Southold Vacation Packages

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Your Southold Vacation

The coastal scenery and rich history are just the beginning of the things Southold has going for it. Experience the very best of this interesting city your way with a customized Southold vacation package. 67 Steps Beach, Raphael Winery and Railroad Museum of Long Island are just some of the many sights worth checking out during your trip to Southold. A few quick clicks is all it takes to put together your ideal Southold vacation on Expedia.

Top Southold Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Somerset Hills Hotel, Tapestry Collection by Hilton

Somerset Hills Hotel, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
per person
Oct. 26 - Oct. 31
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (NYC)
8.8/10 Excellent! (153 reviews)
Great location , super convenient. I have to say that Cesar is an excellent employee. He did above and beyond with his services. Super helpful and knowledgeable.

Reviewed on Sep. 21, 2024

Newark Liberty International Airport Marriott

Newark Liberty International Airport Marriott

4 out of 5
Save 100% on your flight
per person
Oct. 31 - Nov. 4
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (1,000 reviews)
Room service has to be done via QR code to Web page then enter several other info that's easy too much work. Should be able to do this through TV.

Reviewed on Sep. 12, 2024

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
Nov. 7 - Nov. 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (1,007 reviews)
Excellent view from the rooftop bar.

Reviewed on Sep. 18, 2024

Newark Hansbury Multi Level House

Newark Hansbury Multi Level House

2 out of 5
Weequahic
Save 100% on your flight
per person
Oct. 26 - Oct. 31
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newark Liberty Intl. Airport (EWR)
6/10 (3 reviews)
Park Lane New York

Park Lane New York

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Nov. 14 - Nov. 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (1,075 reviews)
Location is great. Would have liked extra chair in room, and coffee maker.

Reviewed on Sep. 22, 2024

Ready to book your vacation to Southold?

 

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Southold Hotel Deals

The Shoals Suites and Slips
The Shoals Suites and Slips
3.5 out of 5
61600 Main Rd, Southold, NY
The price is CA $327 per night from Oct. 10 to Oct. 11
CA $327
CA $406 total
includes taxes & fees
Oct 10 - Oct 11
9.4/10 Exceptional! (114 reviews)
"The shoals property was interesting.. we almost drove past it because I thought it was a marina… which is actually on the property of the hotel. Very nice outdoor space to sit and relax and watch the boats come and go. Corn hole and other games on the lawn and a cute food truck and outdoor bar. Live ..."

Reviewed on Sep. 21, 2024

The Shoals Suites and Slips
Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is CA $97 per night from Sep. 29 to Sep. 30
CA $97
CA $112 total
includes taxes & fees
Sep 29 - Sep 30
7.6/10 Good! (855 reviews)
"Very helpful, real people! Many dinning options within two minutes."

Reviewed on Sep. 23, 2024

Pier Blue Inn Old Saybrook - Essex
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 CA $128 per night from Oct. 9 to Oct. 10
CA $128
CA $148 total
includes taxes & fees
Oct 9 - Oct 10
7.4/10 Good! (1,001 reviews)
"I stayed a Friday night. The property looks rundown from the outside but is better inside. Rooms have good ventilation and air control, and they are very clean. Breakfast is included and is excellent. Nearby dining options are outstanding"

Reviewed on Sep. 14, 2024

Quality Inn Old Saybrook - Westbrook
See all 4,321 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Southold vacation package cost?
From just CA $766. 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 vacation package. It’s as easy as that! From flights and hotels to tours and rental cars, Expedia makes traveling 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 vacation?
Smart travelers 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 vacation 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 vacation 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.

Discover the most popular places to visit in Southold

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

What to do in Southold

Image for Private Guided Wine Country Bike Tour in Mattituck

Private Guided Wine Country Bike Tour in Mattituck

CA $270
Per adult
Private Guided Wine Country Bike Tour in Mattituck
Image for Private Guided Wine Country Bike Tour For Two (Mattituck)

Private Guided Wine Country Bike Tour For Two (Mattituck)

CA $1,098
Per adult
Private Guided Wine Country Bike Tour For Two (Mattituck)
Image for Mattituck Bike Wine Country and Fruit Orchard Tour

Mattituck Bike Wine Country and Fruit Orchard Tour

CA $171
Per adult
Mattituck Bike Wine Country and Fruit Orchard Tour
See all activities in Southold

Other vacations you might like

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