Southold Trips (flight + hotel)

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Top hotels in Southold

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 P4,640 per night from 9 Jun to 10 Jun
P4,640
per night
9 Jun - 10 Jun
7.6/10 Good! (789 reviews)
"Most of these reviews give less than 5 stars because it’s outdated, which it is, but other than that I love my stay. I had no issues. Front desk staff were super friendly. Coffee machine in the room which was nice. Great area and location too, a lot of restaurants in walking distance. They are in ..."

Reviewed on Jun 5, 2024

Pier Blue Inn Old Saybrook - Essex
The Shoals Suites and Slips
The Shoals Suites and Slips
3.5 out of 5
61600 Main Rd, Southold, NY
The price is P21,705 per night from 24 Jun to 25 Jun
P21,705
per night
24 Jun - 25 Jun
9.4/10 Exceptional! (82 reviews)
"Lovely spot. Beautiful rooms and helpful staff. We will come again"

Reviewed on May 31, 2024

The Shoals Suites and Slips
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 P5,941 per night from 11 Jun to 12 Jun
P5,941
per night
11 Jun - 12 Jun
7.4/10 Good! (966 reviews)
"Great hotel for the money, though it's a little off the beaten path (I had no idea where to find Old Saybrook from the hotel location). Still, it was perfect for my needs. They had a nice (free) continental breakfast and the pool area was great."

Reviewed on May 28, 2024

Quality Inn Old Saybrook - Westbrook
See all 4,361 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 vacation package cost?
From just . 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.

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

What to do in Southold

Image for Private Hamptons Tour with Outlet Center Shopping

Private Hamptons Tour with Outlet Center Shopping

P66,336
Per adult
Private Hamptons Tour with Outlet Center Shopping
Image for Mattituck Bike Wine Country and Fruit Orchard Tour

Mattituck Bike Wine Country and Fruit Orchard Tour

P6,805
Per adult
Mattituck Bike Wine Country and Fruit Orchard Tour
Image for From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

P7,745
Per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
See all activities in Southold

More trip options

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