Town of Southold Town Vacations & Trips from ₩749,109

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The Latest Town of Southold Town Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Arthouse Hotel New York City

Arthouse Hotel New York City

4 out of 5
Manhattan
Price was ₩1,015,128, price is now ₩749,109 per person
₩749,109
per person
Aug 18 - Aug 20
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)
8.8/10 Excellent! (2,013 reviews)
La estadía estuvo buena ya que está en una zona estratégica , lastimosamente siento que lo que ponen en fotos en la plataforma no es nada que ver a lo que realmente te dan al momento de check in, son habitaciones super básicas y pequeñas

Reviewed on Jul 9, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was ₩1,378,117, price is now ₩967,205 per person
₩967,205
per person
Aug 18 - Aug 20
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)
9.2/10 Wonderful! (3,652 reviews)
Overall nice hotel however they surprise you with a $100 resort fee, also they hold a $150 security fee on your card. I was aware of the second fee, I may have missed the first one. The breakfast was decent with a variety of items to choose from, the baked beans was unusual to me for breakfast 😂there isn’t a restaurant but a combo bar & grill. There is another hotel of the same name in the immediate area but this is the nicer one so pay attention when making your reservation. Instead of taking taxis or Uber I would suggest using TopView bus tours they are a great value for traveling around Manhattan.

Reviewed on Jul 9, 2026

Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was ₩1,032,393, price is now ₩752,160 per person
₩752,160
per person
Aug 18 - Aug 20
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)
8.8/10 Excellent! (7,519 reviews)
The place smelled from when you get in till inside the room. Like garbage and a mix of cigarettes and alcohol

Reviewed on Jul 10, 2026

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was ₩1,088,074, price is now ₩794,326 per person
₩794,326
per person
Aug 18 - Aug 20
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)
9.2/10 Wonderful! (2,253 reviews)
I am disappointed. I was organizing my bags and realized that items and belongings were missing, such as 4 empty bags and a bag containing a T-shirt and three reading glasses. This had never happened to me before, and so far no one has given me any explanation about what happened. I am Waiting for an answer.

Reviewed on Jul 9, 2026

The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
Price was ₩955,564, price is now ₩758,263 per person
₩758,263
per person
Aug 18 - Aug 20
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)
9/10 Wonderful! (2,053 reviews)
I love the location to be near my daughter in Murray hill. I didn’t like that I arrived at 9:30am on a Tuesday and they didn’t let me check in early even though rooms were available. She said it would be an early check in charge. I usually stay at Bonvoy properties and that would never happen. The room was fine. The bed and pillows very comfortable and the halls clean. Lobby nice sitting areas and friendly staff at the door. Overall good

Reviewed on Jul 10, 2026

Town of Southold Town Hotel Deals

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is ₩713,702 per night from Jul 22 to Jul 23
₩713,702
₩944,836 total
Jul 22 - Jul 23
includes taxes & fees
8.4/10 Very Good! (664 reviews)
"The staff was helpful and nice. The exterior of the property was fine and the landscaping pretty. However the room was awful - not particularly clean, a noisy, wall ac plugged in next to the bed, felt like a renovated motel room. Sorry not worth $700/ night."

Reviewed on Jul 8, 2026

Sound View Greenport
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
The price is ₩428,221 per night from Aug 10 to Aug 11
₩428,221
₩489,243 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (346 reviews)
"We absolutely adored the Zey hotel. What a gem in the very heart of Greenport! Super clean and comfortable. All the staff were welcoming and accommodating. Eclectic design was so refreshing and fun. We highly recommend Zey hotel and look forward to staying there in the future. Thank you for making ..."

Reviewed on Jul 8, 2026

Zey Hotel
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is ₩561,581 per night from Jul 21 to Jul 22
₩561,581
₩679,367 total
Jul 21 - Jul 22
includes taxes & fees
9.4/10 Exceptional! (292 reviews)
"Had an amazing stay here during the off season with our newborn. The room was clean and grounds were beautifully maintained. Can’t wait to come back here this summer to see the property in full action."

Reviewed on Jul 8, 2026

The Shoals Suites and Slips
See all 510 properties in Town of Southold Town
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.

Frequently asked questions

How much does a Town of Southold Town vacation package cost?
Tailor make your Town of Southold Town vacation package from only ₩749,109. Pick from any combination of flights, hotels and rental cars to put together the trip you've been dreaming about for ages. Don't forget to add on a few experiences or activities!
How do I get a cheap travel package to Town of Southold Town?
Bundling your hotel and flight with Expedia won't just save you time — it'll save you a nice amount too. A Town of Southold Town vacation package makes it a cinch to put together your dream adventure. With more than 550 airlines throughout the world to choose from, finding flights that fit your schedule won't be a challenge. Not only that, we have over 1,000,000 hotels globally to select from. Talk about choice! Whatever your budget, Expedia puts the world within your reach.
Where should I stay in Town of Southold Town?
With popular attractions such as 67 Steps Beach and Orient Point County Park in this area, look for a hotel located near either one. Macari Vineyards is another Town of Southold Town hot spot that pulls the crowds.
What are the top hotels in Town of Southold Town?
If you intend to stay in the Greenport West neighborhood, some great options are The Harborfront Inn and Sound View Greenport. Pipes Cove is another well-known Town of Southold Town area. We recommend Zey Hotel or The Menhaden if you prefer this part of town.
How far in advance should I book my Town of Southold Town vacation?
It depends on the air carrier, but it's usually possible to browse through international flights on Expedia nearly a year in advance. While it's generally a good idea to book ahead of time, lucky customers will occasionally find a cheaper seat only weeks before their intended journey.
What does an Expedia Town of Southold Town travel package include?
Travel packages include hotels, rental cars and flights, but you can combine any of them to create your ideal Town of Southold Town vacation. You can also add on a few activities and tours once you've made your booking. You're in the driver's seat! When you combine your bookings with Expedia, you'll get discounts you won't find elsewhere.
What should I know before booking a Town of Southold Town travel package?
You'll land amazing savings when you combine your flights, hotels and rental cars into a travel package. Not just that, booking everything in one place simply makes planning easier. So why waste money or time? Whether you're organizing an upscale romantic escape or a budget family adventure, have a look at our vacation packages today.
Can I choose my airline with a Town of Southold Town Expedia vacation package?
Yes — that's one of the best things about an Expedia package. You can mix and match your flights, hotels and more. We have access to more than 550 partner airlines throughout the world, so you have options galore when creating your Town of Southold Town escape.
If I'm not able to travel, can I cancel my Town of Southold Town vacation package?
We totally understand — life can throw you the odd curveball. If you've booked a Town of Southold Town vacation package and need to amend or cancel it, we can help. It's always worth checking out our Customer Service Portal first for information. But generally, if you've taken out your package in the last 24 hours, you may be able to amend or cancel your itinerary free of charge. If it's been longer than 24 hours, your airline, hotel or car rental company may charge a fee.

Stay near popular Town of Southold Town attractions

A rocky shoreline with large boulders and a calm sea.

Orient Point County Park

10.0/10 (1 review)
Explore the great outdoors at Orient Point County Park, a lovely green space in Orient Point. Stroll along the beaches or discover the area's sunsets.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.