A white colonial-style house with a green roof and a lighthouse tower.

Vacation Rentals in Town of Southold Town

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Our top choices for Town of Southold Town vacation rentals

A balcony with a view of the sea, a dining table, and a blue house in the background.

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is NT$5,510
NT$9,912 total
includes taxes & fees
Nov 12 - Nov 13
Cliffside Resort Condominiums
A modern house with a deck, outdoor seating, and a fire pit.

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (70 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is NT$10,475
NT$11,967 total
includes taxes & fees
Oct 26 - Oct 27
North Fork Resort
A spacious hallway with high ceilings, arched columns, and chandeliers.

3. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,418 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is NT$4,765
NT$6,082 total
includes taxes & fees
Nov 17 - Nov 18
Montauk Manor
Room

4. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (331 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.💜🙏"
United States
Banessa
The price is NT$4,474
NT$5,998 total
includes taxes & fees
Nov 1 - Nov 2
Windward Shores Ocean Resort
Property grounds

5. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
8.8 out of 10, Excellent, (256 reviews)
"Great right on the beach property with nice pool."
United States
Julian
The price is NT$4,043
NT$5,680 total
includes taxes & fees
Oct 30 - Oct 31
Driftwood Resort
Room

6. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (457 reviews)
"The room was very clean and spacious."
United States
Jadana
The price is NT$4,621
NT$5,634 total
includes taxes & fees
Oct 26 - Oct 27
Montauk Oceanside Suites
Living area

7. The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (305 reviews)
"Staff are nice"
United States
na
The price is NT$7,127
NT$10,200 total
includes taxes & fees
Nov 4 - Nov 5
The Surf Club
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

The Shoals Suites and Slips

10/10 Excellent
"Wonderful stay. Everything was perfect. Front desk people were lovely"
David 1-night trip
Posted less than an hour ago
The Shoals Suites and Slips

Find out more about Town of Southold Town

Vacation Apartments in Town of Southold Town

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