Town of Southold Town Vacations & Trips from ￥298,968

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The Latest Town of Southold Town Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Manhattan
Price was ￥415,525, price is now ￥298,968 per person
￥298,968
per person
May 22 - May 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (1,755 reviews)
Not bad acces to Times Square but old building and smelled like smoke in the room.

Reviewed on Mar 11, 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was ￥1,227,177, price is now ￥780,592 per person
￥780,592
per person
May 22 - May 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,001 reviews)
Excellent stay, very clean spacious rooms. Location is great - close to everything. Only downfall was the bathroom, very tiny with a pedestal sink right next to the toilet, not great for women who need to get ready.

Reviewed on Feb 24, 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 ￥521,913, price is now ￥340,464 per person
￥340,464
per person
May 22 - May 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,419 reviews)
Excellent location & staff very helpful. Only drawback was elevators. Early mornings there was only 1 operating in mornings from 6-10:00am. They used other 2 to transport people to 5th floor.(restaurant location.). Had to walk down 12 flights to make my breakfast reservation. Couldn’t get on the one elevator that was available.

Reviewed on Mar 9, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was ￥481,160, price is now ￥321,258 per person
￥321,258
per person
May 22 - May 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,923 reviews)
Great location, clean, courteous staff, breakfast buffet had lots of options. Would definately stay again.

Reviewed on Mar 5, 2026

Empire Hotel

Empire Hotel

4 out of 5
Manhattan
Price was ￥630,668, price is now ￥465,043 per person
￥465,043
per person
May 11 - May 18
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (HND) to Newark Liberty Intl. Airport (EWR)
7.6/10 Good! (6,724 reviews)
It is definitely an older hotel; overall, great option hotel for Lincoln Square. Lots of food options and shops around. The hotel is foodless, no snacks, drinks, nor breakfast. My only upset is that the entire hotel lacks microwaves. I had most of my amazing lasagna from Cafe Friellos stored in the fridge but no way of heating it up. Bummer.

Reviewed on Mar 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 ￥24,193 per night from Mar 25 to Mar 26
￥24,193
￥32,156 total
Mar 25 - Mar 26
includes taxes & fees
8.4/10 Very Good! (620 reviews)
Staff was over the top helpful, nice!!!! If you needed help or anything they were right on it for you Thank you do very much for making a sad trip for a loved ones memorial into something grateful!!

Reviewed on Mar 1, 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 ￥21,209 per night from Mar 15 to Mar 16
￥21,209
￥28,746 total
Mar 15 - Mar 16
includes taxes & fees
8.8/10 Excellent! (572 reviews)
Room was clean, climate control worked well kept room comfortable, bathroom was nice. Only thing I would suggest would be a complementary bottle of water for each guest.

Reviewed on Mar 10, 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 ￥22,715 per night from Mar 19 to Mar 20
￥22,715
￥25,952 total
Mar 19 - Mar 20
includes taxes & fees
9.4/10 Exceptional! (244 reviews)
Very friendly

Reviewed on Mar 6, 2026

The Shoals Suites and Slips
See all 537 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 ￥298,968. 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.