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Our top choices for Southold vacation homes
1. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + OfficePipes Cove
10.0 out of 10, 31, (31 reviews)
"We had a wonderful time at this location. It meant all of our expectations and was perfectly advertised. We love how close it was to downtown Greenport."
Michael M.
The price is AED 645
AED 1,563 total
includes taxes & fees
16 Sep - 17 Sep
2. Beach Block Hideaway
Beach Block HideawayPipes Cove
10.0 out of 10, 10, (10 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
Teresa C.
The price is AED 716
AED 1,536 total
includes taxes & fees
16 Sep - 17 Sep
3. Aqua Vista
Aqua VistaPipes Cove
10.0 out of 10, 45, (45 reviews)
"Great location and nice spot."
Kerri L.
4. The SandPiper
The SandPiperPipes Cove
9.6 out of 10, 52, (52 reviews)
"Very wonderful location so close to the train station will come back soon"
Julian V.
5. American Beech in Greenport - Petite King Room 7
American Beech in Greenport - Petite King Room 7Greenport
9.4 out of 10, 6, (6 reviews)
"Great place! So nice."
Paul F.
The price is AED 841
AED 1,209 total
includes taxes & fees
30 Sep - 1 Oct
6. BlackBerry Private home with jacuzzi yearlong
BlackBerry Private home with jacuzzi yearlongEast Hampton
9.2 out of 10, 7, (7 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
Suzanne R.
The price is AED 323
AED 4,741 total
includes taxes & fees
16 Sep - 17 Sep
7. Renovated Townhouse walk to all
Renovated Townhouse walk to allGreenport
9.6 out of 10, 14, (14 reviews)
"We had a wonderful girls weekend in Greenport. The house was perfect for the three of us. Loved the location. We didn’t get to use the back area due to the weather, but it looked so inviting. Next time!"
Melissa A.
The price is AED 1,339
AED 2,612 total
includes taxes & fees
17 Sep - 18 Sep
8. Adorable Cottage, 5 min walk to water & town
Adorable Cottage, 5 min walk to water & townWestbrook Center
9.2 out of 10, 17, (17 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
Donovan V.
The price is AED 608
AED 1,732 total
includes taxes & fees
16 Sep - 17 Sep
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Southold Hotel Reviews
Greenview Inn Riverhead
10/10 Excellent
