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Holiday Rentals and Homes in Sag Harbor, NY

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    Travellers to Sag Harbor are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 10
    5 of 5 stars (3) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    3 of 5 stars (1) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 16
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    5 of 5 stars (4) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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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... View all property information
    Location Information
    Sag Harbor, Hamptons 11963
    4 of 5 stars 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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    1 / 28
    5 of 5 stars (4) Excellent
    5 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    Only for the very discerning renter. It is a designer's own home. Please read rental rates before inquiring. Minimum rental is 2 weeks during High Season unless you see an availability between rentals. During the off season 1 week rentals may be possible. This elegant 6000 square foot home... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 11
    5 of 5 stars (1) Excellent
    Private Room, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
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    About this property
    This whaling captain's house has been in my family six generations. We offer the original wing of house for weekend rental May through October. Each bedroom has a water view, and they share a dressing room/office. Enjoy the spacious porch, that includes an eating area and porch swing. if you... View all property information
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    Sag Harbor, Hamptons 11963
    5 of 5 stars Reviewed yesterday
    This place is beautiful. Amazing views of the water, gorgeous historic house, and probably the most relaxing porch I've ever had the privilege of dozing on. Thank you so much for...
    5 of 5 stars Reviewed 1 week ago
    Ann was the perfect host providing the best breakfast of home made granola and fruit, muffins and bagels rounded off with fresh coffee. The house is a museum that you effectively...
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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,... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 13
    5 of 5 stars (4) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    Forever Cottage is a charming, one-bedroom guest cottage plus newly added separate, modern 'boutique' Studio which rents separately, just steps from Main Street in the scenic village of Sag Harbor, NY, available to rent for weeks, weekends or longer stays- year-round. Sag Harbor is a beautiful,... View all property information
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    Sag Harbor, Hamptons 11963
    5 of 5 stars Reviewed 18 September 2014
    After spending our first night out in the Hamptons at what was described as a luxury hotel which turned out to be a 1960's rehabbed motel we were THRILLED when we got to our...
    5 of 5 stars Reviewed 12 August 2011
    This cottage was charming and centrally located. The owner lives near by and was very sweet and helpful. It rained the whole time we were there, but even so, we had the best...
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    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... View all property information
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    Sag Harbor, Hamptons 11963
    3 Bedrooms, 5 Bathrooms, Sleeps 6 | Quick View
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    About this property
    THE PERFECT HAMPTONS LOCATION, VILLAGE AND BEACHES AUG 2016, RENTALS ARE BY-THE-MONTH ONLY. Simply the best location in the Hamptons, this house is a short walk to the beautiful village of Sag Harbor, but hidden away in a forest of trees, and extremely quiet and private. This unique designer... View all property information
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    Sag Harbor, Hamptons 11963
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    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... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 16
    5 of 5 stars (1) Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    About this property
    GREAT HOUSE FOR A GATHERING OF FRIENDS OR FAMILY POOL WITH DECKING AND LOUNGE CHAIRS KITCHEN WITH GRANITE COUNTER TOPS, 2 LIVING ROOM AREAS, 2 EATING AREAS, GOLD CABLE, WIFI 6 BEDROOMS SHORT DRIVE TO SAG HARBOR/SOUTHAMPTON VILLAGE OR OCEAN BEACHES. Beds: 4 King Beds, 1 Queen Bed, 4 Twin... View all property information
    Location Information
    Sag Harbor, Hamptons 11963
    5 of 5 stars Reviewed 4 October 2014
    Hawk Haven is a wonderful escape, ideal for relaxing away from it all . Wild turkeys and deer gather on the vast lawn in the early evening and it is hard to believe you are right...
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    5 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Beautiful North Haven Minutes from Sag Harbor Village and Ferry to Shelter Island The heart of the Hamptons! Close to Bridgehampton, East Hampton, Southampton, Water Mill, Shelter Island. Walking distance from beaches and town. A park-like 2 acres with a man-made pond is the lush setting for... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 14
    5 of 5 stars (2) Excellent
    Private Room, 2 Bathrooms, Sleeps 7 | Quick View
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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... View all property information
    Location Information
    Sag Harbor, Hamptons 11963
    5 of 5 stars Reviewed 3 weeks ago
    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 you...
    5 of 5 stars Reviewed 11 June 2016
    My family and I (six people) stayed in this lovingly cared for home while attending a wedding. I can truly say that we were delighted with the accomodations and the warm...
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    1 / 12
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
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    Sag Harbor, Hamptons
    7 Bedrooms, 9 Bathrooms, Sleeps 24 | Quick View
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    With 7 bedrooms, 8.5 bathrooms and the ability to sleep 24 guests, this spectacular property provides everything you’ll need for a relaxing stay. Enjoy the private pool and spa, spacious deck, game room and workout room and stunning tennis court! Welcome to your sumptuous home-away-from-home in... View all property information
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    Sag Harbor, Hamptons 11963
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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... View all property information
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    Sag Harbor, Hamptons 11963
    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Walk in to the view of the sky and bay through the living room. The master suite is its own floor. the house is modern, there are three other bedrooms. Perfect home for a summer vacation. A short ride to Main Street, Sag Harbor, short walk to bay beach. View all property information
    Location Information
    Sag Harbor, Hamptons 11963
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Only for the very discerning renter. It is a designer's own home . Minimum rental is 14 nights. Please, please read rental rates before inquiring. Please Do NOT inquire about weekends . No parties whatsoever will be permitted. This elegant 6000 square foot home features vaulted ceilings, first... View all property information
    Location Information
    Sag Harbor, Hamptons 32963
    1 Bedroom, 1 Bathroom, Sleeps 8 | Quick View
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    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... View all property information
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    Sag Harbor, Hamptons 11963
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    *Summer Special: Reduced Summer Rates!*  Escape from reality in this charming 2-bed, 2-bath Sag Harbor house, which sleeps up to 6. Located just minutes from a private beach, restaurants and shopping, this darling abode is the ideal destination for those looking to explore the Hamptons! You’ll... View all property information
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    Sag Harbor, Hamptons 11963
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
    Location Information
    Sag Harbor, Hamptons 11963
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    It's like getting a free house! Generous lot bordering golf course has room for a substantial house, pool and tennis court. Presently improved with an easygoing modern home bordering Noyac Golf Club, with updated kitchen and baths, boasting a free-flowing floor plan, opening onto a large deck... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 22
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This house 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 acres. Pool with spa is included with this home. It... View all property information
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    Sag Harbor, Hamptons 11963
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    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... View all property information
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    Sag Harbor, Hamptons 11963
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Patio
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    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... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 12
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Designer's own home boasts every detail. This stylish home has stainless steel chef's kitchen with wine room, breakfast bar and butler's pantry. Dining room with venetian palster walls and modern crystal chandelier. Living room w fireplace and 50" tv. All marble and travertine baths. Master is en... View all property information
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    Sag Harbor, Hamptons
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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... View all property information
    Location Information
    Sag Harbor, Hamptons 11963
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Charming & Private Sag Harbor Home - sleeps 10-12 with Pool and fireplaces Traditional home on 1/2+ acre lot with mature landscaping. Main house includes 5 bed/3 bath/ 2 fireplaces and central AC. Large deck overlooking pool and private backyard (reserve on 2 sides). Separate guest cottage with... View all property information
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    Sag Harbor, Hamptons 11963
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    A beautiful custom built 2 bedroom home offers authentic charm and elegance from the finishing to the furnishings. It is located in a waterfront community just steps to the Peconic Bay with access to launching your boat! Enjoy the view of the heated pool from a spacious deck overlooking a large... View all property information
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    Sag Harbor, Hamptons 11963
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    PHEASANT ESCAPE GUEST SUITE An Accommodation for Particular People. Escape to Nature Without Roughing It. INFANTS and CHILDREN ALWAYS WELCOME. Special Promotion Option A: Stay 2 weekdays and get 25% off the 2nd weeknight. Special Promotion Option B: Stay 3 weekdays and get 50% off the 3rd... View all property information
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    Sag Harbor, Hamptons 11932
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Minutes from Sag Harbor Village, beaches, and steps to Sag Harbor Cove. This charming 3 bedroom cottage is situated on a quiet dead end street.. Living room with fireplace, family room with hand hewn beams, sunny eat-in-kitchen, wide pine flooring,and CAC. This half acre property has a heated... View all property information
    Location Information
    Sag Harbor, Hamptons 11963