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Southold Vacation Rentals(135)

135 Results
$950 - $2,000
per night
2 - 4 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 12
2 - 4 night min stay
(18)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 30 night min stay
(5)
$350 - $485
per night
1 - 3 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
1 - 3 night min stay
(6)
$493 - $2,225
per night
3 - 14 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
3 - 14 night min stay
1 Review
  • 5 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 10
3 - 7 night min stay
(3)
  • 4 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 8
4 - 14 night min stay
2 Reviews
$1,490 - $3,490
per night
2 - 4 night min stay
  • 6 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 18
2 - 4 night min stay
1 Review
  • 6 BR,
  • 3 BA,
  • Sleeps 10
1 - 3 night min stay
(5)
  • 5 BR,
  • 5 BA,
  • Sleeps 10
1 - 30 night min stay
$1,500 - $2,000
per night
3 night min stay
  • 5 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 10
3 night min stay
$305 - $1,400
per night
4 night min stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
4 night min stay
$500 - $600
per night
2 - 7 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
2 - 7 night min stay
  • Studio,
  • 1 BA,
  • Sleeps 3
2 - 5 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 10
2 night min stay
1 Review
$214 - $400
per night
3 - 7 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 - 7 night min stay
1 Review
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night min stay
(3)
$1 - $4,250
per night
1 - 3 night min stay
  • 9 BR,
  • 10 BA,
  • Sleeps 32
1 - 3 night min stay
$200 - $250
per night
1 - 3 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
1 - 3 night min stay
$175 - $225
per night
2 - 3 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 3 night min stay
(7)
$200 - $250
per night
1 - 3 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
1 - 3 night min stay
2 Reviews
$5,000 - $8,000
per week
3 - 7 night min stay
  • 3 BR,
  • 4 BA,
  • Sleeps 10
3 - 7 night min stay
2 Reviews
$4,500 - $7,000
per week
7 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 7
7 night min stay
(6)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
14 night min stay
(7)
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 - 7 night min stay
(5)
$567 - $1,200
per night
4 - 30 night min stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 8
4 - 30 night min stay
(3)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night min stay
1 Review
3 night min stay
  • 5 BR,
  • 3 BA,
  • Sleeps 12
3 night min stay
(3)
$5,000 - $5,833
per week
14 - 31 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
14 - 31 night min stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 7 night min stay
(4)
  • 5 BR,
  • 4 BA,
  • Sleeps 10
4 night min stay
(3)
 

Recent Southold Reviews

Beauty at it's best!

5 of 5
My employer hosted a retreat at this amazing hidden gem! The furnishing and atmosphere was very warm, clean, inviting and very functional for a party of 12. The property manager, Matteo, was very gracious, accommodating and professional. Great sun rises, great sunsets only a short trip away from NYC hustle and bustle. It was relaxation at its best! I highly recommend this home.
  • Submitted: May 18, 2015
  • Stayed: Apr 2015

It was like living in a fairy tale.

5 of 5
Beautiful cottage surrounded by flowers, water and wonderful sunsets.
  • Submitted: May 18, 2015
  • Stayed: Aug 2014

This home is ideal for a large family gathering.

5 of 5
We booked this home for a week in late April in order to bring together a large number of people who had a tie with the North Fork. Everything worked out perfectly: the house is well furnished and we had no difficulty serving 20 people for dinner Saturday night. Maria Trupia, the owner, can best be described in one word: gracious. She was most accommodating and helpful. For anyone contemplating a stay in or around Mattituck, this is the place.
  • Submitted: May 13, 2015
  • Stayed: Apr 2015