Town of Southold Town Vacations & Trips from ￥307,573

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.
Aura Hotel Brooklyn

Aura Hotel Brooklyn

4 out of 5
Price was ￥359,914, price is now ￥307,573 per person
￥307,573
per person
Sep 2 - Sep 6
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to New York (JFK)
8/10 Very Good! (1,251 reviews)
property was clean and staff was really friend. look forward to returning.

Reviewed on Jul 20, 2026

Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Price was ￥604,665, price is now ￥406,496 per person
￥406,496
per person
Oct 3 - Oct 11
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8/10 Very Good! (2,471 reviews)
Convenient location and helpful staff.

Reviewed on Jul 19, 2026

Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was ￥394,346, price is now ￥324,013 per person
￥324,013
per person
Oct 4 - Oct 8
found 14 hours ago
Roundtrip flight included
Tokyo (HND) to New York (JFK)
8.8/10 Excellent! (7,595 reviews)
The staff at Hotel St. James were amazing and incredibly accommodating. Although the room was small, it was comfortable and had everything we needed for our one-night stay. The atmosphere throughout the hotel was relaxed and welcoming, making it a pleasant place to stay. We would definitely consider staying here again on a future visit to New York City.

Reviewed on Jul 21, 2026

Aura Hotel Times Square

Aura Hotel Times Square

4 out of 5
Manhattan
Price was ￥366,816, price is now ￥312,393 per person
￥312,393
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.6/10 Excellent! (3,253 reviews)
Our stay was nice. The staff were friendly and helpful . The room was much smaller than expected but it was clean. Also, there isn’t mini fridge or microwave, but there is a safe in the room. It’s in the middle of time square so there are plenty of things to explore without going too far from the hotel. Overall it was a pleasant stay if you want just a nice clean room to sleep in.

Reviewed on Jul 19, 2026

Allegria Hotel

Allegria Hotel

4 out of 5
Price was ￥400,416, price is now ￥343,120 per person
￥343,120
per person
Sep 2 - Sep 6
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to New York (JFK)
8/10 Very Good! (1,330 reviews)
The pool staff was terrific, Mac, Maureen and Rob were very nice and attentive. The staff at the check in desk were very nice, in particular Sharon. As well was Lois in the restaurant.

Reviewed on Jul 21, 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 ￥57,553 per night from Aug 16 to Aug 17
￥57,553
￥79,681 total
Aug 16 - Aug 17
includes taxes & fees
Sound View Greenport
North Fork Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
The price is ￥73,780 per night from Jul 26 to Jul 27
￥73,780
￥84,293 total
Jul 26 - Jul 27
includes taxes & fees
North Fork Resort
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
The price is ￥39,490 per night from Aug 6 to Aug 7
￥39,490
￥45,118 total
Aug 6 - Aug 7
includes taxes & fees
9.2/10 Wonderful! (355 reviews)
"It was quiet & cozy. The rooms were clean"

Reviewed on Jul 20, 2026

Zey Hotel
See all 517 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 ￥307,573. 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.