Town of Southold Town Vacations & Trips from ￥248,675

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The Latest Town of Southold Town Vacation Packages

Price found within the past 48 hours. Click for updated prices.
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was ￥337,330, price is now ￥248,675 per person
￥248,675
per person
Apr 19 - Apr 23
found 5 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
Great location would 100% come back

Reviewed on Jan 22, 2026

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
Price was ￥796,552, price is now ￥511,439 per person
￥511,439
per person
Mar 8 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to New York (JFK)
9/10 Wonderful! (1,723 reviews)
Everything was excellent!!

Reviewed on Jan 23, 2026

The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
Price was ￥534,644, price is now ￥364,520 per person
￥364,520
per person
Mar 8 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to New York (JFK)
9/10 Wonderful! (1,825 reviews)
The hotel is excellent: very clean with exceptionally helpful staff. The rooftop restaurant and bar offer a lovely setting for dining and cocktails.

Reviewed on Jan 22, 2026

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was ￥623,620, price is now ￥470,820 per person
￥470,820
per person
Apr 12 - Apr 18
found 8 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to New York (JFK)
9.8/10 Exceptional! (1,411 reviews)
The room was amazing and the staff was also great, the room was also in a perfect location. There was also a fantastic view from the room.

Reviewed on Jan 22, 2026

EVEN Hotel Brooklyn by IHG

EVEN Hotel Brooklyn by IHG

4 out of 5
Price was ￥386,408, price is now ￥299,740 per person
￥299,740
per person
Mar 16 - Mar 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
8.6/10 Excellent! (1,626 reviews)
The location is convenience to me, but it is very noisy when the room is facing the street on a lower floor. The staffs are very nice and helpful.

Reviewed on Jan 20, 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 ￥21,255 per night from Jan 26 to Jan 27
￥21,255
￥28,811 total
Jan 26 - Jan 27
includes taxes & fees
8.4/10 Very Good! (607 reviews)
This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...

Reviewed on Jan 10, 2026

Sound View Greenport
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
The price is ￥18,568 per night from Jan 28 to Jan 29
￥18,568
￥25,739 total
Jan 28 - Jan 29
includes taxes & fees
8.8/10 Excellent! (562 reviews)
The staff was wonderful and the room and views fantastic.

Reviewed on Jan 12, 2026

The Harbor Front Inn
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is ￥22,855 per night from Jan 25 to Jan 26
￥22,855
￥26,111 total
Jan 25 - Jan 26
includes taxes & fees
9.4/10 Exceptional! (236 reviews)
The streaming TV service was confusing

Reviewed on Jan 19, 2026

The Shoals Suites and Slips
See all 531 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 ￥248,675. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.