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Compare 1576 Vacation Homes in Southold with updated reviews, rates, and availability.

WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
10.0 out of 10, Exceptional, (168)

Large Charming Historic House close to Beaches
Large Charming Historic House close to Beaches
9.6 out of 10, Exceptional, (23)

Waterfront House with picture-perfect views from all 3 levels.
Waterfront House with picture-perfect views from all 3 levels.
9.6 out of 10, Exceptional, (79)

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
9.0 out of 10, Wonderful, (88)

Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi
Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi
7.4 out of 10, Good, (3)

Charming Village home in the heart of Southampton
Charming Village home in the heart of Southampton
10.0 out of 10, Exceptional, (20)

Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
9.6 out of 10, Exceptional, (12)

10 Bedroom Hampton House with a regulation size Pickleball
10 Bedroom Hampton House with a regulation size Pickleball
10.0 out of 10, Exceptional, (25)
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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Other property types in Southold

North Fork 7 Bedroom Farmhouse Escape
North Fork 7 Bedroom Farmhouse Escape
9.4 out of 10, Exceptional, (3)

Windward Shores Ocean Resort
Windward Shores Ocean Resort
8.8 out of 10, Excellent, (275)
The price is SAR 494
SAR 646 total
includes taxes & fees
18 Mar - 19 Mar

Cliffside Resort Condominiums
Cliffside Resort Condominiums
9.0 out of 10, Wonderful, (207)
The price is SAR 650
SAR 905 total
includes taxes & fees
26 Mar - 27 Mar
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.
Recent reviews of Southold hotels
Recent reviews of Southold hotels

Water's Edge Resort & Spa
5/5 Excellent
"Lovely property .... The dinner was great . Room service was very convenient and fast . The spa was wonderful Justine was amazing with the massage I felt so relaxed after. Our pedicures the next day were equally amazing, my feet are so soft and clean my polish is neat. I will definitely be back for a massage and relaxing overnight trip . "
A verified traveler stayed at Water's Edge Resort & Spa
Posted 1 day ago
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