Southold Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Southold Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
OYO Times Square
Manhattan
$831
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Nashville (BNA) 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 Broadway and Times Square are located nearby.
Oh boy where do I start, when I first checked in there were only four people in front of me, the four of us were wet from the storm ,but for some reason it took over 30 minutes to check in , was told the hot water did not work and it’s $100 per night which it did not say on the website and they don’t tell you until you get to the hotel so they were holding 300 dollars of my money and the AC was not working right, there’s no fan in the bathroom so it was pretty much humid in there. upon my stay, there were people slamming doors from the morning till after midnight., housekeepers were talking very loud in the morning, which is unprofessional. The rooms are below basic, overpriced, and dirty.
Reviewed on Sep 1, 2026
Hotel Riu Plaza Manhattan Times Square
Manhattan
$1,381
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Nashville (BNA) 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.
The Ridge Hotel
Manhattan
$947
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Nashville (BNA) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, a rooftop terrace, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brooklyn Bridge and Wall Street are located nearby.
Property is right next to a club or bar and on a main street. It was very loud all night with music, people on the street , horns honking, and police. The room is very small, barely fits the bed but the bed was comfortable. In NY I expect smaller rooms so there is only so much to say about that but the noise from the are and street all night were too much. I would not be able to ever stay their again due to the noise. If you stay here plan on not sleeping.
Good stuff to say. It had a great location in the city, the 7th floor roof access has a great view, the bed was comfortable, the water gets very hot but does have low pressure.
Reviewed on Sep 1, 2026
Millennium Hotel Broadway Times Square
Manhattan
$993
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Nashville (BNA) to New York (JFK)
Book a stay at this business-friendly hotel in New York. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Times Square and Broadway are located nearby.
Great location...downstairs lobby was in repairs/renovations. Rooms are a bit dated but will be revamped in the near future. Amazing views of Times Square from the 50th floor. Helpfull staff made everything better.
Reviewed on Sep 1, 2026
Ink 48 Hotel
Manhattan
$990
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Nashville (BNA) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Manhattan Cruise Terminal and Broadway are located nearby.
The Gotham Hotel
Manhattan
$1,104
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Nashville (BNA) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grand Central Terminal and Rockefeller Center are located nearby.
Long time to check in
Reviewed on Sep 1, 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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
The Hampton Maid
259 E Montauk Hwy Hampton Bays NY
Stay at this motel in Hampton Bays. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
Hampton's Vacation Inn
177 West Montauk Highway Hampton Bays NY
Stay at this guesthouse in Hampton Bays. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Regal UA Hampton Bays and Good Ground Park are ...
North Fork Resort
690 Queen St Greenport NY
Stay at this cottage in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...
The Chequit
23 Grand Ave Shelter Island Heights NY
Stay at this hotel in Shelter Island Heights. Enjoy free WiFi, free parking, and premium bedding. Popular attractions Shelter Island Country Club and Sunset ...
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 ...
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 ...
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, Oct 22 - Sun, Nov 8
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$145
Roundtrip
found 2 days ago
Tue, Oct 6 - Sat, Oct 10
FLL
Fort Lauderdale - Hollywood Intl.
LGA
LaGuardia
$209
Roundtrip
found 16 hours ago
Tue, Sep 22 - Sat, Oct 3
FLL
Fort Lauderdale - Hollywood Intl.
JFK
John F. Kennedy Intl.
$210
Roundtrip
found 2 days ago
Wed, Dec 2 - Fri, Dec 11
MCO
Orlando Intl.
LGA
LaGuardia
$213
Roundtrip
found 6 days ago
Tue, Nov 10 - Tue, Nov 17
MIA
Miami Intl.
JFK
John F. Kennedy Intl.
$229
Roundtrip
found 5 days ago
Best points of interest in Southold
- Sparkling Pointe Vacations
- Croteaux Vineyards Vacations
- Sannino's Bella Vita Vineyard Vacations
- Horton Point Park Vacations
- McCabe's Beach Vacations
- Corey Creek Winery Vacations
- Osprey's Dominion Vacations
- Mattebella Vineyards Vacations
- The Old Field Vineyards Vacations
- Custer Institute and Observatory Vacations
More AARP Member Vacation Packages
- Las Vegas Vacations
- New York Vacations
- Orlando Vacations
- Los Angeles Vacations
- Miami Vacations
- San Francisco Vacations
- New Orleans Vacations
- Chicago Vacations
- Fort Lauderdale Vacations
- Boston Vacations
- Honolulu Vacations
- San Diego Vacations
- Washington Vacations
- Toronto Vacations
- Anaheim Vacations
- Atlanta Vacations
- Nashville Vacations
- Seattle Vacations
- Phoenix Vacations
- Myrtle Beach Vacations
- Vancouver Vacations
- Palm Springs Vacations
- Denver Vacations
- Tampa Vacations
- Niagara Falls Vacations
- San Antonio Vacations
- Atlantic City Vacations
- Philadelphia Vacations
- Austin Vacations
- Dallas Vacations