Town of Southold Town Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £335 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

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

FlightsFlightsHotelsHotels

Southold

Southold

Top Town of Southold Town Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Liberty View Brooklyn hotel

Liberty View Brooklyn hotel

2.5 out of 5
Price was £1,868, price is now £819 per person
£819
per person
23 Mar - 27 Mar
found 1 day ago
Return flight included
London (LON) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
It was very pleasant to stay at the Liberty View Hotel

Reviewed on 13 Feb 2026

Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Price was £1,911, price is now £822 per person
£822
per person
17 Mar - 20 Mar
found 19 hours ago
Return flight included
London (LHR) to Newark Liberty Intl. Airport (EWR)
8/10 Very Good! (2,257 reviews)
The staff was very nice and accommodating. Room was but fine and typical of NYC hotels. Clean, comfy bed, reasonably firm as opposed to those awful, squishy pillow top in so many hotels. Had 3 of the best night’s sleep in a while. My room was a little warm so I had to continually run the a/c in February or prop open the balcony door but that’s just my comfort level. Having the tiny balcony was what sold me on it so I could smoke without going downstairs and outside. I’ll definitely stay here again! Thank you to the staff especially David.

Reviewed on 13 Feb 2026

Best Western Brooklyn-Coney Island Inn

Best Western Brooklyn-Coney Island Inn

2.5 out of 5
Price was £1,916, price is now £828 per person
£828
per person
23 Mar - 27 Mar
found 1 day ago
Return flight included
London (LON) to New York (JFK)
8.8/10 Excellent! (1,002 reviews)
Clean the staff is amazing and very professional.

Reviewed on 14 Feb 2026

Pointe Plaza Hotel

Pointe Plaza Hotel

3 out of 5
Price was £1,921, price is now £835 per person
£835
per person
23 Mar - 27 Mar
found 1 day ago
Return flight included
London (LON) to New York (JFK)
7.8/10 Good! (1,001 reviews)
The room was in fine condition, it could just use some touch ups here and there, and better insulation around the window. Staff was otherwise very courteous and helpful.

Reviewed on 5 Dec 2025

Crowne Plaza HY36 Midtown Manhattan by IHG

Crowne Plaza HY36 Midtown Manhattan by IHG

4 out of 5
Manhattan
Price was £1,895, price is now £833 per person
£833
per person
18 Mar - 21 Mar
found 19 hours ago
Return flight included
London (LHR) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (1,979 reviews)
Room was very clean ! They staff was great customer service representative Ray provide Amazing customer service advising me off the rewards for loyalty members. I wish would paid attention to the fact there’s a resort fee. Don’t be surprised at check-out.

Reviewed on 7 Feb 2026

The Annual Holiday Sale

Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save.
Book now

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 £145 per night from 17 Mar to 18 Mar
£145
17 Mar - 18 Mar
includes taxes & fees
8.4/10 Very Good! (610 reviews)
This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...

Reviewed on 10 Jan 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 £126 per night from 17 Feb to 18 Feb
£126
17 Feb - 18 Feb
includes taxes & fees
8.8/10 Excellent! (566 reviews)
Lovely hotel with great location in town. Great free breakfast and wonderful staff. We will return!

Reviewed on 6 Feb 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 £130 per night from 22 Feb to 23 Feb
£130
22 Feb - 23 Feb
includes taxes & fees
9.4/10 Exceptional! (239 reviews)
Room was great. Clean and comfortable. Glad I found this place and will be back.

Reviewed on 22 Jan 2026

The Shoals Suites and Slips
See all 533 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 £819. 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.

* 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.