Town of Southold Town Vacations & Trips from ￥427,369

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The Latest Town of Southold Town Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Park Ave NYC

Hotel Park Ave NYC

4.5 out of 5
Manhattan
Price was ￥591,216, price is now ￥427,369 per person
￥427,369
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9/10 Wonderful! (1,408 reviews)
The staff is awesome, the food is delicious, and the rooftop bar and speakeasy both have amazing drinks! My only gripe is that they had no clean face towels during our stay, so we had to use hand towels to shower with. Besides the face towel issue, we had a great stay.

Reviewed on Jul 13, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was ￥708,689, price is now ￥438,143 per person
￥438,143
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9.2/10 Wonderful! (3,652 reviews)
Check in and check out front desk staff wasn't friendly.

Reviewed on Jul 14, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was ￥698,844, price is now ￥433,632 per person
￥433,632
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9/10 Wonderful! (3,130 reviews)
Clean, and friendly staff

Reviewed on Jul 13, 2026

WestHouse New York

WestHouse New York

5 out of 5
Manhattan
Price was ￥630,826, price is now ￥440,020 per person
￥440,020
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
8.4/10 Very Good! (1,007 reviews)
Very friendly staff. Quiet hotel. Clean. Walking distance to all the Broadway shows we saw! Would stay here again!

Reviewed on Jul 13, 2026

Washington Square Hotel

Washington Square Hotel

3.5 out of 5
Manhattan
Price was ￥606,798, price is now ￥430,190 per person
￥430,190
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9.2/10 Wonderful! (1,303 reviews)
My favorite place to stay when in Greenwich Village. Always kind helpful staff and clean rooms. Our a/c stopped working and we were immediately placed in a room where the a/c was working.

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
The price is ￥88,332 per night from Aug 12 to Aug 13
￥88,332
￥114,839 total
Aug 12 - Aug 13
includes taxes & fees
8.4/10 Very Good! (665 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 ￥46,055 per night from Aug 11 to Aug 12
￥46,055
￥52,618 total
Aug 11 - Aug 12
includes taxes & fees
9.2/10 Wonderful! (350 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
North Fork Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
The price is ￥60,477 per night from Jul 20 to Jul 21
￥60,477
￥69,096 total
Jul 20 - Jul 21
includes taxes & fees
9.4/10 Exceptional! (30 reviews)
"Overall the stay was pleasant. The cottages are well maintained. This property is still developing so there was active construction. It listed some amenities that were not yet available and some that were only available through a weekend stay which we did not have with a Sunday-Tuesday booking. I ..."

Reviewed on Jul 8, 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 ￥427,369. 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.