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

Town of Southold Town Vacation Rentals

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Our top choices for Town of Southold Town vacation rentals

A modern house with a deck, outdoor seating, and a fire pit.

1. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (61 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is P16,692
P19,070 total
includes taxes & fees
Oct 4 - Oct 5
North Fork Resort
Terrace/patio

2. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (295 reviews)
"Great place!"
United States
Christine
The price is P10,591
P19,051 total
includes taxes & fees
Nov 1 - Nov 2
Cliffside Resort Condominiums
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, (1,409 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is P8,083
P10,461 total
includes taxes & fees
Oct 12 - Oct 13
Montauk Manor
Room

4. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (324 reviews)
"Easy access to the beach. Perfect weather. Nicely furnished and updated rooms and bathrooms. The gym is tiny- not much equipment. The location is perfect for Montauk and Amagansett. The staff were very nice and hard working."
United States
Gaurang J
The price is P7,453
P10,219 total
includes taxes & fees
Oct 12 - Oct 13
Windward Shores Ocean Resort
Room

5. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (252 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
The price is P7,349
P10,437 total
includes taxes & fees
Oct 5 - Oct 6
Driftwood Resort
Room

6. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (453 reviews)
"The room was very clean and spacious."
United States
Jadana
The price is P7,392
P9,127 total
includes taxes & fees
Oct 20 - Oct 21
Montauk Oceanside Suites
Living area

7. The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (302 reviews)
"Found mold under the pull-out couch"
United States
Anna
The price is P12,923
P18,688 total
includes taxes & fees
Oct 31 - Nov 1
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

Zey Hotel

Zey Hotel

10/10 Excellent
"Had a great stay here. James was very welcoming and a great host. The town is great with nice shops and restaurants."
Michael 1-night trip
Posted 1 hour ago
Zey Hotel

Find out more about Town of Southold Town

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