Town of Southold Town Holidays

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Top destinations in Town of Southold Town

Greenport Harbour
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Greenport

Greenport

Top hotels in Town of Southold Town

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is 6.025.156 ₫ per night from 27 May to 28 May
6.025.156 ₫
9.141.758 ₫ total
27 May - 28 May
includes taxes & fees
8.4/10 Very Good! (642 reviews)
friendly staff, great sunset

Reviewed on 30 Apr 2026

Sound View Greenport
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
The price is 6.379.577 ₫ per night from 12 May to 13 May
6.379.577 ₫
8.643.392 ₫ total
12 May - 13 May
includes taxes & fees
8.8/10 Excellent! (594 reviews)
Spacious, well appointed rooms. Great location. The complimentary breakfast was cozy (nothing fancy but gets the job done). We stayed for three nights with a small dog in tow. The only surprise was that parking was not free ($29 per night) but there was plenty of free street parking available ...

Reviewed on 27 Apr 2026

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 5.741.619 ₫ per night from 14 May to 15 May
5.741.619 ₫
7.218.575 ₫ total
14 May - 15 May
includes taxes & fees
9.4/10 Exceptional! (265 reviews)
My girlfriend and I stayed in April and it was amazing stay. Rooms are outstanding, one of the best rooms we ever stayed, and location was stunning. Beautiful marina, great waterfront views from the property. It was so quiet and relaxing. We went to Greenport for dinners. 10$ Breakfast cards were ...

Reviewed on 25 Apr 2026

The Shoals Suites and Slips
See all 542 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 holiday package cost?
Tailor make your Town of Southold Town holiday 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 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 1null000null000 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.

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