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Ossining Vacation Rentals

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    All 30 Rentals in Ossining
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    The following rentals are within 25 kilometres of Ossining.
    Charming and immaculate 3 br duplex!1 / 17
    (7)Excellent
    Greenwich, CT
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Greenwich, CT
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Greenwich, CT
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Relaxing Modern Retreat1 / 18
    (5)Very good
    Lake Peekskill, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Grill
    • Air Conditioning
    • Porch
    • Patio
    • Satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 May 2017
    The location is very close to many restaurants and shopping. The home was very clean. The home is situated on a large piece of property. I went with my grandchildren and they...
    Reviewed 12 January 2017
    Marisol's home was just what we wanted, close to our family for Christmas and near stores. The home was clean with most everything you need to cook and have dinner. The only...
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    About this property
    Perfect relaxing and fun getaway from the city. This updated charming cape is minutes away from the Bear Mountain State Park, Blue Mountain Reservation, FRD State Park and Hollow Brook Golf Club-all offer fun action packed activities. Love shopping? The house is 20mins away from Woodbury Commons...
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    Lake Peekskill, New York 10567
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Mahopac Falls, NY
    4 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    • Secure Parking
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located an hour outside of New York, this stunning 4 bedroom, 3.5 bathroom can be your home away from home for a few nights. The house sits on a picturesque 3 acre property that offers seasonal lake views, and features a private patio with outdoor fireplace to enjoy a summer night outside. The...
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    Mahopac Falls, New York 10579
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 7
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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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    Woodcliff Lake, NJ
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    HSUD322 - Accommodation Cannes : 400m from the Palais des Festivals and Croisette on the 2 floor of a building in centre of Cannes. Shops and restaurants, bus stop, harbour 150 m, sandy beach and rue d'Antibes 300m.Train station 700m Apartment to rent 3 rooms of 75 m² : living/dining room with...
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    Woodcliff Lake, New Jersey 07677
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tuckahoe
    3 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Wi-Fi
    • Satellite TV
    • Parking
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunny, spacious and comfy 3 bedroom apartment with balcony . Walk to train is 2 minute . Seriously it's 2 minute to the train to NYC. Starbucks located in train station . Bars, banks , cafes, and hospital all 5-10 walking distance on safe roads with sidewalks and pedestrian crosswalks. Can also...
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    Tuckahoe, Westchester County 10707
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 4
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    NYC Midtown 30 minutes-Scarsdale on Golf Course1 / 23
    (3)Excellent
    Scarsdale
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Balcony
    • Patio
    • DVD Player
    • Grill
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 June 2017
    This is a beautiful house and perfect for large family gatherings. Our family was in Hartsdale to celebrate a 50th anniversary. Most of my adult siblings and a young adult...
    Reviewed 18 June 2015
    This house was exactly as pictured and described. It was extremely clean, light, airy and well appointed and Anne was very nice and quite helpful with our trip. The air...
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    About this property
    Beautiful sunny spacious home located on a private cul-de-sac providing a tranquil and quiet setting . Two master bedroom suites with own master baths. Master bedroom has a deck which overlooks the golf course. Cathedral ceilings throughout, family room with 60 inch smart flat screen TV, french...
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    Scarsdale, Westchester County 10583
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    Greenwich, CT
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Parking
    • Patio
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Greenwich, Connecticut 06831
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Elegant, Newly Renovated 5 Bedroom Home1 / 25
    (3)Very good
    White Plains
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Shared Garden
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 June 2015
    This is an older home that has been refurbished and is presently in good condition. There are three levels of stairs and the hand railing on each landing is secure but low. The...
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    About this property
    Only 30 minutes away from New York City this gorgeous vintage duplex home from the 1920's that has stayed within the family for many generations. It has been fully renovated as of late January 2015 from top to bottom and includes some new appliances and furniture. It is a 3 story house with high...
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    White Plains, Westchester County 10606
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    New City, NY
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Satellite TV
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    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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    Greenwich, CT
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With my children off to college I have an empty 3rd floor (so availability is around the school calendar). Neat 3rd floor unit with its own bedroom, separate sitting room, small fridge, microwave, coffee-maker, bathroom (stall shower), TV, and table for 4. Ideal for someone working weekdays in...
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    Greenwich, Connecticut 06830
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Greenwich, CT
    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Balcony
    • Air Conditioning
    • Washer
    • Patio
    • Wi-Fi
    • Porch
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming 4 bedroom home at the end of a quiet country lane on a horse farm. Country kitchen with a lovely patio and grill. Heated and cooled with recently installed geothermal enjoy peace and tranquility in a beautiful setting. Horses live on the property, please inquire about lessons or trail...
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    Greenwich, Connecticut 06831
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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    Greenwich, CT
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Satellite TV
    • Washer
    • Air Conditioning
    • Balcony
    • Terrace
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious and elegant three bedroom, two and one half bath, 1,900 SF condominium built in 2003. The first floor offers a large living room with two exposures, a gourmet eat-in kitchen with sliding doors that access an outdoor sitting area and garden. The generous master bedroom with en-suite bath is...
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    Greenwich, Connecticut 06830
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Greenwich, CT
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Washer
    • Satellite TV
    • Parking
    • Grill
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Lauren Berger Collection is proud to be recognized as one of the best Vacation Rental companies in the world by the best, The Vacation Rental Guide. A forty-five minute drive from Manhattan but a world away from the clamor, this serene, elegant home is set on an acre of rolling lawns in one...
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    Greenwich, Connecticut 06830
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Pound Ridge
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A luxury cottage set privately on a 7 acre estate in sylvan Pound Ridge, New York. A perfect setting from which to explore Westchester's horse country, The Hudson Valley, New England's Connecticut villages and New York City. World renowned restaurants are within minutes and recreational activities...
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    Pound Ridge, Westchester County 10576
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, 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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    New City, NY
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Satellite TV
    • Washer
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious open concept loft apartment is 1,850 Sq Ft located in the middle of the city everything you need restaurants, bars, grocery, pharmacy, tours attractions is with in a few blocks…<BR><BR>ITS A FULL 2 BEDROOMS, 1 BATH, THE MASTER HAS A KING MATTRESS 2ND BEDROOM HAS A QUEEN BED TOTALLY...
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    New City, New York 10001
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 8
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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
    • 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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    Fort Montgomery, NY
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Secure Parking
    • Satellite TV
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    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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    Croton on Hudson
    8 Bedrooms, 7 Bathrooms, Sleeps 24 Quick View
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    • Balcony
    • Housekeeping Included
    • Patio
    • DVD Player
    • Washer
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Secluded and Private estate on over 100 protected acres.this historically significant 1895 estate boasts a lot of extras. Tennis court, hiking trails, fishing, golf course 4 miles away, meticulously maintained, each room tastefully decorated, immaculate. Cook's gourmet kitchen includes Viking...
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    Croton on Hudson, Westchester County 10520
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 24
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    Mount Kisco
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
    Suitability
    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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    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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    Orangeburg, NY
    6 Bedrooms, 5 Bathrooms, Sleeps 24 Quick View
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    • Hot Tub
    • DVD Player
    • Mountain Views
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Thank you for visiting my listing. I am new on this site but am successfully listed on many other sites for review references search Rockland County NY. HOUSE RULES: Must leave the house as clean if not cleaner then how was given to you, please be respectful to the house and neighbors (especially...
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    Orangeburg, New York 10962
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 24
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    Tuckahoe
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Parking
    • Wi-Fi
    • Private Garden
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Safe and easy 30 minute commute to grand central terminal 42nd street. Comfortable and quiet apartment within a house that has 2 apartments. Enjoy a walkable village that has bars, cafes, banks and bike paths. Concordia college, Sarah Lawrence college are moments away by car or walking 15- 20 min...
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    Tuckahoe, Westchester County 10707
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Cortlandt Manor
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Porch
    • Grill
    • Mountain Views
    • 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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    New City, NY
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
    • Internet Access
    • Central Heating
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    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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    White Plains
    5 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Central Heating
    • DVD Player
    • Patio
    • Grill
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Its an older home built in 1906 and bought by my grandparents 50 years ago. It has a landscaped front and back yard that is professionally maintained. There is a large driveway that can hold an ADDITIONAL 5+ vehicles. There is a back patio where you can grille and lounge. There is a table and...
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    Location Information
    White Plains, Westchester County 10606
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 4
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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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    Location Information
    New City, New York 10019
    Condo/Apartment - 1 Bathroom, Sleeps 4
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