Deals on vacations and trips to Southold

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Southold flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Log Comfort 3

Log Comfort 3

3 out of 5
Lower Vailsburg
Save 100% on your flight
Price was $1,070, price is now $614 per person
$614
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Free WiFi in public areas is available at this apartment. Take advantage of the self parking.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $5,098, price is now $2,727 per person
$2,727
per person
Dec 1 - Dec 7
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
A full-service spa, a gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the seasonal outdoor pool and visit the 2 bars/lounges and poolside bar for drinks.
Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
Price was $3,154, price is now $1,737 per person
$1,737
per person
Dec 2 - Dec 7
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
A private beach and a restaurant are featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like continental breakfast and WiFi in public areas.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was $1,348, price is now $788 per person
$788
per person
Dec 14 - Dec 17
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free buffet breakfast each morning.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was $1,204, price is now $716 per person
$716
per person
Dec 14 - Dec 17
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. A snack bar/deli, dry cleaning, and luggage storage are also on offer.

Top Southold hotels deals

The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
$254 nightly
The price is $286 total per night
$286 total
Oct 1 - Oct 2
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. A business center, a communal living room, and a picnic area are also on offer.
Free WiFi
Restaurant
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Free Cancellation
$78 nightly
The price is $90 total per night
$90 total
Sep 29 - Sep 30
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A picnic area is also provided.
Pet friendly
Parking included
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Free Cancellation
Reserve now, pay when you stay
$218 nightly
The price is $251 total per night
$251 total
Oct 4 - Oct 5
Total with taxes and fees
This smoke-free resort features a private beach, a full-service spa, and 3 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Enjoy the 2 outdoor tennis courts and perks like free valet parking and free WiFi.
On private beach
Pool
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$248 nightly
The price is $283 total per night
$283 total
Oct 26 - Oct 27
Total with taxes and fees
A private beach and a restaurant are featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like continental breakfast and WiFi in public areas.
On private beach
Pool
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
$111 nightly
The price is $127 total per night
$127 total
Oct 28 - Oct 29
Total with taxes and fees
This hotel's 2 outdoor tennis courts and outdoor pool are among the featured amenities. Guests will appreciate free perks like free self parking and WiFi in public areas. Free parking, free newspapers, and barbecue grills are also on offer.
Pool
Pet friendly
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
$169 nightly
The price is $193 total per night
$193 total
Oct 12 - Oct 13
Total with taxes and fees
A bar/lounge and a coffee shop are featured at this hotel, along with free self parking. WiFi in public areas is free. A terrace, a garden, and a picnic area are also on offer.
Pet friendly
Parking included
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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)
You can enjoy a tasting or tour at Sparkling Pointe during your travels to Southold. Discover the sunsets and wineries in this family-friendly area.
See properties

Frequently asked questions

How much are vacation packages to Southold?
With a Travelocity vacation package, you could paint the town red in Southold for only $614. Activities, flights and hotels — we've got you. You'll save loads just by bundling together your bookings. And with all of that taken care of before you even set off, you don't have to worry about a thing.
Where can I get the best vacation package deals for Southold?
No matter what you enjoy doing, Travelocity can help you score the perfect Southold package deal. All you have to do is mix and match from our 400 air carriers and 1,000,000 properties around the world.
Why should I purchase my Southold vacation bundle with Travelocity?
Because life is one incredible journey, and we offer everything you could hope for to help you along the way. With our top-quality service and Price Match Guarantee, you can book with confidence. Plus, you can sleep easy while you're on the road knowing you can reach us with our 24/7 support.
Can I save on my Southold car rental if I book it with a hotel or flight?
You can with our Southold vacation packages. With one of these, there are tons of ways to stretch your travel budget further. Combine any two or more car, hotel, flight and tour bookings and watch your savings start to grow. With your own set of wheels, all the popular attractions around Southold are an unforgettable road trip away.

Photos of local treasures

Browse Southold vacation photos for more inspiration

A calm lake with a forest in the background during sunset.
A calm lake with tall grasses in the foreground and a forested shoreline under a pink sky.
A river with red vegetation and a forest in the background.
A lifeguard tower, a boat, and a sandy beach with the ocean in the background.
A river with boats, a marina, and residential areas.