Southold Vacations
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Southold Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
YOTEL New York Times Square, Select by Hilton
Manhattan
$1,379
per person
Nov 24 - Nov 29
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Book a stay at this boutique 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 Times Square and Broadway are located nearby.
Unfortunately this was the worst hotel I’ve ever stayed at in New York and bottom 5 anywhere. I will never stay at a Yotel anywhere ever again.
- check in is at 3pm, no exceptions
- check in is supposed to be on a touch screen kiosk that wasn’t working for everyone was checking in at the same time at 3pm and we stood in line for 58 minutes
- The staff were all incredibly rude and unprofessional when you’d ask questions or for help, they answered as if I should know the answer to “where is the restroom?”, “do y’all have a restaurant on property”, and “Can y’all keep my luggage while I explore the city until check-in”
- You have to PAY THEM in CASH ONLY for them to hold your luggage ahead of check in or after check out time… after I’ve already paid for my room, I now have to pay you in cash to hold my bag in a hallway?
- The rooms look like hospital rooms
- Everything is in poor condition or scraped up or damaged in the room
- This is rated a 4 Star Property but it could barely hang on as a 3 Star
- The Bathroom on the 4th floor (public restroom for guests next to their on site property) was DISGUSTING. It was not clean at all. It was 2pm in the afternoon, so not like it was dirty from a bunch of people during a rush hour
- The AC in the room didn’t work, I called down to the desk to make them aware, their exact response was “well we’re fully booked so I can’t move you to a new room or anything.” I said “okay. Thats fine. Just an FYI then” and he replied “thanks.” & hung up
Reviewed on Oct 16, 2026
INNSiDE by Meliá New York Nomad
Manhattan
$2,070
per person
Dec 23 - Dec 28
found 18 hours ago
Roundtrip non-stop flight included
Sacramento (SMF) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Madison Square Garden and Bryant Park are located nearby.
Hotel Riu Plaza New York Times Square
Manhattan
$2,465
per person
Dec 23 - Dec 28
found 18 hours ago
Roundtrip non-stop flight included
Sacramento (SMF) 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.
Great location. The hotel had everything we needed and the bathroom was well appoiinted
Reviewed on Oct 16, 2026
Hotel Riu Plaza Manhattan Times Square
Manhattan
$2,312
per person
Dec 23 - Dec 28
found 18 hours ago
Roundtrip non-stop flight included
Sacramento (SMF) 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.
10/10
Reviewed on Oct 16, 2026
Margaritaville Resort Times Square
Manhattan
$1,543
per person
Nov 24 - Nov 29
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Stay at this hotel in New York. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Times Square and Bryant Park are located nearby.
Ace Hotel New York
Manhattan
$1,819
per person
Dec 23 - Dec 28
found 18 hours ago
Roundtrip non-stop flight included
Sacramento (SMF) 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.
Such a great location to stay.
Reviewed on Oct 16, 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 ...
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 ...
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 ...
Quality Inn Old Saybrook - Westbrook
100 Essex Rd Old Saybrook CT
Book a stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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 ...
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 ...
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 ...
Shorewood Inn
1399 Main Rd Riverhead NY
Stay at this motel in Riverhead. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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 ...
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.
$168
Roundtrip
found 1 day ago
Wed, Dec 2 - Wed, Dec 9
MCO
Orlando Intl.
LGA
LaGuardia
$188
Roundtrip
found 5 days ago
Sat, Dec 5 - Tue, Dec 8
FLL
Fort Lauderdale - Hollywood Intl.
LGA
LaGuardia
$199
Roundtrip
found 1 hour ago
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
JFK
John F. Kennedy Intl.
$199
Roundtrip
found 19 hours ago
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
EWR
Newark Liberty Intl. Airport
$199
Roundtrip
found 14 hours 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
- Mattebella Vineyards Vacations
- Corey Creek Winery Vacations
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