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

Condo | Terrace/patio

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (285 reviews)
"Great place!"
United States
Christine
The price is ₩433,892
₩621,936 total
includes taxes & fees
Sep 7 - Sep 8
Cliffside Resort Condominiums
Flat-screen TV

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (48 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is ₩454,858
₩519,675 total
includes taxes & fees
Sep 7 - Sep 8
North Fork Resort
Lobby

3. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,388 reviews)
"Property and room very clean Friendly staff and plenty of parking"
United States
Amelia
The price is ₩420,457
₩508,088 total
includes taxes & fees
Sep 7 - Sep 8
Montauk Manor
Apartment | WiFi (free), individually decorated, individually furnished, bed sheets

4. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (247 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
The price is ₩331,538
₩424,916 total
includes taxes & fees
Sep 13 - Sep 14
Driftwood Resort
Iron/ironing board, WiFi (free), individually decorated

5. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (322 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 ₩341,972
₩429,206 total
includes taxes & fees
Sep 14 - Sep 15
Windward Shores Ocean Resort
Apartment | Living area

6. The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (293 reviews)
"Found mold under the pull-out couch"
United States
Anna
The price is ₩466,693
₩628,831 total
includes taxes & fees
Sep 9 - Sep 10
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

Sound View Greenport

Sound View Greenport

10/10 Excellent
"Hotel very well situated with a nice beach and a great pool. The rooms were clean and spacious. There were a lot of families so we couldn’t just sit and enjoy the view with toddlers running around - but that was me 20 years ago. I would recommend but next time I would want to book the private patio rooms. Continental breakfast was great - all around fantastic stay."
Karen 2-night trip
Posted 1 hour ago
Sound View Greenport

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