Southold Trip

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Top Southold Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Life Hotel

The Life Hotel

3.5 out of 5
Manhattan
Save 100% on your flight
per person
16 Aug - 23 Aug
found 1 day ago
Return flight included
Phoenix (PHX) to New York (JFK)
8.4/10 Very Good! (1,007 reviews)
The Life Hotel was a unique boutique hotel that gave you a home feeling. I liked the character of the rooms and it's history. Loved the pictures from the magazines on the walls. The rooms were modern, spacious, quiet and very clean. I was given a steamer to use for my clothes. Worked beautifully. Large TV in the room. The front door person was super helpful and friendly. He assisted with accessibility. I liked the little cafe for a quick bite to eat but it is rather expensive. The hotel was undergoing some construction as they are making a restaurant next to the lobby. It is going to be finished soon they said. Check in and out was fast and efficient. The elevator to the 10th floor was slow and it is small. Not a problem for us. Loved the marble stairs and the small workout room. Last, the filtered water and ice machine came in very handy. I would definitely stay here again.

Reviewed on 25 May 2024

The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Manhattan
per person
16 Aug - 23 Aug
found 1 day ago
Return flight included
Phoenix (PHX) to New York (JFK)
8.8/10 Excellent! (2,398 reviews)
Good Attention and the Breakfast good

Reviewed on 24 May 2024

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
16 Aug - 23 Aug
found 1 day ago
Return flight included
Phoenix (PHX) to New York (JFK)
9.8/10 Exceptional! (1,000 reviews)
Super clean room with a beautiful view and awsome dining options.

Reviewed on 26 May 2024

Hilton Club The Central at 5th New York

Hilton Club The Central at 5th New York

3.5 out of 5
Manhattan
Save 100% on your flight
per person
16 Aug - 23 Aug
found 1 day ago
Return flight included
Phoenix (PHX) to New York (JFK)
9.6/10 Exceptional! (458 reviews)
Huge rooms (for NYC), very clean, great staff, great location Do keep in mind the rooms aren't serviced so you have to manage your own bedding and garbage. Free coffee and watwr though.

Reviewed on 26 May 2024

Hyatt Place New York Midtown South

Hyatt Place New York Midtown South

3.5 out of 5
Manhattan
Save 100% on your flight
per person
16 Aug - 23 Aug
found 1 day ago
Return flight included
Phoenix (PHX) to New York (JFK)
8.8/10 Excellent! (1,127 reviews)
Good location for mid-town/Times Square access

Reviewed on 26 May 2024

Top hotels in Southold

Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook
2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is ₹8,405 per night from 3 Jun to 4 Jun
₹8,405
per night
3 Jun - 4 Jun
7.4/10 Good! (962 reviews)
"It’s dark. Needs some updates. Staff was nice in person but not so friendly over the phone. Issues with key cards not addressed."

Reviewed on 20 May 2024

Quality Inn Old Saybrook - Westbrook
The Shoals Suites and Slips
The Shoals Suites and Slips
3.5 out of 5
61600 Main Rd, Southold, NY
The price is ₹34,775 per night from 9 Jun to 10 Jun
₹34,775
per night
9 Jun - 10 Jun
9.4/10 Exceptional! (78 reviews)
"This place is such a gem!!! Everything was top notch. Felt like luxury! I can’t wait to go back. If you like decor and design- this is top of the line!"

Reviewed on 24 May 2024

The Shoals Suites and Slips
Hilton Garden Inn Riverhead
Hilton Garden Inn Riverhead
3 out of 5
2038 Old Country Rd, Riverhead, NY
Fully refundableReserve now, pay when you stay
The price is ₹11,716 per night from 29 May to 30 May
₹11,716
per night
29 May - 30 May
8.4/10 Very Good! (1,000 reviews)
"Very comfortable and warm feeling"

Reviewed on 19 May 2024

Hilton Garden Inn Riverhead
See all 4,352 properties in Southold
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 Southold holiday package cost?
From just ₹84,905. Yes, you read that correctly. Our Southold packages are a simple way to make your budget go further. Combine your preferred flights, hotels and rental car and explore this popular destination.
How do I get a cheap travel package to Southold?
Search for flights that suit your busy schedule, add a hotel room to your booking and see how much you save with a Southold holiday package. It’s as easy as that! From flights and hotels to tours and rental cars, Expedia makes travelling cheap and easy. And with more than 550 air carriers and 1,000,000 properties worldwide to pick from, you’ll never be short of choice.
How far in advance should I book my Southold holiday?
Smart travellers will likely want to reserve their seats as early as possible. You can usually start comparing international airfares on Expedia up to 12 months before your flight. If you’re late to book, don’t stress. Cheap prices occasionally occur just weeks prior to departure.
What does an Expedia Southold travel package include?
Hotels, flights and car rentals — we bring you the very best deals. All you have to do is figure out your ideal combination. After you’ve made your booking, you can add on the fun stuff like sightseeing activities. Our travel packages make it easy to put together an awesome Southold escape.
What should I know before booking a Southold travel package?
So many places to wander around, so many things to see and do. With a package, you’ll be able to afford more of them. Bundle your hotels, flights and rental cars and see how much you save.
Can I choose my airline with a Southold Expedia holiday package?
Yes — and it’s easy too. Expedia has access to more than 550 partner airlines throughout the world. Our packages give you the freedom to take your pick of available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Southold holiday package?
If your travel plans in Southold have changed, it’s good to know that it is possible to cancel your booking. If you booked in the last 24 hours, you may be able to get a refund. If your booking is older than that, your hotel, airline or car rental company may charge a fee. To learn more, check our Customer Service Portal.

Popular places to visit

Image for Sparkling Pointe

Sparkling Pointe

You can enjoy a tasting or tour at Sparkling Pointe during your travels to Southold. Discover the sunsets and wineries in this family-friendly area.

Sparkling Pointe
Image for Croteaux Vineyards

Croteaux Vineyards

You can enjoy a tasting or tour at Croteaux Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

Croteaux Vineyards
Image for Sannino's Bella Vita Vineyard

Sannino's Bella Vita Vineyard

You can enjoy a tasting or tour at Sannino's Bella Vita Vineyard during your travels to Southold. Wander the beaches or discover the sunsets in this family-friendly area.

Sannino's Bella Vita Vineyard

More trip options

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.