Southold Holidays

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Top Flight + Hotel Deals in Southold

Price found within the past 48 hours. Click for updated prices.
Walker Hotel Tribeca

Walker Hotel Tribeca

3.5 out of 5
Manhattan
Save 100% on your flight
per person
20 Mar - 25 Mar
found 5 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
8.8/10 Excellent! (788 reviews)
The Walker hotel is an amazing property to stay at! The front desk was very helpful and made sure that our stay was comfortable. Only negatives are the room size but it's NYC and the general location. Very close to Canal st but still not a big deal. I highly recommend visiting the Walker hotel.

Reviewed on 10 Jan 2025

The Herald by LuxUrban

The Herald by LuxUrban

2.5 out of 5
Manhattan
Save 100% on your flight
per person
20 Mar - 25 Mar
found 5 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
7.8/10 Good! (312 reviews)
Would recommend property to friends and would definitely book again. Jon who checked us in was very welcoming and accommodating. Thanks for a wonderful stay.

Reviewed on 11 Jan 2025

The Washington by LuxUrban

The Washington by LuxUrban

3 out of 5
Manhattan
Save 100% on your flight
per person
20 Mar - 25 Mar
found 5 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
8.2/10 Very Good! (1,004 reviews)
You get what you can for the price. The place needs minor adjustments. But it is close to the World Trade Center and trains.

Reviewed on 13 Jan 2025

Tuscany by LuxUrban

Tuscany by LuxUrban

3 out of 5
Manhattan
Save 100% on your flight
per person
20 Mar - 25 Mar
found 5 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
8.2/10 Very Good! (1,009 reviews)
The property is in walking distance to Grand Central Station, the room was clean and a very nice size. The front desk staff are amiable and willing to assist. Because it is a hotel in the centers in the city the hotel has limited onsite activities and if you are there to sleep in you may not get maid service as it appear’s as if they only come around once. I enjoyed my stay overall and would return and or recommend.

Reviewed on 13 Jan 2025

The Blakely by LuxUrban

The Blakely by LuxUrban

2.5 out of 5
Manhattan
Save 100% on your flight
per person
2 Apr - 9 Apr
found 1 day ago
Return flight included
Shannon (SNN) to New York (JFK)
7.8/10 Good! (471 reviews)
no frills; big room; fridge and microwave; great location; small hotel

Reviewed on 31 Dec 2024

Top hotels in Southold

The Shoals Suites and Slips
The Shoals Suites and Slips
3.5 out of 5
61600 Main Rd, Southold, NY
The price is €188 per night from 28 Jan to 29 Jan
€188
includes taxes & fees
28 Jan - 29 Jan
9.4/10 Exceptional! (145 reviews)
"I can’t say enough great things about this place. Absolutely wonderful !"

Reviewed on 4 Jan 2025

The Shoals Suites and Slips
Hyatt Place Long Island East End
Hyatt Place Long Island East End
3 out of 5
451 East Main Street, Riverhead, NY
Fully refundableReserve now, pay when you stay
The price is €131 per night from 21 Jan to 22 Jan
€131
includes taxes & fees
21 Jan - 22 Jan
9/10 Wonderful! (1,002 reviews)
"Just Great!"

Reviewed on 8 Jan 2025

Hyatt Place Long Island East End
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 €96 per night from 2 Feb to 3 Feb
€96
includes taxes & fees
2 Feb - 3 Feb
7.4/10 Good! (982 reviews)
"Friendly and helpful staff and the breakfast was good. The only issue was one of the beds in our room (212) literally fell off the frame on one side when sat on.We were tired and had already settled in, so we didn’t request a new room and made it work."

Reviewed on 8 Jan 2025

Quality Inn Old Saybrook - Westbrook
See all 4,251 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?
You can snap up a holiday package to this top destination from €797 on Expedia. However, how much your holiday to Southold costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Southold?
January, February and March are great times to look for cheap Southold holiday packages. Choosing to travel in quieter months means you can generally find better prices on flights and hotels.
How many days is enough for Southold?
Dedicate at least 3 days for your Southold holiday to immerse yourself in everything that makes this place unique. Explore popular areas, including Greenport West and Pipes Cove. Then head to the major sights like Osprey’s Dominion and Croteaux Vineyards. With a good itinerary, you can keep busy with room for some me-time too. Want to travel beyond Southold? Consider an excursion or two.
How to find the best Southold package deals?
Bagging a cheap Southold package deal is a cinch with Expedia. Once you’ve entered your destination and travel dates under our “Packages” tab, set your maximum budget, add some filters and browse what’s available. You can tweak your search by “Popular locations,” “Property type,” “Guest rating” and more. Sort the results by “Price: low to high” to discover the most pocket-friendly Southold package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Southold holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking flights and hotels individually. Better still, you can personalise your Southold escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Southold?
If you’re planning a spur-of-the-moment Southold holiday, check out our last-minute deals that can be booked up to a week before you go. Don’t want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Southold?

  1. Choose your dates: The things you’d like to do in Southold and your favourite season can help you decide when to travel.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and meals to flights and experiences. Your accommodation will likely be the largest expense during your trip to Southold.
  3. Decide how long to go for: Now that you know more about Southold, you can work out the perfect length of your break. Put together a rough itinerary and allocate enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customised Southold holiday package.

Popular places to visit

Corey Creek Winery

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

Corey Creek Winery

Horton Point Park

Explore the great outdoors at Horton Point Park, a lovely green space in Southold. Wander the beaches or discover the sunsets in this family-friendly area.

Horton Point Park

Mattebella Vineyards

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

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