Southold Vacations from ￥448,105

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The Latest Southold Vacation Packages

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

Hotel Beacon

4 out of 5
Manhattan
Price was ￥640,978, price is now ￥448,105 per person
￥448,105
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
9.4/10 Exceptional! (1,490 reviews)
Room was always clean and staff was helpful.

Reviewed on Jul 6, 2026

5th & 55th Residence Club

5th & 55th Residence Club

5 out of 5
Manhattan
Save 100% on your flight
Price was ￥1,737,597, price is now ￥1,104,998 per person
￥1,104,998
per person
Sep 19 - Sep 26
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.4/10 Very Good! (5 reviews)

The High Line Hotel

The High Line Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was ￥793,356, price is now ￥546,458 per person
￥546,458
per person
Sep 19 - Sep 26
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.6/10 Excellent! (1,006 reviews)
The central air in Room 56 was not working, & someone put in a window air conditioner. The room was 75 degrees because heat was coming in from the side of the window unit. It was over 100degrees on July 4th. Luckily we were able to change rooms and Room 22 was nice & cool. The staff is lovely!

Reviewed on Jul 9, 2026

Hotel Hendricks

Hotel Hendricks

4 out of 5
Manhattan
Price was ￥717,900, price is now ￥512,816 per person
￥512,816
per person
Sep 19 - Sep 26
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.6/10 Excellent! (1,743 reviews)
Decent, nothing crazy. Bathroom is meh

Reviewed on Jul 9, 2026

Hilton Garden Inn New York/Manhattan-Midtown East

Hilton Garden Inn New York/Manhattan-Midtown East

3.5 out of 5
Manhattan
Save 100% on your flight
Price was ￥833,879, price is now ￥596,768 per person
￥596,768
per person
Sep 19 - Sep 26
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
7.8/10 Good! (1,738 reviews)
The room was clean and well air conditioned. Staff is friendly. They are going through some construction in the lobby but it wasn't an issue.

Reviewed on Jul 10, 2026

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 ￥60,364 per night from Jul 26 to Jul 27
￥60,364
￥73,026 total
Jul 26 - Jul 27
includes taxes & fees
9.4/10 Exceptional! (292 reviews)
"Had an amazing stay here during the off season with our newborn. The room was clean and grounds were beautifully maintained. Can’t wait to come back here this summer to see the property in full action."

Reviewed on Jul 8, 2026

The Shoals Suites and Slips
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is ￥13,905 per night from Jul 12 to Jul 13
￥13,905
￥15,991 total
Jul 12 - Jul 13
includes taxes & fees
8/10 Very Good! (1,013 reviews)
"The room was hot, and AC barely worked."

Reviewed on Jul 10, 2026

Pier Blue Inn Old Saybrook - Essex
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
8.4/10 Very Good! (664 reviews)
"The staff was helpful and nice. The exterior of the property was fine and the landscaping pretty. However the room was awful - not particularly clean, a noisy, wall ac plugged in next to the bed, felt like a renovated motel room. Sorry not worth $700/ night."

Reviewed on Jul 8, 2026

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Sound View Greenport
See all 4,358 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.

Stay near popular Southold attractions

Sparkling Pointe

8.8/10 (11 reviews)
Sparkling Pointe crafts exquisite sparkling wines using traditional Méthode Champenoise in their Southold vineyard. Savor their diverse bubblies in an elegant tasting room with vineyard views.
See properties

What to do in Southold

great fun with friends

Full Day Private Long Island Wine Tours from New York City

￥30,231
per adult
Full Day Private Long Island Wine Tours from New York City
The Hamptons Coastal Escape from NYC

The Hamptons Coastal Escape from NYC

￥150,093
per traveler
The Hamptons Coastal Escape from NYC
See all activities in Southold

Frequently asked questions

How much does a Southold vacation package cost?
You can snap up a vacation package to this top destination from ￥448,105 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.

Explore a world of travel with Expedia

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