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

Vacation Rentals in Town of Southold Town

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Top Cities in Town of Southold Town

A pebbled beach at sunset with the sun setting over the horizon.
Vacation RentalsVacation Rentals

Greenport

Greenport

Our top choices for Town of Southold Town vacation rentals

Terrace/patio

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (299 reviews)
"Great condo. Very nice location and grounds."
United States
William
$301 nightly
The price is $344
Nov 29 - Nov 30
Total with taxes and fees
Cliffside Resort Condominiums
A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
United States
Altynai
$302 nightly
The price is $345
Nov 17 - Nov 18
Total with taxes and fees
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, (1,425 reviews)
"We’ve been to Montauk Manor many times. The inside pool area is updated and nice to use. Gavin a restaurant there is quite convenient. The units are comfortable and lovely with fully stocked kitchens."
United States
barbara
$156 nightly
The price is $178
Nov 30 - Dec 1
Total with taxes and fees
Montauk Manor
Terrace/patio

4. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (333 reviews)
"Omg so peaceful and beautiful. Felt like I was in paradise. My fiancee and I enjoyed every moment except checking out because we did not want to leave. Such beauty it was worth the 3 hour car ride. Perfect getaway.💜🙏"
United States
Banessa
$170 nightly
The price is $194
Nov 15 - Nov 16
Total with taxes and fees
Windward Shores Ocean Resort
Private kitchen

5. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.4 out of 10, Very good, (461 reviews)
"The room was very clean and well taken care of."
United States
Mitchell
$146 nightly
The price is $166
Nov 29 - Nov 30
Total with taxes and fees
Montauk Oceanside Suites
Room

6. The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (305 reviews)
"Staff are nice"
United States
na
$668 nightly
The price is $763
Nov 15 - Nov 16
Total with taxes and fees
The Surf Club
A wooden deck with a white round table and two white cushioned chairs.

7. Offshore Spa & Residences

Offshore Spa & Residences
4.5 star property
Downtown Montauk
8.4 out of 10, Very good, (5 reviews)
"What a memorable way to celebrate America’s 250th Anniversary and the Fourth of July at Offshore Montauk. The festive atmosphere, beautiful weather, beach days, and fireworks made for an unforgettable getaway. The property is beautifully designed with thoughtful room layouts, high-end appliances, and quality finishes that create a luxurious yet comfortable experience. The attention to detail throughout the property is impressive, and it's exciting to see the continued improvements being...
United States
Frank
$310 nightly
The price is $354
Nov 15 - Nov 16
Total with taxes and fees
Offshore Spa & Residences
A covered outdoor deck with wicker furniture, a ceiling fan, and a view of a park.

8. Groton Home < 1 Mi to Beach on Long Island Sound!

Groton Home < 1 Mi to Beach on Long Island Sound!
3.0 star property
Groton
$701 nightly
The price is $806
Nov 22 - Nov 23
Total with taxes and fees
Groton Home < 1 Mi to Beach on Long Island Sound!
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
"The shoals was a perfect place for our north fork adventures. The staff was very friendly and extremely accommodating! The location was beautiful and very relaxing."
William 1-night trip
Posted 10 hours ago
The Shoals Suites and Slips

Find out more about Town of Southold Town

Discover your perfect Town of Southold Town vacation rental with Expedia

How many vacation rentals are available in Town of Southold Town?


Expedia has plenty of vacation rentals to choose from in and around  Town of Southold Town, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Town of Southold Town?


The selection of Town of Southold Town vacation rentals we have selected for you start as low as $232 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Town of Southold Town?


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Why should I choose a vacation rental in Town of Southold Town?


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How do I find the best deal on a vacation rental in Town of Southold Town?


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What amenities are available in a vacation rental in Town of Southold Town?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Town of Southold Town vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Town of Southold Town?   


Everytime is a great time to head to Town of Southold Town! Staying in a Town of Southold Town vacation rentals you will always find lots going on to keep you entertained. 


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Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Town of Southold Town vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.