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Holiday Homes in Chappaqua

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    All 34 Rentals in Chappaqua
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    Chappaqua
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    The following rentals are within 25 kilometres of Chappaqua.
    Castle By The Lake1 / 15
    (2)Excellent
    Putnam Valley, NY
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Relaxing Modern Retreat1 / 18
    (8)Very good
    Lake Peekskill, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Putnam Valley, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Terrace
    • DVD Player
    • Secure Parking
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lakefront paradise has waterfront views that will leave you breathless. It is rated five star by Baron Realty and Fulline Home Research. The property is located one hour north of Manhattan off the Taconic Parkway or 15 min. east of the Garrison, New York Metro North train station on the...
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    Putnam Valley, New York 10579
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 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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    Greenwich, CT
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Rye
    5 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Internet Access
    • Cable/satellite TV
    • Private Garden
    • Patio
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great for families or temporary corporate accommodation. This 3,000 sq. ft property is only 35 minutes to NYC by Metro-North and 5 walking distance to Rye downtown and the train station. Your family will enjoy from 'Rye Country Club' with swimming pools, tennis, and golf. You can also visit the...
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    Rye, Westchester County 10580
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 8
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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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    Nyack, New York 10994
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    NYC Midtown 30 minutes-Scarsdale on Golf Course1 / 23
    (5)Excellent
    Scarsdale
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Balcony
    • Patio
    • DVD Player
    • Grill
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 November 2017
    My extended family gathered here from all corners of the country to be under one roof together- this home made it all possible. Quick access from train or Bronx River Parkway...
    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...
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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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    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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    Greenwich, CT
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Washer
    • Cable/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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    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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    Mount Kisco
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Washer
    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 provide 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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    North Salem
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Balcony
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This gracious and well appointed Coach House has been beautifully renovated. The Light and Airy Two Floor cottage is situated on the property of an historic home, and offers a Pool, mature gardens, riding and hiking trails. It's near excellent fishing spots. Dine al fresco on your private patio!...
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    North Salem, Westchester County 10560
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Serene Connecticut Retreat - Luxury 2 bedroom apt1 / 21
    (2)Very good
    Stamford, CT
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Patio
    • Washer
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 August 2015
    The apartment was in a lovely setting, attached to the family house, but totally private. Liz the landlord was very friendly, helpful and knowledgeable of the area. The...
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    About this property
    Completely updated apartment in lovely rural setting but close to everything. Get away without going very far. Take a break from sterile hotel rooms while on business. Private entrance, 2 bedroom, 1.5 bath, fully equipped kitchen, dining room, living room, french doors to patio, balcony off...
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    Stamford, Connecticut 06903
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Irvington
    12 Bedrooms, 9 Bathrooms, Sleeps 30 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Voted one of the most luxurious homes in Westchester County, NY. Located 30 minutes from Midtown Manhattan, this gorgeous historical estate overlooks the Hudson River. Villa Nuits boasts 15,000sq feet of living space. Can sleep up to 26+ guests. All new amenities including fastest wi-fi, high-end...
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    Irvington, Westchester County 10533
    Holiday Rental House - 12 Bedrooms, 9 Bathrooms, Sleeps 30
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    Quaint and immaculate 3 br duplex!1 / 26
    (2)Very good
    Greenwich, CT
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2017
    From opening the front door, we felt at home.It was so inviting, well equipped and we found out with in days that we need a Fridge Freezer with an ice dispenser/cold water in...
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    About this property
    Minutes from Byram beach and also from the main streets of Port Chester, Rye and Greenwich, this fully renovated home boasts hard wood floors, washer dryer, central heating and air conditioning and a wonderful state of the art kitchen with granite counter tops. The property has 3 quaint bedrooms...
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    Greenwich, Connecticut 06830
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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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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    Greenwich, CT
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Private Garden
    • Secure Parking
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Greenwich, Connecticut 06831
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Lakewood Estate; Private & tranquil- less than one hour to NYC, sleeps up to 241 / 11
    (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 29 November 2017
    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 29 November 2017
    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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    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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    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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    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
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Large one bedroom with cozy back yard can sleep 6 people. Beautiful cozy furniture. Very nice and quite neighborhood with lots of convenient stores, bars, and restaurants. Just 8 short block from subway. We expect you to enjoy your stay with us to the fullest, making sure that you'll be provided...
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    New City, New York 10009
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Stamford, CT
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The fabulous apartments at The Blvd offer resident spectacular features like fully-equipped kitchens, spacious closets, hardwood flooring and much more. A furnished sky terrace with outdoor grills & fire pits, a lounge & screening room and a 24 hour fitness center are some of the fantastic...
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    Stamford, Connecticut 06901
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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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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    Orangeburg, NY
    6 Bedrooms, 5 Bathrooms, Sleeps 24 Quick View
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    • Hot Tub
    • DVD Player
    • Mountain Views
    • Cable/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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    White Plains
    3 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Secure Parking
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely Victorian in White Plains AVAILABLE FOR JULY +- a week or so We are on a hill, facing WEST so we get some fantastic sunsets. Close to Manhattan, White Plains is a small city, and a unique suburban community. This wonderful Victorian style house was built in 1902. We have lived here for 35...
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    Location Information
    White Plains, Westchester County 10606
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 4
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    Stamford, CT
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The fabulous apartments at The Blvd offer resident spectacular features like fully-equipped kitchens, spacious closets, hardwood flooring and much more. A furnished sky terrace with outdoor grills & fire pits, a lounge & screening room and a 24 hour fitness center are some of the fantastic...
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    Stamford, Connecticut 06901
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    New City, NY
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Both bedrooms have King size beds with Tempurpedic memory foam cloud mattresses. Kitchen had great counter space, easy for cooking meals in. Living room has cozy Sofa bed with queen size mattress, flat screen TV and is a great lounging and relaxing area. There is cable and Wifi in apartment. Full...
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    New City, New York 10018
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Stamford, CT
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Country Cottage, Kitchen has a stove, microwave, Refig, Double Sink. Living Room, Bedroom, Stiral Staircase to bedrooms, Outside deck, Horses and dogs on property. 7 miles to train station, New York City. 5 Miles to Stamford night life. Walking trails, trout fishing.Very peaceful...
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    Location Information
    Stamford, Connecticut 06903
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    Greenwich, CT
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Washer
    • Parking
    • Wi-Fi
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 July 2016
    We stayed in Greenwich for a week to attended a family wedding. We needed a rental that was big enough for 3 adults with lots of luggage with reasonable access to NY. This...
    Reviewed 7 January 2015
    I stayed here with my family for 5 days in new year's eve, because we wanted to be near Manhattan but in a quiet, nice and safe location. It was exactly what we needed! Very...
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    About this property
    Minutes from Byram beach and also from the main streets of Port Chester, Rye and Greenwich, this fully renovated home boasts hard wood floors, washer dryer, central heating and air conditioning and a wonderful state of the art kitchen with granite counter tops. The property has 3 quaint bedrooms...
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    Location Information
    Greenwich, Connecticut 06830
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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