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Sag Harbor Holiday Homes

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    Travellers to Sag Harbor are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 11
    5 of 5 bubbles (3) Excellent
    Private Room, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 28
    5 of 5 bubbles (4) Excellent
    5 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    1 / 21
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    5 of 5 bubbles (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 bubbles Reviewed 8 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 you...
    5 of 5 bubbles Reviewed 12 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 / 11
    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
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    Sag Harbor, Hamptons 11963
    1 / 10
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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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... View all property information
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    Sag Harbor, Hamptons 11963
    4 of 5 bubbles 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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    1 / 14
    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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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... View all property information
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    Sag Harbor, Hamptons 11963
    5 of 5 bubbles 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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    1 / 16
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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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... View all property information
    Location Information
    Sag Harbor, Hamptons 11963
    5 of 5 bubbles Reviewed 5 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 shops...
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    1 / 29
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    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... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 8
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    GREAT HOUSE FOR A FEW FRIENDS OR FAMILY AMAZING DECKING, SPORT AREA, HAMMOCK AND LOUNGE CHAIRS. HOT TUB OFF LOWER DECK KITCHEN WITH STONE COUNTER TOPS, OPEN LIVING ROOM AREA, DINING AREA, HOT TUB, GOLD CABLE, WIFI 3 BEDROOMS UP, SUITE DOWNSTAIRS SHORT DRIVE TO SOUTHAMPTON VILLAGE OR... View all property information
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    Sag Harbor, Hamptons 11963
    5 of 5 bubbles 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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    1 / 27
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    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. 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 away.... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 17
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 26
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    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... View all property information
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    Sag Harbor, Hamptons 11937
    1 / 30
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    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 / 8
    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
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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 know you made the right choice upon arrival... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 17
    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 / 36
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    5 bedrooms, 4.5 full baths. New construction, steps to private beach. Bathrooms of Carrara marble and polished chrome finishes. Open living/dinning and family room with 2 fireplaces. Mahogany deck and beautiful 20x40 Gunite heated pool with Danish brick patio. Gourmet country kitchen with... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 7
    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
    1 / 18
    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
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    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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 / 17
    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
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    Sag Harbor, Hamptons 11963
    1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 17
    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
    1 / 12
    3 of 5 bubbles (1) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | 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 Space: The Sea Breeze House is a chic,... View all property information
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    Sag Harbor, Hamptons 11963
    3 of 5 bubbles Reviewed 11 July 2016
    Caretaker was difficult to get hold of. Had to make many phone calls and e mails and to complain TripAdvisor. First time renting house made my experience unpleasant.
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    1 / 5
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This beach vibes cottage is located in Sag Harbor village, you can walk to town, bike or walk to the beach. The house is located in the only private beach community in Sag Harbor. The cottage comes fully furnished with everything you need to have a memorable stay in Sag Harbor. No smoking Not... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 10
    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
    1 / 8
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    The Sea Breeze House is located in the enchanting community of Sag Harbor. The house is located walking distance to the only private beach in the Hamptons. You can walk or bike to town. Grab a bottle of wine head to the beach and enjoy the amazing sunset on the east end, sit on the porch relax and... View all property information
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    Sag Harbor, Hamptons 11963
    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
    1 / 28
    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
    1 / 16
    10 Bedrooms, 13 Bathrooms, Sleeps 16 | Quick View
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    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.... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 18
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 24
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    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... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 7
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 39
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Child-friendly
    • Smoking allowed
    • x
    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
    Location Information
    Sag Harbor, Hamptons 11963
    1 / 5
    5 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Outdoor...
    • Private Garden
    • Satellite TV
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Sag Harbor, Hamptons 11963
    1 / 9
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Amenities & Details
    • Private Garden
    • Parking
    • Grill
    • DVD Player
    • Private Outdoor...
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    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