Holiday Rentals in Town of Southold Town
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Our top choices for Town of Southold Town holiday rentals
1. Cliffside Resort Condominiums
Cliffside Resort CondominiumsGreenport
9.0 out of 10, Wonderful, (300 reviews)
"Great condo. Very nice location and grounds."
William
The price is €299
includes taxes & fees
26 Nov - 27 Nov
2. North Fork Resort
North Fork ResortGreenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
Altynai
The price is €332
includes taxes & fees
19 Nov - 20 Nov
3. Montauk Manor
Montauk ManorMontauk
9.2 out of 10, Wonderful, (1,425 reviews)
"We’ve been to Montauk Manor many times. The inside pool area is updated and nice to use. Gavin a restaurant there is quite convenient. The units are comfortable and lovely with fully stocked kitchens."
barbara
The price is €161
includes taxes & fees
2 Dec - 3 Dec
4. Windward Shores Ocean Resort
Windward Shores Ocean ResortNapeague
8.8 out of 10, Excellent, (333 reviews)
"Omg so peaceful and beautiful. Felt like I was in paradise. My fiancee and I enjoyed every moment except checking out because we did not want to leave. Such beauty it was worth the 3 hour car ride. Perfect getaway.💜🙏"
Banessa
The price is €161
includes taxes & fees
16 Nov - 17 Nov
5. Montauk Oceanside Suites
Montauk Oceanside SuitesDowntown Montauk
8.4 out of 10, Very good, (461 reviews)
"The room was very clean and well taken care of."
Mitchell
The price is €151
includes taxes & fees
16 Nov - 17 Nov
6. The Surf Club
The Surf ClubMontauk
8.6 out of 10, Excellent, (305 reviews)
"Staff are nice"
na
The price is €581
includes taxes & fees
15 Nov - 16 Nov
7. Offshore Spa & Residences
Offshore Spa & ResidencesDowntown Montauk
8.4 out of 10, Very good, (5 reviews)
"What a memorable way to celebrate America’s 250th Anniversary and the Fourth of July at Offshore Montauk. The festive atmosphere, beautiful weather, beach days, and fireworks made for an unforgettable getaway.
The property is beautifully designed with thoughtful room layouts, high-end appliances, and quality finishes that create a luxurious yet comfortable experience. The attention to detail throughout the property is impressive, and it's exciting to see the continued improvements being...
Frank
The price is €326
includes taxes & fees
15 Nov - 16 Nov
8. Groton Home < 1 Mi to Beach on Long Island Sound!
Groton Home < 1 Mi to Beach on Long Island Sound!Groton
The price is €729
includes taxes & fees
22 Nov - 23 Nov
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 Town of Southold Town Hotel Reviews
The Shoals Suites and Slips
10/10 Excellent
Find out more about Town of Southold Town
Holiday Homes in Town of Southold Town
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