Town of Southold Town Holidays
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Top destinations in Town of Southold Town
Orient
Town of Southold Town Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Top hotels in Town of Southold Town
Sound View Greenport
58775 County Rd 48 Greenport NY
S$444
15 Sept - 16 Sept
includes taxes & fees
8.4/10 Very good! (703 reviews)
"The property is well maintained and the location is perfect, however, there were some downsides during our stay. My fiancé, our dog, and I went to this hotel as it's a pet-friendly location, on their website they advertised amenities for pets (i.e, Yeti dog bowl(s), plush bed) but we never received ..."
Reviewed on 24 Aug, 2026
North Fork Resort
690 Queen St Greenport NY
S$435
7 Sept - 8 Sept
includes taxes & fees
9.6/10 Exceptional! (50 reviews)
"THERE WAS ONLY ONE THING. THE LAST MORNING THERE WAS NO HOT H2O HOWEVER THE PROBLEM WAS FIXED."
Reviewed on 20 Aug, 2026
Zey Hotel
439 Main Street Greenport NY
S$294
7 Sept - 8 Sept
includes taxes & fees
9.2/10 Wonderful! (386 reviews)
"Staff was accommodating and kind. The coffee and tea is a nice touch. Great location and nice common areas. Free parking. The room was a little shoddy, especially the bathroom but products were nice. They really need to dilute the cleaning products though. Way too strong of a smell in the linens ..."
Reviewed on 24 Aug, 2026
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 holiday package cost?
Tailor make your Town of Southold Town holiday package from only S$2,204. 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 holiday 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 neighbourhood, 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 holiday?
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 holiday. 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 organising an upscale romantic escape or a budget family adventure, have a look at our holiday packages today.
Can I choose my airline with a Town of Southold Town Expedia holiday 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 holiday package?
We totally understand — life can throw you the odd curveball. If you've booked a Town of Southold Town holiday 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
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.
Photo by 4 Star Traveler
Pindar Vineyards
8.4/10 (8 reviews)
You can enjoy a tasting or tour at Pindar Vineyards during your travels to Peconic. Discover the area's sunsets and wineries.
Photo by Joe Vickiana
Orient Beach State Park
8.6/10 (33 reviews)
You can take time to visit Orient Beach State Park during your travels to Orient. Stroll along the waterfront or discover the area's sunsets.
Photo by Adriana T
Bedell Cellars
8.6/10 (4 reviews)
You can enjoy a tasting or tour at Bedell Cellars during your travels to Cutchogue. While you're in the area, stroll along the beautiful beaches.
Macari Vineyards
8.0/10 (1 review)
You can enjoy a tasting or tour at Macari Vineyards during your travels to Mattituck. While you're in the area, stroll along the beautiful beaches.
Kontokosta Winery
9.2/10 (48 reviews)
You can enjoy a tasting or tour at Kontokosta Winery during your travels to Greenport West. Wander the beautiful beaches in this family-friendly area.
67 Steps Beach
9.6/10 (26 reviews)
Why not spend a care-free afternoon at 67 Steps Beach during your travels in Greenport? Take in the festivals and sunsets in the area.
Peconic Bay Winery
You can enjoy a tasting or tour at Peconic Bay Winery during your travels to Cutchogue. While you're in the area, stroll along the beautiful beaches.
What to do in Town of Southold Town
Mystic Seaport Museum Adventure
S$52
per adult
92% of travellers recommend
The Hamptons and Long Island Wineries Private Tour
S$1,674
per traveller
Full Day Private Long Island Wine Tours from New York City
S$244
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
