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Southold Waterfront Vacation Rentals Vacation Rentals(27)

27 Results
$400 - $450
per night
1 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
1 - 3 night minimum stay
(6)
$550 - $750
per night
2 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(17)
$300 - $450
per night
2 - 3 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 5
2 - 3 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 - 7 night minimum stay
(4)
$450
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 5 night minimum stay
(4)
$225 - $300
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(9)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
5 - 7 night minimum stay
1 Review
$190 - $275
per night
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 3 night minimum stay
(9)
$200 - $225
per night
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 3 night minimum stay
(40)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
5 - 7 night minimum stay
(3)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
(4)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 - 7 night minimum stay
(6)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
14 - 31 night minimum stay
  • 5 BR,
  • 2 BA,
  • Sleeps 6
$300 - $1,250
per night
2 - 3 night minimum stay
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
2 - 3 night minimum stay
(73)
$500
per night
3 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
10 more choices from the HomeAway Network
$500 - $600
per night
2 - 14 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
2 - 14 night minimum stay
$429 - $571
per night
2 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 10
2 - 7 night minimum stay
(27)
$350
per night
2 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
$429 - $857
per night
3 - 30 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
3 - 30 night minimum stay
(8)
$300
per night
2 - 6 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
2 - 6 night minimum stay
(4)
$429 - $1,000
per night
4 - 11 night minimum stay
  • 4 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 14
4 - 11 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
5 night minimum stay
(3)
  • 6 BR,
  • 5 BA,
  • Sleeps 12
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 - 30 night minimum stay
1 Review
$300
per night
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 night minimum stay
(10)
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Recent Southold Reviews

highly recommend this property, great location

5 of 5
This house is beautiful with amazing views, house sits right on the Long Island sound and you have your own private beach, the sunsets are gorgeous every night. The customer service is outstanding and very helpful giving us ideas of places to go. There are lots of places to check out right near the house, wineries, farms, Greenport village, orient point, etc. Our overall experience was fantastic and I highly recommend this beach house and I will definitely be making another trip to this location.
  • Submitted: Oct 4, 2014
  • Stayed: Sep 2014

A wonderful getaway!

5 of 5
We had a wonderful time at this cabin! The cabin is absolutely lovely and well cared for. We were four adults and a toddler and felt very comfortable. The outside space was so private and having such a huge yard with its own water access really made it feel like a retreat. The hosts were very communicative and extremely helpful with all logistics and providing tips for activities around the area. We would certainly stay there again!
  • Submitted: Oct 2, 2014
  • Stayed: Sep 2014

Wonderful cottage - perfect location!

5 of 5
My husband and I enjoyed our week long stay at the cottage. Comfortable and cozy with easy access to wineries, restaurants and the beach! Added bonus of the hot tub and lake make it a perfect get away.
  • Submitted: Sep 4, 2014
  • Stayed: Jul 2014