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

Flat-screen TV

1. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (54 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is NT$10,167
NT$11,616 total
includes taxes & fees
Sep 15 - Sep 16
North Fork Resort
Condo | Terrace/patio

2. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (292 reviews)
"Great place!"
United States
Christine
The price is NT$9,143
NT$13,266 total
includes taxes & fees
Oct 5 - Oct 6
Cliffside Resort Condominiums
Iron/ironing board, WiFi (free), individually decorated

3. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (323 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 NT$3,764
NT$5,161 total
includes taxes & fees
Oct 12 - Oct 13
Windward Shores Ocean Resort
Apartment | WiFi (free), individually decorated, individually furnished, bed sheets

4. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
8.8 out of 10, Excellent, (249 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
The price is NT$5,177
NT$6,945 total
includes taxes & fees
Oct 5 - Oct 6
Driftwood Resort
Lobby

5. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,401 reviews)
"Beautiful property"
United States
John
The price is NT$4,082
NT$5,283 total
includes taxes & fees
Oct 12 - Oct 13
Montauk Manor
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
"Our stay was filled with quietness set in a backdrop of beautiful blue skies enveloping the peconic bay. What a great place to come apart and forget about the stress of the week, relax and unwind. My husband and I were pleased with our stay. Everyone was ao friendly and helpful Mario was very attentive to our requests. Thenk you, Mario! A few suggestions: . Blinds at the living room sliding window in addition to the curtains to create more privacy . A microwave in the rooms since the stove/oven is not hooked up . Possibly changing your WIFI provider to ensure the TV works without buffering interruption Thank you so much. We recommend this hotel for anyone wanting to come apart and rest in serenity."
Nina 3-night trip
Posted less than an hour ago
The Shoals Suites and Slips

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