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

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (275 reviews)
"Comfortable and clean, and the beach location is amazing. The sunset was spectacular. We will definitely come back again!"
United States
Suzanne
The price is NT$16,098
NT$19,799 total
includes taxes & fees
Aug 12 - Aug 13
Cliffside Resort Condominiums
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (39 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is NT$17,104
NT$19,542 total
includes taxes & fees
Aug 10 - Aug 11
North Fork Resort
Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,371 reviews)
"Property and room very clean Friendly staff and plenty of parking"
United States
Amelia
The price is NT$15,006
NT$17,779 total
includes taxes & fees
Aug 20 - Aug 21
Montauk Manor
Iron/ironing board, WiFi (free), individually decorated

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (319 reviews)
"We always stay at the Windward Shores when we go to Montauk. It is a beautiful, clean and comfortable place, and the price is great!"
United States
Joseph
The price is NT$18,485
NT$22,000 total
includes taxes & fees
Aug 25 - Aug 26
Windward Shores Ocean Resort
Apartment | WiFi (free), individually decorated, individually furnished, bed sheets

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (242 reviews)
"Very close to beach"
United States
Rabia
The price is NT$13,749
NT$16,763 total
includes taxes & fees
Jul 29 - Jul 30
Driftwood Resort
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
"Lovely little hotel in the heart of Greenport. Free parking. Nice common areas for hanging out. Walk to numerous bars and restaurants. A nice weekend getaway with a laid back vibe."
Ellen 1-night trip
Posted 2 days ago
Zey Hotel

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Vacation Apartments in Town of Southold Town

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