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

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Our top choices for Town of Southold Town holiday rentals

Terrace/patio

1. 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 ₹22,644
₹36,519 total
includes taxes & fees
28 Oct - 29 Oct
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, (61 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is ₹24,718
₹28,240 total
includes taxes & fees
8 Oct - 9 Oct
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, (1,409 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is ₹12,382
₹16,026 total
includes taxes & fees
28 Oct - 29 Oct
Montauk Manor
Room

4. 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 ₹11,258
₹15,989 total
includes taxes & fees
6 Oct - 7 Oct
Driftwood Resort
Room

5. 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 ₹11,417
₹15,654 total
includes taxes & fees
25 Oct - 26 Oct
Windward Shores Ocean 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

North Fork Resort

North Fork Resort

10/10 Excellent
"Fantastic contemporary cottage. Looks brand new and it has everything. Wonderful place to stay. Check in process needs improvement with more attention paid to details by staff."
marie 1-night trip
Posted 15 hours ago
North Fork Resort

Find out more about Town of Southold Town

Holiday Apartments in Town of Southold Town

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