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Elder Access Holiday Rentals in Southold

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    Travellers to Southold are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    15 Matching Rentals in the Southold AreaView all 32 rentals
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    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES1 / 17
    (2)Excellent
    Southold
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Southold
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Southold
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Secure Parking
    • Grill
    • Private Garden
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large beach front with 5 bedrooms (2 ensuite), 4 living rooms, 3.5 baths This is the perfect home for the extended family vacation, with not only 5 bedrooms, including 2 with ensuite bathrooms but 4 separate sitting/family/den or game rooms plus a pool room! The unique layout offers areas to gather...
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    Southold, North Fork 11971
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Sprawling North Fork, Wine Country Retreat with Hot Tub1 / 17
    (1)Excellent
    Southold
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Patio
    • Terrace
    • Central Heating
    • Hot Tub
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Jay is your guy if you’re looking for a beautiful home roughly 2 hours away from Manhattan for that getaway you need to literally get away from it all. The property is sprawling...
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    About this property
    [New listing here, but we have reviews on the other vacation rental sites] Large, airy, split level, four bedroom home that is perfect for a East End getaway. Located just down the road from beaches and less than a mile from the nearest winery, our home offers a great base from which to explore all...
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    Southold, North Fork 11971
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Parking
    • Patio
    • DVD Player
    • Grill
    • Housekeeping Included
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Peaceful Year-Round Escape in the Middle of Wine Country It's starting to warm up so come to the North Fork - Sip local wine on the front porch or watch the waves at the private beach which is just a short walk away. Relax and kick back in our 3 bedroom house in Long Island's North Fork. Close...
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    Southold, North Fork 11971
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    The following rentals are within 10 kilometres of Southold.
    Cutchogue Beach Cottage1 / 18
    (9)Excellent
    Cutchogue
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Outdoor Dining Area
    • Washer
    • Wi-Fi
    • Grill
    • Patio
    • Central Heating
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 August 2016
    We had a very happy stay here. Contact with Julie was first class, the house is very tastefully decorated and comfortable. It is ideally situated to explore further but has...
    Reviewed 9 August 2016
    We so enjoyed our time here. You really can't find a more homey cottage and the close proximity to the great beach and scenic hilltop playground was tops. Julie was wonderful...
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    About this property
    Cozy Cutchogue Beach Cottage on the North Fork of Long Island. It has 2 bedrooms with queen sized beds and there is a sleeping loft appropriate for children over 9 years old (one queen sized bed and one twin). Deck and backyard with gas grill, outdoor picnic table, fire pit, and tire swing....
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    Cutchogue, North Fork 11935
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    The Farmhouse1 / 15
    (1)Very good
    Greenport
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 February 2017
    My family rented this house for the holiday week between Christmas and New Years. The house is located within walking distance to town - which was quite great The house has...
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    About this property
    Renovated and tastefully furnished, The Farmhouse features one of the largest wrap around porches in the village and it is enviably located steps away from the town's best restaurants and bars, as well as just 3 short blocks to the beach. The space Just steps away from the center of the Greenport...
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    Greenport, North Fork 11944
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Greenport
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built in 1828 for a ship’s captain, this historic property remains as one of the oldest structures in the village. Original details abound. Large, bright & airy rooms. Brand new furnishings. Perfect for entertaining or a quiet weekend retreat. The Space Located on a tree lined street this...
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    Greenport, North Fork 11944
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Greenport
    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Elegant and especially designed and built for one of the wealthiest bankers on the North Fork. Situated on enormous 3/4 acre property in the most prestigious setting of the National Historic District in Greenport Village. Lovingly restored to its original elegance and authentic Classic Queen...
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    Location Information
    Greenport, North Fork 11944
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    Cutchogue
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Patio
    • Private Garden
    • Washer
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly renovated cottage has a spacious living room, large eat-in-kitchen, 2 bedrooms; one with queen-sized bed, the other with two twins, and one full and one half bath. There is a waterview across the street from the relaxing 'pebble lounge' the garden seating area in front of the house....
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    Cutchogue, North Fork 11935
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Greenport
    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will love this 4 bedroom 4.5 bathroom charmer on a quiet street. Walk to town, shops, carousel LIRR Jitney and ferry to Shelter Island Golf course and beaches 1 mile away. There are over 40 wineries nearby. The front deck has 2 Adirondack chairs to just relax. A full deck off the back over...
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    Greenport, North Fork 11944
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Garden
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Designed and built in 2003, this cozy house has water views of Peconic Bay, enormous glass skylights, fully equipped kitchen, two bedroom, two bath, washer, dryer, Wifi, flat screen tv, private rose garden, private parking, a kayak, two bicycles, public swimming dock at end of block, and is one...
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    Greenport, North Fork 11944
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Peconic
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Parking
    • Grill
    • Housekeeping Included
    • Air Conditioning
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enter a world of tranquility and surround yourself with the beauty of nature! Decorated with an eclectic mix of antique and contemporary furniture, the home has three bedrooms, one bath, dining room, living room with large flat screen tv, sunroom with seating and dining area. Kitchen is remodeled...
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    Peconic, North Fork 11958
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Cutchogue
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Grill
    • Cable/satellite TV
    • Washer
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A new Fleets Neck home( May 2017), 2 blocks from Wickham Creek and a 10 minute walk to a lifeguard protected town beach and park. Beach parking permit supplied. Enjoy great restaurants and wineries near by. Sit on the covered front porch and commune with the wildlife while enjoying morning coffee....
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    Location Information
    Cutchogue, North Fork 11935
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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