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
The price is Rp1.423.911 per night from 23 May to 24 May
Rp1.423.911
per night
23 May - 24 May
7.6/10 Good! (780 reviews)
Nice hotel
"This is a no-frills hotel. However we had a mini fridge, microwave and coffee maker in our room. VERY spacious. Staff were friendly and at the front desk when we needed them to be there. A lady came to our door once to see if we needed fresh towels (we were there for 6 days). We will stay here on ..."

Reviewed on 16 May 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 Rp4.719.705 per night from 23 May to 24 May
Rp4.719.705
per night
23 May - 24 May
9.4/10 Exceptional! (76 reviews)
Great place
"great room, great size, clean, nice.....just not a fan of the weighted blankets on the beds!"

Reviewed on 19 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 Rp2.267.917 per night from 28 May to 29 May
Rp2.267.917
per night
28 May - 29 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 4,348 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 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 Half Day Private Long Island Wine Tour Experience

Half Day Private Long Island Wine Tour Experience

Rp4.172.848
Per adult
Half Day Private Long Island Wine Tour Experience
Image for Long Island Full Day Wine and Food Tasting Vineyard Tour from NYC

Long Island Full Day Wine and Food Tasting Vineyard Tour from NYC

Rp2.381.302
Per adult
Long Island Full Day Wine and Food Tasting Vineyard Tour from NYC
Image for Private Hamptons Tour with Outlet Center Shopping

Private Hamptons Tour with Outlet Center Shopping

Rp18.540.136
Per adult
Private Hamptons Tour with Outlet Center Shopping
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.