Town of Southold Town Vacations & Trips from ￥391,790

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.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was ￥588,421, price is now ￥391,790 per person
￥391,790
per person
Sep 3 - Sep 9
found 2 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to New York (JFK)
9/10 Wonderful! (3,130 reviews)
Staff are nice and helpful. Room is clean but noisy at night. Hotel doesn’t provide slippers creating inconvenience.

Reviewed on Jul 11, 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 ￥714,840, price is now ￥477,590 per person
￥477,590
per person
Sep 18 - Sep 24
found 1 day ago
Roundtrip flight included
Tokyo (HND) to New York (JFK)
9.2/10 Wonderful! (3,652 reviews)
We love this hotel, the staff is so helpful, rooms are big and beds so comfortable, can’t wait to go back

Reviewed on Jul 12, 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 7 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9.2/10 Wonderful! (1,303 reviews)
Location is excellent - near lots of great walkable restaurants and the subway is close by. The staff is welcoming and attentive. The hotel provided a light continental breakfast which was fine. The building is dated which is a double-edged sword. The architectural details are charming; however, the age of the building made for a few annoyances—the room was lacking in tight, plentiful electrical outlets so it took a long time to recharge phones, etc. My bathroom did not have a vent fan so maintenance had to crack open the large window to defog the mirror and there was a short in the bathroom light. On the plus side, the a/c cooled the room quickly and the water pressure was robust. I believe the hotel is undergoing a rolling renovation so I would stay here again.

Reviewed on Jul 12, 2026

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 7 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9/10 Wonderful! (1,408 reviews)
Lovely little hotel in a great location. The experience is that of a cool little boutique hotel. Self checkin, greeted with a welcome glass of champagne, complementary soft mini bar and snacks. Ability to communicate with staff by text was ideal. Quick service to address anything that may come up. Bed was very comfortable and the floor was quiet. I’m not sure why the app is telling me to review a balcony as there wasn’t one. The only recommendation would be to run a dehumidifier- the carpets had a lingering damp smell. Overall the location, experience was great.

Reviewed on Jul 12, 2026

The Langham, New York, Fifth Avenue

The Langham, New York, Fifth Avenue

5 out of 5
Manhattan
Save 100% on your flight
Price was ￥1,053,908, price is now ￥774,506 per person
￥774,506
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to New York (JFK)
9.6/10 Exceptional! (1,001 reviews)
The Langham NYC is truly a home away from home. From the moment we left our car, to the check-in, the club lounge staff, etc, everyone is trying their best to make us feel welcomed. It makes travelling so much more pleasurable when you know that even the tiniest details will be taken care of. Our room was spacious. The club lounge, in my humble opinion, is a star. It’s so nice after a day packed full of activities to come to the lounge to “wine-down” or “champagne-down” I also enjoyed meeting like minded guests at the lounge to have a great conversation All-in-all, an excellent hotel and calming experience, a bit of a hideout from the overstimulating nature of NYC

Reviewed on Jul 9, 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 ￥105,355 per night from Jul 26 to Jul 27
￥105,355
￥134,223 total
Jul 26 - Jul 27
includes taxes & fees
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

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 5 to Aug 6
￥45,836
￥52,368 total
Aug 5 - Aug 6
includes taxes & fees
9.2/10 Wonderful! (347 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 Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
The price is ￥76,394 per night from Jul 14 to Jul 15
￥76,394
￥95,592 total
Jul 14 - Jul 15
includes taxes & fees
8.8/10 Excellent! (624 reviews)
"Absolutely perfect stay at the Harbor Front. The staff are all absolute gems! One of the front desk people even waited for us with towels when we got caught in a massive sudden summer storm! Pool was also excellent, and we were able to spend time at the sister property, Soundview. All in all a wonderful ..."

Reviewed on Jul 11, 2026

The Harbor Front Inn
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 ￥391,790. 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.