Town of Southold Town Vacation Packages
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Top vacation destinations in Town of Southold Town
Orient
Top Town of Southold Town Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Town of Southold Town Hotel Deals
Sound View Greenport
58775 County Rd 48 Greenport NY
CA $324
CA $410 total
Oct 1 - Oct 2
includes taxes & fees
8.4/10 Very good! (712 reviews)
"I booked thru Expedia but never checked in because you were SOLD OUzt! Expedia has a problem to fix!"
Reviewed on Sep 2, 2026
The Shoals Suites and Slips
61600 Main Rd Southold NY
CA $280
CA $355 total
Oct 1 - Oct 2
includes taxes & fees
9.4/10 Exceptional! (333 reviews)
"Our room was clean and very spacious, the bathroom was large and modern. They setup a food shed outside with a nice menu and bar where you can sit down and have fresh oysters for example and a drink when returning from the wineries all day. The staff outside was super friendly. However, here are ..."
Reviewed on Sep 2, 2026
Zey Hotel
439 Main Street Greenport NY
CA $234
CA $267 total
Sep 7 - Sep 8
includes taxes & fees
9.2/10 Wonderful! (394 reviews)
"Great location, and James is there for your every need! Not posh, but great value and a friendly staff make for a great experience in Greenport!"
Reviewed on Sep 2, 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 vacation package cost?
Tailor make your Town of Southold Town vacation package from only CA $1,331. 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
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 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.
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.
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 carefree afternoon at 67 Steps Beach during your travels in Greenport? Take in the festivals and sunsets in the area.
Harbes Family Farm
10.0/10 (2 reviews)
You can search for that perfect souvenir at Harbes Family Farm during your trip to Mattituck. While you're in the area, stroll along the beautiful beaches.
Raphael Winery
You can enjoy a tasting or tour at Raphael Winery during your travels to Peconic. Wander the beaches or discover the area's sunsets.
What to do in Town of Southold Town
Mystic Seaport Museum Adventure
CA $48
per adult
92% of travellers recommend
Spirits of Mystic: Cocktail Pub Crawl
CA $138
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
