The lush trees will embrace you and offer a sense of seclusion, yet the wide-open space allows for wandering eyes to breathe in the stunning views of...
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    Mount Kisco, Westchester County 10549
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Nature, Art, Hip Hudson Valley River Town 70mi NYC1 / 23
    (1)Very good
    Beacon, NY
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Patio
    • Air Conditioning
    • Grill
    • Porch
    • DVD Player
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PLEASE NOTE: I DO NOT RENT FOR FOR 1 NIGHT. THERE IS A 2 NIGHT MINIMUM. Continue reading further down in this box for 5***** Reviews. Here's a sample: 'More like a boutique hotel.' 'This house is a dream come true.' 'Great owner, great location!' This home in beautiful Hudson Valley is a...
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    Beacon, New York 12508
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Fort Montgomery, NY
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly created spacious 1 Bedroom apartment in historic Fort Montgomery NY. Minutes to West Point, Bear Mountain and many other historic sites. Nestled in the heart of the Hudson highlands we are situated amongst some of the Hudson valley's most scenic and historic sites in NY State. Access is easy...
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    Fort Montgomery, New York 10922
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    50 Mins from  Manhattan River view1 / 38
    (4)Excellent
    Cornwall on Hudson, NY
    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 3 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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    Fort Montgomery, NY
    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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    Garrison, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Cable/satellite TV
    • Private Garden
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our 1400 sq. ft. Saltbox style home was built in the early 1980's. It sits on 2.25 acres. with each room having a view of the garden that surrounds the house. Our road is a neighborhood of friends, young and old. In an hour we can be at the top of a mountain looking down on the Hudson River and...
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    Garrison, New York 10524
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beacon, NY
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming and cozy mini apartment with a private entrance, west end of Beacon. Steps from historic Main Street, shopping and Metro North train station. My place is good for couples, solo adventurers, and business travelers. Quiet residential neighborhood just off Main Street close to galleries,...
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    Beacon, New York 12508
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Chappaqua
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Parking
    • Balcony
    • Air Conditioning
    • Internet Access
    • Shared Garden
    • Outdoor Dining Area
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The cottage at Stone Croft is a quick train ride to Manhattan, but looks out on woods and a stream. The cottage is like a two story suite with a full kitchen. There is a queen bed in the main bedroom and a queen sofa bed upstairs. A great place for families and kids. There is a dishwasher,...
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    Chappaqua, Westchester County 10514
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Orchard Hill Estate: Retreat, Reunions, Near West Point, NYC, Hot tub, ski relax1 / 58
    (1)Very good
    Monroe, NY
    7 Bedrooms, 5 Bathrooms, Sleeps 23 Quick View
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    • Washer
    • DVD Player
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Orchard Hill Estate is a gem with breathtaking views of spectacular sunrises and sunsets. There is plenty of space, allowing you to relax in style with your friends and family for the holidays or a getaway. Events and weddings can be held for an additional charge (ask about wedding packages and...
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    Monroe, New York 10926
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 23
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    Pomona, NY
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
    • Grill
    • Washer
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to 'THE HILLTOP' NOT READY FOR SUMMER'S END?? EXTEND YOUR SUMMER SEASON AT 'THE HILLTOP' POOL OPEN TIL END OF SEPT W/ WARM WATER!!!! BOOK YOUR WEEKEND/WEEKLY SEPT STAY NOW Rockland County 6000 sq ft Country Estate with Modern Flair on 1 acre of secluded grounds. This...
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    Pomona, New York 10970
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Base Camp - Dutch Colonial Estate
    Beacon, NY
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • 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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    New Windsor, NY
    20 Bedrooms, 25 Bathrooms, Sleeps 50 Quick View
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    • Private Garden
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Camp grounds, beautiful and serene. Can reserve groups of up to 210 campers. Private lake, retreats, hiking trails, archery, biking, fishing, rock wall climbing, zip line, canoeing, swimming, basketball, soccer, football, tennis, horse back riding, baseball, sand volleyball, meditation, arts &...
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    New Windsor, New York 13865
    Holiday Rental House - 20 Bedrooms, 25 Bathrooms, Sleeps 50
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    New City, NY
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully renovated gorgeous large two bedroom apartment, in an elevator building, featuring one room with a queen and a full size bed size in the other bedroom one full one twin . It features a high quality sofa beds, hard wood floors, large windows and a dining area for four. The living area, with a...
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    New City, New York 10065
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Lakewood Estate; Private & tranquil- less than one hour to NYC, sleeps up to 241 / 22
    (2)Excellent
    Croton on Hudson
    8 Bedrooms, 7 Bathrooms, Sleeps 24 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Washer
    • Patio
    • DVD Player
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    This site was truly amazing. The accommodations were beyond expectations. The home has a very friendly warm feeling. There were seventeen of us and each party had their own...
    Reviewed 1 week ago
    We were looking for a house that would be large enough for our family and we booked Greta's place. The house was fantastic! It had 8 unique bedrooms each with period furniture...
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    About this property
    Secluded and private on over 100 protected acres, this historically significant 1800's estate boasts a good amount of extras. Private tennis court, hiking trails, fishing, golf course (4 miles away), and your own farmhouse. Meticulously maintained, each room is tastefully decorated and immaculate....
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    Croton on Hudson, Westchester County 10520
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 24
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    Cortlandt Manor
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Porch
    • Grill
    • Mountain Views
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is an independent room with separate access. The room is fully furnished with a queen bed, breakfast table, couch, Cable TV and internet. The room also has a separate kitchen and a shared laundry. The guests are allowed to cook with an electric /induction stove.Two miles from Annesville creek...
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    Cortlandt Manor, Cortlandt 10567
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Newburgh, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 3 Quick View
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    • 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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    Newburgh, New York 07666
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 3
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    Caren House Bed and Breafast1 / 5
    (1)Excellent
    Monroe, NY
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • DVD Player
    • Porch
    • Shared Garden
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Caren House Bed and Breakfast is located 3 miles from Woodbury Commons Premium Outlets in Harriman, NY. We provide transportation to and from the Commons. We are also close to West Point Military Academy, a Jack Nicklaus Golf Course, the Applachian Trail, wineries, Orange County Choppers. We are...
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    Monroe, New York 10950
    Private Room - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Croton on Hudson
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Mountain Views
    • Grill
    • Balcony
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The apartment is attached to the main house with a separate,private entrance. The apartment exits onto a patio next to the pool. It has a living room, bathroom and kitchen. Fully furnished. It is located on 3 acres of lawn and woodland. It is quiet. We are 48 minutes by train from mid...
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    Croton on Hudson, Westchester County 10520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Croton on Hudson
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Waterfront
    • Mountain Views
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For the adventurers who want to go camping, but don't want to buy hundreds of dollars worth of expensive equipment and might not have the vehicle to carry it all! Everything you will ever need for an amazing camping experience is provided for you! It will all be set up prior to your arrival and...
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    Croton on Hudson, Westchester County 10520
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Pomona, NY
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Parking
    • Mountain Views
    • Private Garden
    • Housekeeping Included
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy cabin, with outdoor fire pit, bordering up with Harriman State Park. This is an ideal location for all those nature and hike lovers. There is a stream that flows in the back of the property that comes from the surrounding mountains, with a close entrance to one of the parks hiking trails. This...
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    Pomona, New York 10980
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Nyack, NY
    5 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Overlooking the magnificent Hudson River in Nyack, New York, this 6,500 square foot Italianate Victorian Estate is recognized as a historical landmark for its architectural beauty, scenic location, and famous residents. Built in 1858, this picturesque home was bought by actress Helen Hayes and...
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    Nyack, New York 10960
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 9
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    New City, NY
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful private bedroom which is self contained.The bathroom is large with 2 sinks.It is a shared bathroom with 1 other room..There is a fridge ,microwave and coffee maker and kettle.Free Wifi.Free towels,Free line free satellite Tv..Everything you need for a comfortable stay at an affordable...
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    New City, New York 10035
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    New City, NY
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Sauna
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A residence-style Boutique Hotel, the Manhattan Club provides endless possibilities for the enjoyment of its guests. The Manhattan Club introduces a unique experience; blending a vacation ownership retreat with a luxury suite hotel. Centrally located in midtown Manhattan, it is convenient to many...
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    New City, New York 10019
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Nyack, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
    • Grill
    • Housekeeping Included
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Twenty minutes Twenty minutes to Manhattan. Private two bedroom lower level of a house not a basement. It has its own entrance, kitchen, bathroom, fire place and washer and dryer. Plenty of parking in a private driveway. Mass transit is walking distance.Also close to the Palisades mall, bear...
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    Location Information
    Nyack, New York 10994
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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