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Sag Harbor Holiday Rentals

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    Travellers to Sag Harbor are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    All 32 Rentals in Sag Harbor
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    Elegant Designer Hamptons Retreat in Sag Harbor1 / 28
    (5)Excellent
    5 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Sag Harbor with water views & perfect sunsets1 / 11
    (8)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Grill
    • Central Heating
    • Satellite TV
    • Internet Access
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This vacation rental cottage in the Sag Harbor area of the Hamptons is a cozy getaway with 3-bedrooms and 2-bathrooms, comfortably accommodating up to 6 guests. Newly renovated throughout, the property upholds the historic beach cottage charm of the Hamptons! Close to North and South Hampton with...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Internet Access
    • Washer
    • Satellite TV
    • Grill
    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is perfectly located a few blocks from Wollfer Vineyard and blocks away from the town of Sag Harbor. You will have all the privacy you want. Enjoy a beautiful built in pool. The home is clean, stylishly decorated, and close to gorgeous beaches. Work out room, everything! The location...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Satellite TV
    • Grill
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is nestled in a park like setting with a private tree-lined yard. You will have all the privacy you want. Enjoy a beautiful built in pool & Jacuzzi. The home is clean, stylishly decorated, and steps away from a gorgeous north Sea bay beach. Visit Southampton or Sag Harbor town only 3 min...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Satellite TV
    • Wi-Fi
    • Grill
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On a quiet shy 2 acre beautiful parcel adjacent to hundreds of acres of town reserve sits this updated light filled home with sweeping lawn, and reserves on 3 sides for complete privacy. Spacious with 4 bedrooms and 3.5 baths,Two masters with king beds and private baths, two additional bedrooms one...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    Main Street Historic Gingerbread House Full floor1 / 21
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Parking
    • Balcony
    • Terrace
    • Private Garden
    • Air Conditioning
    • Washer
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 October 2015
    The gingerbread house was well located; at the end of the main street of Sag Harbor. It was small but very pretty and although the stairs are a challenge especially with luggage...
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    About this property
    From its commanding position on Main Street in the heart of Sag Harbor village, this spectacular vintage Victorian is an authentic testament to the history of Sag Harbor. With distinctive architecture and classic styling, the impressive house features the Upstairs Apartment with 2 bedrooms, 1...
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    Sag Harbor, Hamptons 11963
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Sag Harbor with perfect water view and sunset1 / 14
    (3)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Outdoor Dining Area
    • Ocean Views
    • Secure Parking
    • Air Conditioning
    • Waterfront
    • Porch
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2017
    My family have just spent 7 days at a charming whaling cottage in Sag Harbor.The position to town was great and the tranquility of the home was ideal.The owners Anne and Dave...
    Reviewed 7 July 2016
    Ann and Dave offer this lovely, historic home to guests and provide everything needed for a wonderful stay. The porch overlooking the water is heavenly. You really feel like...
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    About this property
    Historic whaling captains home. We are the sixth generation to live here. It is a quick walk from our house to the village of Sag Harbor, where you will find restaurants, boutiques, antique stores, marinas and much more. If you wish to stay around the house, we have a dock, hammock and the best...
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    Sag Harbor, Hamptons 11963
    Private Room - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Secure Parking
    • Satellite TV
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a newly renovated bungalow with 2 bedrooms, full living room, eat-in kitchen, closed in and sunny porch, roomie deck with outdoor furniture (in season). It is a 5-10 minute walk to the village, fine restaurants, museums, shops, churches and temple and beach.This is a prime location. The...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Beech Tree Cottage1 / 10
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Satellite TV
    • Shared Garden
    • Wi-Fi
    • Outdoor Dining Area
    • Parking
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2016
    Spent two nights at Beech Tree with my husband and grown son. Cottage is located within walking distance of town, in a nice residential neighborhood. Kitchen is well stocked, we...
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    About this property
    Beech Tree Cottage is a charming two-bedroom, one-bath guest cottage conveniently located in the historic district of Sag Harbor, NY - a 5-minute walk along the waterfront to Main Street and the center of the village. The beach is a short drive or bike ride away. The owners are full-time residents...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Chic and Modern Beach retreat with heated Pool1 / 16
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Parking
    • Private Outdoor Pool (Heated)
    • Washer
    • Wi-Fi
    • Balcony
    • Grill
    • Air Conditioning
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 July 2016
    This house has everything you need and is perfectly located. It is not far from Sag Harbour in a quiet area. Close to marina for kayaking and stand up paddle boarding. With...
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    About this property
    Privately situated on a park-like landscaped grounds, this classic 2 story French cottage was completely renovated for modern comfort and indoor/outdoor summer entertainment. This delightful house features an open-plan living room with fireplace, dining room, a gourmet kitchen with stainless...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Hot Tub
    • Satellite TV
    • Washer
    • DVD Player
    • Waterfront
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Resort style living in this fantastic private beachfront oasis in Sag Harbor Village. Enjoy fabulous views and amazing sunsets over Sag Harbor Bay from this wonderful 3 bedroom, 2.5 bath house with hot tub and sandy beach right in your backyard. Great family rental. Kids have their own private...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Cottage in the historic district1 / 11
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 2017
    Great location. Very convenient to town, beaches and attractions. Claudie and Andrew were great hosts
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    About this property
    Perfect get away in the heart of the village. Newly renovated carriage house in the historic district. 2 bedrooms, kitchen, dining room, living room, full bathroom, private yard. Located in the Historic District of Sag Harbor Village. Only 10 minutes walk to the center and 15 minutes to the...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Grill
    • Private Outdoor Pool (Heated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On a quiet shy acre beautiful parcel sits this updated light filled home in a Development with wide street for walking. With 4 Master Ensuite bedrooms, spacious with 2 masters with king beds and private baths, one with queen bed and private baths and the other with two twin beds and private bath...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Satellite TV
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Put up your feet and relax in this idyllic home just minutes from Long Beach and the rest of the luxuries the Hamptons have to offer. The open concept kitchen is a chef's dream, with a six burner Viking stove, Subzero refrigerator, Bosch dishwasher, and plenty counter space; perfect for...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Housekeeping Included
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautifully renovated 3 BR, 2 Bath home is situated on a quiet street, with a fenced half acre yard. It is located less than a mile to the shops, bars and restaurants of Main Street and the Hampton Jitney stop with service to NYC. The open floor plan boasts an abundance of natural light with 4...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sag Harbor designer home, Chef's kitchen & one block from the water1 / 14
    (2)Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Secure Parking
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    We loved everything about this place. From the outdoor fire pit to my elderly parents having the time of their lives. Everything was impeccable. We look forward to returning...
    Reviewed 23 March 2017
    Our family enjoyed a great week in Sag Harbor and wonderful accommodations. The house is as advertised, nicely and warmly decorated with beautiful pool and outdoor grounds. The...
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    About this property
    For a truly authentic experience of Sag Harbor, stay at this delightful 5-bedroom, 2-bathroom designer's home with oversized heated pool and ideally situated just 2 blocks from Long Beach . With 2,800-square feet of living space and enough sleeping accommodations for up to 10 guests, this residence...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning, spacious three bedroom home, with water views from every room, and a heated gunite pool, will be your dream-come-true vacation rental. You will be minutes away from several gorgeous beaches as well as 1 mile from the lively and historic village of Sag Harbor. Decorated to a high...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
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    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Spacious Contemporary home is great for entertaining and play. The interior kitchen/dining is open and light filled. There are 2 living rooms and 2 dining areas as well as a breakfast bar. There are sliding glass doors to the large deck which affords flow between interior and exterior....
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 20
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    1 Bedroom, 1 Bathroom, Sleeps 8 Quick View
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    • Air Conditioning
    • Outdoor Dining Area
    • Washer
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    • Private Outdoor Pool (Unheated)
    • Shared Garden
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the quaint historic whaling Village of Sag Harbor, 12 minute walking distance to the center of town, with close proximity to the bay and ocean beaches. This European designer's home totals 5000 sq.ft., the lower level just shy of 1000, sq ft and is the designer's private lower level...
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    Sag Harbor, Hamptons 11963
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
    • Hot Tub
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This villa features 5,600 +/- sq. ft. of living space with five bedrooms, four and one-half baths, plus a gourmet kitchen, living room with fireplace, media room, office, large master, and a finished lower level, on 1.87 +/- beautifully landscaped ac. Located in The Hamptons neighborhood in Sag...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Washer
    • Grill
    • Patio
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The feeling of Zen surrounds you as you enter upon this European designer's hideaway..Custom appointments of quality and luxury fill this Hampton's home. Located 12 minutes walk to Main Street of the prestigious Sag Harbor Village....0.4 acres of beautifully manicured totally private lawns with...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    10 Bedrooms, 13 Bathrooms, Sleeps 16 Quick View
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    • Hot Tub
    • Satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • DVD Player
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spectacular 13,000 square foot estate, on 30 acres of open reserve with water views, boasts 11 bedrooms, 13 full bathroom, heated gunite pool, large outside patio area, Grill, perfect for entertaining, weddings, large family gatherings, etc. Located in Bridgehampton neighborhood in Sag Harbor....
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 10 Bedrooms, 13 Bathrooms, Sleeps 16
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Patio
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property has just gone through a hi-end renovation. It has a beautiful updated Viking kitchen, amazing yard with a 50 ft gunite pool with shallow end "tanning bed", great for kids and adults alike! There are four bedrooms, 3 full baths in the main house, plus an additional full bath in the...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Central Heating
    • Patio
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home sits on 2.2 private and gated acres surrounded by nature. Viking kitchen, double sinks, double dishwashers and wine cooler. Six well appointed bedrooms, 3 en-suite. Three fireplaces. Formal living room, den, outdoor den, outdoor living room, formal dining room, covered porch with dining...
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    Sag Harbor, Hamptons 11937
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Washer
    • Hot Tub
    • Ocean Views
    • Balcony
    • Grill
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hello, This is a wonderful beach house to stay over the summer. It has everything you want in it (Salt Water Pool, Wreck Room, Jacuzzi, Home Theater, Alarm Systems, etc...)! For those who want the best, come here. It has wonderful views of beaches. In under 100 yards, you can be at the best...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Village traditional on a quiet village street perfect for family gatherings. Magnificent backyard including a stone patio with fridge, grill, heated gunite pool and beautiful gardens. The park is accessible from our backyard allowing children to enjoy fields and playground and adults to have...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Grill
    • Ocean Views
    • Waterfront
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    • Air Conditioning
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wonderful Sag Harbor VillageWaterfront Cottage for Rent 3 bedrooms, 4 queen size beds , 1 1/2 baths, A/C, Screaming Water views, multi level Decks, Private Sand beach, with Kayaks and fire pit. All inclusive utilities, Maid service (weekly) and wonderful clear Water and sandybeach. Grill,...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    OPEN HOUSE!! Sunday May 18 One of the last houses in the area with pool AND tennis! MD-LD $60,000 Please call first. Welcome to my paradise! My home has everything you need for a fantastic summer. 6 bedroom/4 bath contemporary home on 10 secluded acres. Heated in ground 20x40 pool, all weather...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Grill
    • Air Conditioning
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Sea Breeze House is located in the enchanting community of Sag Harbor. The house is located just steps from the only private beach in the Hampton. You can walk or bike to town. Watch the sunset from the front porch, enjoy the evening sea breeze. The Sea Breeze House is a chic, modern, yet...
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    Sag Harbor, Hamptons
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    NEW CENTRAL AIR CONDITION WITH NEST THAT KEEPS HOUSE KOOL AT ALL TIME .PRICELESS!! All room have the own TV's. All Beds are memory form and super comfortable .house is very clean wit all new linens. 2 ned bathrooms.great home feeling in a family neighborhood. you can walk or walk into town main st...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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