Southold Vacations

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Find the Best Southold Vacation Packages

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 NT$11,048 per night from Aug 3 to Aug 4
NT$11,048
NT$13,365 total
Aug 3 - Aug 4
includes taxes & fees
9.4/10 Exceptional! (186 reviews)
"Would stay again. So beautiful and clean."

Reviewed on 2025/7/27

The Shoals Suites and Slips
Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25, Southold, NY
10/10 Exceptional! (8 reviews)
"Beautiful house and trip to stay in the North Fork. Hosts are incredible. Highly recommend!!"

Reviewed on 2025/7/23

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Vine & Sand
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 NT$3,284 per night from Aug 10 to Aug 11
NT$3,284
NT$3,776 total
Aug 10 - Aug 11
includes taxes & fees
7.6/10 Good! (1,000 reviews)
"This hotel is modern and provides as close to a full breakfast as you could get under the heading of "continental". The room was spacious and clean. My one complain was the overall design of the building. First, like us, everyone had to drive around both sides of the building to find the office which ..."

Reviewed on 2025/7/27

Quality Inn Old Saybrook - Westbrook
See all 4,353 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.

Discover the most popular places to visit in Southold

Cleanest, prettiest winery on the east end of Long Island! Try the Cuvee' Rose!

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

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

Osprey's Dominion

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

Osprey's Dominion

Frequently asked questions

How much does a Southold vacation package cost?
You can snap up a vacation package to this top destination on Expedia. However, how much your vacation 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 vacation 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 vacation 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 vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and hotels individually. Better still, you can personalize 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 vacation package to Southold?
If you're planning a spur-of-the-moment Southold vacation, 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 favorite 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 accommodations 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 customized Southold vacation package.

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