Town of Southold Town Vacations & Trips from ￥373,764

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The Latest Town of Southold Town Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Price was ￥534,324, price is now ￥373,764 per person
￥373,764
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to New York (JFK)
8/10 Very Good! (2,471 reviews)
Helpful staff and the rooms are very nice

Reviewed on Jul 10, 2026

5th & 55th Residence Club

5th & 55th Residence Club

5 out of 5
Manhattan
Save 100% on your flight
Price was ￥1,737,597, price is now ￥1,104,998 per person
￥1,104,998
per person
Sep 19 - Sep 26
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.4/10 Very Good! (5 reviews)

The High Line Hotel

The High Line Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was ￥793,356, price is now ￥546,458 per person
￥546,458
per person
Sep 19 - Sep 26
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.6/10 Excellent! (1,006 reviews)
The central air in Room 56 was not working, & someone put in a window air conditioner. The room was 75 degrees because heat was coming in from the side of the window unit. It was over 100degrees on July 4th. Luckily we were able to change rooms and Room 22 was nice & cool. The staff is lovely!

Reviewed on Jul 9, 2026

Hotel Beacon

Hotel Beacon

4 out of 5
Manhattan
Price was ￥640,978, price is now ￥448,105 per person
￥448,105
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
9.4/10 Exceptional! (1,490 reviews)
Room was always clean and staff was helpful.

Reviewed on Jul 6, 2026

Hotel AKA NoMad

Hotel AKA NoMad

4 out of 5
Manhattan
Save 100% on your flight
Price was ￥811,379, price is now ￥574,417 per person
￥574,417
per person
Sep 19 - Sep 26
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
.

Reviewed on Jul 6, 2026

Town of Southold Town Hotel Deals

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
8.4/10 Very Good! (664 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

Get rates
Sound View Greenport
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
The price is ￥45,836 per night from Aug 10 to Aug 11
￥45,836
￥52,368 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (346 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
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is ￥60,111 per night from Aug 3 to Aug 4
￥60,111
￥72,718 total
Aug 3 - Aug 4
includes taxes & fees
9.4/10 Exceptional! (292 reviews)
"Had an amazing stay here during the off season with our newborn. The room was clean and grounds were beautifully maintained. Can’t wait to come back here this summer to see the property in full action."

Reviewed on Jul 8, 2026

The Shoals Suites and Slips
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 ￥373,764. 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
Paranormal Pub Crawl: Beer Tour

Paranormal Pub Crawl: Beer Tour

￥12,191
per adult
Paranormal Pub Crawl: Beer Tour
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.