Southold Vacations
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Southold Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel St. James
Manhattan
$931
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Times Square and Broadway are located nearby.
Honestly, the perfect place to stay if you plan on having fun in the city, enjoying Broadway shows, and really just want a clean and comfortable place to sleep. The location can’t be beat, though I would definitely request a higher floor room. Second floor, and you hear alllll the road noise, and it is considerable. There are no amenities, except for the most basic (soap, shampoo, body wash, two plastic cups, a hair dryer). Wish there was a bottled water option, but the bed was comfortable, the room was impeccably spotless, and for the price, it was perfect for us.
Reviewed on Oct 26, 2026
Hotel Riu Plaza Manhattan Times Square
Manhattan
$1,212
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Broadway and Rockefeller Center are located nearby.
Room was small but clean and we had a clear view of Time Square and other historic buildings.
Reviewed on Oct 26, 2026
Hotel Riu Plaza New York Times Square
Manhattan
$1,369
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New York (JFK)
Book a stay at this business-friendly hotel in New York. Enjoy free breakfast, a fitness center, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Broadway and Times Square are located nearby.
Very nice and clean hotel. The staff were friendly.
Reviewed on Oct 26, 2026
Hotel Beacon
Manhattan
$1,801
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Fort Myers (RSW) to New York (JFK)
Book a stay at this business-friendly hotel in New York. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lincoln Center and Central Park are located nearby.
The hotel’s location is great, but the property is in need of renovations! The room was clean, but it had a strange smell. The beds were comfortable, and the staff was extremely friendly and helpful. Felt safe and had a supermarket just across the street.
The room was spacious and convenient, especially since I was traveling with my three kids.
Overall, the location and staff were definite highlights, but the hotel could really benefit from some much-needed updates.
Reviewed on Oct 25, 2026
The William Hotel Midtown, New York
Manhattan
$2,222
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Fort Myers (RSW) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Popular attractions Bryant Park and Grand Central Terminal are located nearby.
Great location! Clean and super kind and helpful staff.
Reviewed on Oct 26, 2026
Ace Hotel New York
Manhattan
$940
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, 2 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Madison Square Garden and Bryant Park are located nearby.
We loved this hotel. The room was a bit cramped, but since we barely in it, it wasn’t an issue. The shower didn’t drain well, and the water pressure was REALLY strong. When I showered, there was a bit of a pool in the shower. Other than that, we didn’t have any problems.
The staff were extremely helpful and kind with whatever we needed.
The hotel was conveniently located near MSG and Macy’s. Would stay here again!
Reviewed on Oct 24, 2026
Southold Vacation Packages
Looking to save both time and money on your upcoming holiday to Southold? The AARP Travel Center Powered by Expedia® can help you do both. We're here to book everything you'll need to make your Southold trip one to remember. Our Travel Center is a one-stop shop where you can put together the best vacation package for you. AARP Travel Center has an incredible choice of flights and hotels, as well as local things to do to select from.
Southold Hotel Deals
Our listings include hotels that are close to all the Southold points of interest, and some that are just outside the city center for a quieter retreat.
We have fantastic rates on everything from all-inclusive resorts that satisfy all the vacation must-haves to inexpensive accommodations perfect for those on a budget. You can scan all the options and select the hotel that is perfect for you. With AARP Travel Center's Southold hotel packages, you not only get a great rate on your flight, but also a terrific place to stay.
Things to do in Southold
Southold has around 22,274 people that make this city their home. If you wanted to take a break from the hustle and bustle of a big city, then you are in the right spot. The city's art district is draw for many tourist and locals.
Looking for more? Then Check out AARP Travel Center's "Things to Do" Page.
Package Your Southold Vacation and Save
As an AARP Member, you can benefit from all the great deals. You'll save on select hotels worldwide, flights, and even rental cars. No matter what vacation package you choose, your membership savings helps you get a great deal. So what are you waiting for? Bundle now and get ready for your Southold vacation.
Top Hotel Deals
The Shoals Suites and Slips
61600 Main Rd Southold NY
Stay at this hotel in Southold. Enjoy free WiFi, free bicycles on site, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions ...
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
The Atlantic Hotel
1655 County Road 39 Southampton NY
Stay at this hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
Sound View Greenport
58775 County Rd 48 Greenport NY
Book a stay at this beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Zey Hotel
439 Main Street Greenport NY
Book a stay at this boutique hotel in Greenport. Enjoy free parking, free bicycles on site, and daily housekeeping. Popular attractions Greenport Harbor Brewing ...
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
Book a stay at this business-friendly hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
Greenview Inn Riverhead
1433 W Main St Riverhead NY
Stay at this motel in Riverhead. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Riverhead Raceway and Out East Family Fun are located ...
Saybrook Point Resort & Marina
2 Bridge St Old Saybrook CT
Book a stay at this spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in ...
Faraway Sag Harbor
31 West Water Street Sag Harbor NY
Stay at this hotel in Sag Harbor. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
Hyatt Place Long Island East End
451 East Main Street Riverhead NY
Book a stay at this business-friendly hotel in Riverhead. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Budget Host East End
30 Lake Avenue Riverhead NY
Stay at this motel in Riverhead. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
Hampton Bays Hotel on Main
2 W Montauk Hwy Hampton Bays NY
Stay at this hotel in Hampton Bays. Enjoy free WiFi, 2 bars/lounges, and cable TV channels. Popular attractions Good Ground Park and Meschutt Beach are located ...
Hilton Garden Inn Riverhead
2038 Old Country Rd Riverhead NY
Stay at this hotel in Riverhead. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
The Harbor Front Inn
209 Front St Greenport NY
Book a stay at this business-friendly hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Thu, Dec 3 - Sun, Dec 6
MCO
Orlando Intl.
SWF
Stewart Intl.
$108
Roundtrip
found 5 days ago
Wed, Nov 11 - Mon, Nov 16
MCO
Orlando Intl.
JFK
John F. Kennedy Intl.
$159
Roundtrip
found 1 day ago
Tue, Nov 10 - Mon, Nov 16
MCO
Orlando Intl.
JFK
John F. Kennedy Intl.
$178
Roundtrip
found 1 day ago
Sat, Dec 5 - Tue, Dec 8
MIA
Miami Intl.
LGA
LaGuardia
$199
Roundtrip
found 5 days ago
Sat, Dec 5 - Tue, Dec 8
LAX
Los Angeles Intl.
EWR
Newark Liberty Intl. Airport
$344
Roundtrip
found 5 days ago
Best points of interest in Southold
- Sparkling Pointe Vacations
- Croteaux Vineyards Vacations
- Sannino's Bella Vita Vineyard Vacations
- Osprey's Dominion Vacations
- The Old Field Vineyards Vacations
- Custer Institute and Observatory Vacations
- McCabe's Beach Vacations
- Horton Point Park Vacations
- Corey Creek Winery Vacations
- Mattebella Vineyards Vacations
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