Town of Southold Town Holidays

Book a Hotel + Flight or Car together to unlock savings

Top destinations in Town of Southold Town

FlightsFlightsHotelsHotels

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 12.206.400 ₫ per night from 21 Aug to 22 Aug
12.206.400 ₫
15.293.834 ₫ total
21 Aug - 22 Aug
includes taxes & fees
8.4/10 Very Good! (542 reviews)
"Every room comes with an ocean view, steps down to the beach. Activities at night. Band at the ocean on certain nights. Will be back every year! Help with bags and getting to room by golf cart."

Reviewed on 22 Jul 2025

Sound View Greenport
Greenporter Hotel

Greenporter Hotel

2 out of 5
326 Front St, Greenport, NY
9.2/10 Wonderful! (146 reviews)
"Great place to get away and relax. The staff were very friendly and helpful. Wondering why the restaurant and bar were closed?"

Reviewed on 28 Jul 2025

Get rates
Greenporter Hotel
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St, Greenport, NY
The price is 9.898.952 ₫ per night from 27 Aug to 28 Aug
9.898.952 ₫
12.657.576 ₫ total
27 Aug - 28 Aug
includes taxes & fees
8.6/10 Excellent! (492 reviews)
"My only issue was the bed pillows need updating. They weren’t very comfortable, felt old and were faded."

Reviewed on 22 Jul 2025

The Harbor Front Inn
See all 561 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.