Town of Southold Town Vacations & Trips from ￥309,267

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Town of Southold Town Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was ￥467,692, price is now ￥309,267 per person
￥309,267
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to New York (JFK)
8.6/10 Excellent! (2,498 reviews)
My comforter was stained and so was the window shade. The shower faucet was broken. An item was stolen from my room and when I reported it to the manager, he told me it was “Not his problem”

Reviewed on Jul 17, 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was ￥1,067,264, price is now ￥686,426 per person
￥686,426
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to New York (JFK)
9/10 Wonderful! (1,002 reviews)

The Iroquois New York

The Iroquois New York

4.5 out of 5
Manhattan
Save 100% on your flight
Price was ￥792,002, price is now ￥579,693 per person
￥579,693
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to New York (JFK)
9.4/10 Exceptional! (1,760 reviews)
In a very convenient location

Reviewed on Jul 15, 2026

Hotel Beacon

Hotel Beacon

4 out of 5
Manhattan
Price was ￥628,211, price is now ￥461,873 per person
￥461,873
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to New York (JFK)
9.4/10 Exceptional! (1,492 reviews)
Comfortable and clean, upgraded to suite which was appreciated! Great neighborhood, easy access into Central Park and Fairway market across the street. Was there with family decades ago, just as nice this time with sister!

Reviewed on Jul 16, 2026

The Hoxton, Williamsburg

The Hoxton, Williamsburg

4 out of 5
Price was ￥537,881, price is now ￥399,234 per person
￥399,234
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
The hotel was great. The food was amazing. We ate at laser Wolf. It was a really fun experience. The restaurants were great. The staff was great. The room was very well appointed but very small very very small and there was no gym in the building and they say they have an arrangement with a gym nearby which they do and it’s wonderful, but it does cost $25 a visit so if you’re going to work out every day it’s going to be expensive. Otherwise, we had a wonderful stay.

Reviewed on Jul 14, 2026

Town of Southold Town Hotel Deals

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
Get rates
Sound View Greenport
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
The price is ￥39,453 per night from Aug 17 to Aug 18
￥39,453
￥45,076 total
Aug 17 - Aug 18
includes taxes & fees
9.2/10 Wonderful! (354 reviews)
"The hotel has a European flair - nice room, small but comfortable bed. Lots of spread out space in community rooms throughout the hotel main floor. Private parking in the back. Convenient location. Make your own coffee (pods) and maybe a muffin if you are lucky. No elevator."

Reviewed on Jul 16, 2026

Zey Hotel
North Fork Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
The price is ￥78,986 per night from Aug 9 to Aug 10
￥78,986
￥90,242 total
Aug 9 - Aug 10
includes taxes & fees
9.4/10 Exceptional! (32 reviews)
"Amazing. We stayed in a 2 bedroom cabin. Absolutely clean is all I can say. Rivaling some big hotel chains i have stayed in. I will return for sure in the future."

Reviewed on Jul 16, 2026

North Fork Resort
See all 511 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 ￥309,267. 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.
See properties

What to do in Town of Southold Town

Downtown Westerly Ghost Tour

Downtown Westerly Ghost Tour

￥5,689
per adult
100% of travellers recommend
Downtown Westerly Ghost Tour
Mystic: Guided Ghost Tour of Downtown Mystic at Night

Mystic: Guided Ghost Tour of Downtown Mystic at Night

￥5,689
per adult
94% of travellers recommend
Mystic: Guided Ghost Tour of Downtown Mystic at Night
great fun with friends

Full Day Private Long Island Wine Tours from New York City

￥30,720
per adult
Full Day Private Long Island Wine Tours from New York City
See all activities in Town of Southold Town
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.