Town of Southold Town Holidays

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Your Town of Southold Town Holiday

Leave the travel planning up to us with a Town of Southold Town holiday package. With everything organised before you leave, all you'll have to do is sit back, chill out and enjoy this destination's wonders to the fullest. Get your trip to Town of Southold Town off to a flying start by making New Suffolk the first stop. This is a popular city with travellers from all over. Whether you're planning to travel on a shoestring or want to splurge, Expedia are here to help you organise your next Town of Southold Town holiday.

Top destinations in Town of Southold Town

A calm lake with a forest in the background during sunset.
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Southold

Southold

Top Town of Southold Town Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn New York/Manhattan-Midtown East

Hilton Garden Inn New York/Manhattan-Midtown East

3.5 out of 5
Manhattan
Save 100% on your flight
Price was £1,815, price is now £1,208 per person
£1,208
per person
12 Sept - 17 Sept
found 1 day ago
Return direct flight included
London (LGW) to Newark Liberty Intl. Airport (EWR)
7.8/10 Good! (1,737 reviews)
Very good

Reviewed on 30 Jun 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was £3,848, price is now £2,341 per person
£2,341
per person
3 Sept - 7 Sept
found 1 day ago
Return flight included
London (LON) to New York (JFK)
9/10 Wonderful! (1,000 reviews)
Nicely designed hotel with beautiful views. Staff was very nice but service was generally slow.

Reviewed on 28 Jun 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was £2,083, price is now £1,314 per person
£1,314
per person
13 Aug - 20 Aug
found 8 hours ago
Return flight included
London (LHR) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (3,099 reviews)
Excellent service snd breakfast

Reviewed on 30 Jun 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was £1,981, price is now £1,252 per person
£1,252
per person
12 Sept - 17 Sept
found 1 day ago
Return direct flight included
London (LGW) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,632 reviews)
Room was excellent, hotel was lovely and location was perfect for exploring the city. Especially enjoyed happy hour in the lounge.

Reviewed on 30 Jun 2026

Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Manhattan
Save 100% on your flight
Price was £1,806, price is now £1,231 per person
£1,231
per person
1 Sept - 8 Sept
found 1 day ago
Return direct flight included
London (LGW) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (2,010 reviews)
Hotel was in a great location on a quiet street by NY standards. Room was a good size and was as per photos on website. Bed was comfortable. Shower was not the best but still ok. The complimentary laundry was also a great bonus. Hotel staff were polite and helpful and check in and out was easy, but unfortunately there was one staff member who found a question an inconvenience to her. Also liked the free cookies but we had to be quick to get some. We would stay here again when visiting NY.

Reviewed on 29 Jun 2026

Town of Southold Town Essential Information

Language
English
Currency
U.S dollars
Closest Airport
MacArthur Airport (ISP)
Top Sights
67 Steps Beach, Orient Point County Park and Orient Beach State Park

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 £664 per night from 30 Jul to 31 Jul
£664
30 Jul - 31 Jul
includes taxes & fees
8.4/10 Very good! (659 reviews)
"The Soundview is one of my favorite hotels in greenport ( favorite) we had an amazing room I never wanted to leave!!"

Reviewed on 20 Jun 2026

Sound View Greenport
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
The price is £174 per night from 15 Jul to 16 Jul
£174
15 Jul - 16 Jul
includes taxes & fees
9.2/10 Wonderful! (337 reviews)
"Good."

Reviewed on 24 Jun 2026

Zey Hotel
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is £339 per night from 13 Jul to 14 Jul
£339
13 Jul - 14 Jul
includes taxes & fees
9.4/10 Exceptional! (291 reviews)
"Incredibly beautiful place and perfectly clean!"

Reviewed on 26 Jun 2026

The Shoals Suites and Slips
See all 513 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Town of Southold Town travel package cost?
Discover the best of Town of Southold Town from as little as £1,208. We offer a great selection of flights, hotels and rental cars to suit every budget. You can pick up even better deals when you add a few sightseeing activities to your package.
If I'm not able to travel, can I cancel my Town of Southold Town travel package?
We totally understand that the universe can throw the odd curveball. If you've locked in a Town of Southold Town travel package and need to cancel or amend it, we're here to help. It's always worth having a look at our Customer Service Portal first for information. But generally, if you've taken out your package within 24 hours, you may be able to cancel or amend your itinerary at no cost. If it's more than 24 hours, your hotel, airline or car rental company may charge a fee.
How do I get a cheap travel package to Town of Southold Town?
Combining your hotel and flight with Expedia won't just save valuable time — it'll save you a tidy sum too. A Town of Southold Town holiday package makes it a cinch to put together your ideal trip. With more than 550 airlines worldwide to pick from, finding convenient flights that suit your schedule won't be a challenge. In addition to that, we've got over 1,000,000 hotel options globally to pick from. Talk about choice! Whatever your budget, Expedia puts the world within your reach.
Does Expedia offer Book Now, Pay Later Town of Southold Town holidays?
Expedia has teamed up with online lender Klarna to make booking your next trip easier on your bank balance. Paying by instalment means you can spread the costs of your next big holiday, leaving you with more cash to spend while you're away. Klarna has several payment plans to pick from, so you're sure to find something that fits your budget. Consider these flexible payment options:

  • Pay monthly holidays: Make your holiday dreams a reality sooner with Klarna's convenient monthly instalment plans. If paying bite-sized amounts each month sounds right for you, pick this option during the checkout process.
  • Pay in instalments holidays: If you want to pay off your escape across multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Hitting the "book now" button is much easier with this option. Just put down a small deposit on your escape and then start working on your travel plans.

Where should I stay in Town of Southold Town?
Stay close to the action. Many visitors favor hotels in the vicinity of popular attractions, such as Pindar Vineyards, Raphael Winery and Sparkling Pointe.
What are the top hotels in Town of Southold Town?
Get your trip off to a fantastic start by reserving a room at Hyatt Regency Long Island. It's one of most popular hotels in Town of Southold Town. Another option is Holiday Inn Express Hauppauge, an IHG Hotel.
How far in advance should I book my Town of Southold Town holiday?
Browse Expedia to compare flights as soon as possible. In many cases, you can purchase a seat up to 12 months before departure. If you don't see your preferred carrier, or you're booking late, fear not. Cheap fares to Town of Southold Town sometimes emerge a few weeks before the date of departure.
What does an Expedia Town of Southold Town travel package include?
Rental cars, hotels and flights, or any combination of them — it's your choice. Whether you're headed to Town of Southold Town with the entire family or travelling by yourself, there's a bundle to fit every style and budget. Once you've made your booking, why not add on a few activities?
What should I know before booking a Town of Southold Town travel package?
We already have low prices. However, you'll pick up even better deals when you book your hotels, flights and car rentals together. With an Expedia package, you'll always get transparent pricing and loads of choice.
Can I choose my airline with a Town of Southold Town Expedia travel package?
You certainly can. Expedia has access to more than 550 airline partners throughout the world, so select the carrier that's a good fit for your budget and travel needs.

Stay near popular Town of Southold Town attractions

A rocky shoreline with large boulders and a calm sea.

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.
See properties

What to do in Town of Southold Town

Spirits of Mystic: Cocktail Pub Crawl

Spirits of Mystic: Cocktail Pub Crawl

£73
per adult
100% of travellers recommend
Spirits of Mystic: Cocktail Pub Crawl
great fun with friends

Full Day Private Long Island Wine Tours from New York City

£140
per adult
Full Day Private Long Island Wine Tours from New York City
Hamptons Private Day Trip from New York City

Hamptons Private Day Trip from New York City

£965
per traveller
Hamptons Private Day Trip from New York City
See all activities in Town of Southold Town

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.