Town of Southold Town Vacations & Trips

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Top destinations in Town of Southold Town

Tranquil evening seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA
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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 NT$8,565 per night from May 26 to May 27
NT$8,565
NT$12,498 total
May 26 - May 27
includes taxes & fees
8.4/10 Very Good! (647 reviews)
"They charged us for parking in front of our room. Unbelievable. We stayed there in April, off season, the motel was empty."

Reviewed on 2026/5/11

Sound View Greenport
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
The price is NT$7,949 per night from May 25 to May 26
NT$7,949
NT$10,709 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (600 reviews)
"This is a beautiful place in a great town. Greenport has much to recommend it. Excellent restaurants, interesting shopping, and congenial places to hang around, have a drink, a pastry or coffee. The seafood, from shellfish to the top of the maritime food chain is fresh and abundant, and generally ..."

Reviewed on 2026/5/17

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 NT$10,129 per night from Jun 11 to Jun 12
NT$10,129
NT$12,363 total
Jun 11 - Jun 12
includes taxes & fees
9.4/10 Exceptional! (269 reviews)
"Very helpful staff. Room was very roomy (no pun intented) and appeared to be recently upgraded. Chit provided for continental breakfast at a local coffee shop that was very good. Definitely recommend."

Reviewed on 2026/5/5

The Shoals Suites and Slips
See all 531 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 . 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.