Southold Holidays

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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 Rp1.203.881 per night from 23 Sep to 24 Sep
Rp1.203.881
per night
23 Sep - 24 Sep
7.6/10 Good! (850 reviews)
"Although the motel is a bit old, it was charming, and the people there were very nice. I love the location and it was quiet and clean."

Reviewed on 13 Sep 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 Rp3.690.734 per night from 6 Oct to 7 Oct
Rp3.690.734
per night
6 Oct - 7 Oct
9.4/10 Exceptional! (111 reviews)
"Super nice, clean and big room. Beautiful setting, nice staff and easy parking. Breakfast was nothing special, however and the muffins were not so hot. Overall, a great stay!"

Reviewed on 15 Sep 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 Rp1.328.841 per night from 14 Oct to 15 Oct
Rp1.328.841
per night
14 Oct - 15 Oct
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 14 Sep 2024

Quality Inn Old Saybrook - Westbrook
See all 4,325 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 . 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 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
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

What to do in Southold

Image for Long Island Wine and Food Day Trip with Sommelier host from NYC

Long Island Wine and Food Day Trip with Sommelier host from NYC

Rp2.302.795
Per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Image for Private Guided Wine Country Bike Tour in Mattituck

Private Guided Wine Country Bike Tour in Mattituck

Rp3.075.545
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)

Rp12.518.550
Per adult
Private Guided Wine Country Bike Tour For Two (Mattituck)
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.