Southold Vacations from $374
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Your Southold Vacation
The coastal scenery and rich history are just the beginning of the things Southold has going for it. Experience the very best of this interesting city your way with a customized Southold vacation package. 67 Steps Beach, Raphael Winery and Railroad Museum of Long Island are just some of the many sights worth checking out during your trip to Southold. A few quick clicks is all it takes to put together your ideal Southold vacation on Expedia.
The Latest Southold vacation packages
Price found within the past 48 hours. Click for updated prices.
Arthouse Hotel New York City
Manhattan
Save 100% on your flight
Price was $643, price is now $374 per person
$374
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (2,013 reviews)
The only thing is the breakfast only includes either a plain crossaint or a bagel
Reviewed on Jul 11, 2026
Night Hotel Broadway
Manhattan
Save 100% on your flight
Price was $1,351, price is now $722 per person
$722
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
7.4/10 Good! (3,239 reviews)
Not quite what I was expecting based on previous reviews. Its true, its very affordable, in a good location for what we needed to do. Staff was accommodating. The first room that they assigned us had such a musty/smoky smell that I had problems breathing. The staff was gracious enough to let us choose another room. The rooms that we saw all had older discolored carpets and peeling wall paper in multiple spots. The beds appeared clean and comfortable. The bathroom was nice enough (some cracks in floor and phone was in the bathroom), however, there was no soap to use to wash hands other than body shampoo from shower. The layout of the hotel rooms that we saw was very unusual, with a lot of nooks and crannies and hotel room doors paired extremely closely together. The only vending machine that we saw was out of order. We weren't familiar with any other amenities other than the two bottles of water that we received on the first day, the TV mounted on the wall and the coffee for the coffee pot. I guess that there is a sports club or gym of something that we get charged an extra $40 for but we unfortunately did not use it.
Reviewed on Jul 12, 2026
Ink 48 Hotel
Manhattan
Save 100% on your flight
Price was $976, price is now $561 per person
$561
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (1,710 reviews)
They don't have enough air-conditioning. The room was HOT and not in a good way.
Reviewed on Jul 12, 2026
Stay near popular Southold attractions
What to do in Southold
Full Day Private Long Island Wine Tours from New York City
$189
per adult
Southold Hotel Deals
The Shoals Suites and Slips
61600 Main Rd Southold NY
$397 nightly
The price is $450 total per night from Jul 26 to Jul 27
$450 total
Jul 26 - Jul 27
Total with taxes and 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
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
$96 nightly
The price is $111 total per night from Jul 13 to Jul 14
$111 total
Jul 13 - Jul 14
Total with taxes and fees
8/10 Very Good! (1,015 reviews)
"Still the same wonderful little place as the last time I stayed here!"
Reviewed on Jul 11, 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
$552 nightly
The price is $630 total per night from Aug 3 to Aug 4
$630 total
Aug 3 - Aug 4
Total with taxes and fees
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
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.
Find the Best Southold Vacation Packages
Southold Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Tweed - New Haven Regional Airport (HVN) |
Population | 5,700 |
Max Temp Winter | 40ºF |
Max Temp Summer | 75ºF |
Top Sights | Wolffer Estates Vineyard, 67 Steps Beach and Macari Vineyards |
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Frequently asked questions
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- Raphael Winery
- Shinnecock Nation Cultural Center and Museum
- Noyac Golf Club
- Mattebella Vineyards
- Pugliese Vineyards
- Cutchogue Vacations
- Visit Sag Harbor
- Elizabeth A. Morton National Wildlife Refuge
- 67 Steps Beach
- Pindar Vineyards
- The Old Field Vineyards
- Sannino's Bella Vita Vineyard
- Norman E. Klipp Marine Park
- Bedell Cellars
- East Hampton Main Beach
- Ponquogue Beach
- Where to stay in Southold
- Shelter Island Vacations
- 8 Hands Farm
- Greenport Vacations
- Longhouse Reserve
- Visit Southampton
- Visit Montauk
- Sunset Beach
- Havens House
- Railroad Museum of Long Island
- Visit Southold
- Peconic Bay Winery
- Kontokosta Winery
- Camera Obscura
- Visit Hampton Bays
- Sylvester Manor
- Visit Shelter Island
- Wolffer Estates Vineyard
- Waters Crest Winery
- Visit Greenport
- Cooper's Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
