Book Exclusive Southold Vacation Packages

Choose one or more items to build your trip:

Southold flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
per person
Jun. 22 - Jun. 26
Roundtrip flight included
Montreal (YUL) to New York (JFK)
Stay at this 5-star luxury hotel in New York. Enjoy free WiFi, breakfast, and a free area shuttle. Popular attractions 5th Avenue and Rockefeller Center are located nearby. Discover genuine guest reviews for The Towers at Lotte New York Palace, in Manhattan neighborhood, along with the latest prices and availability – book now.
The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Jun. 14 - Jun. 16
Roundtrip flight included
Buffalo (BUF) to New York (JFK)
Stay at this 4.5-star luxury hotel in New York. Enjoy breakfast, WiFi, and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Grand Central Terminal and Bryant Park are located nearby. Discover genuine guest reviews for The Westin New York Grand Central, in Manhattan neighborhood, along with the latest prices and availability – book now.
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Jun. 3 - Jun. 7
Roundtrip flight included
Buffalo (BUF) to New York (JFK)
Stay at this spa hotel in New York. Enjoy a full-service spa, breakfast, and WiFi. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions 5th Avenue and Rockefeller Center are located nearby. Discover genuine guest reviews for Lotte New York Palace, in Manhattan neighborhood, along with the latest prices and availability – book now.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Jul. 15 - Jul. 22
Roundtrip flight included
Buffalo (BUF) to New York (JFK)
Stay at this 4-star business-friendly hotel in New York. Enjoy free breakfast, WiFi, and a fitness center. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Broadway and Times Square are located nearby. Discover genuine guest reviews for Hotel Riu Plaza New York Times Square, in Manhattan neighborhood, along with the latest prices and availability – book now.
Park Lane New York

Park Lane New York

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Jun. 2 - Jun. 7
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
Stay at this luxury hotel in New York. Enjoy free WiFi, 2 restaurants, and breakfast. Our guests praise the bar and the helpful staff in our reviews. Popular attractions 5th Avenue and Rockefeller Center are located nearby. Discover genuine guest reviews for Park Lane New York, in Manhattan neighborhood, along with the latest prices and availability – book now.

Top Southold hotels deals

The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd, Southold, NY
The price is CA $354 per night
CA $354
per night
Apr. 28 - Apr. 29
Stay at this 3.5-star hotel in Southold. Enjoy free breakfast, free WiFi, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions The Old Field Vineyards and Crescent Beach are located nearby. Discover genuine guest reviews for The Shoals Suites and Slips along with the latest prices and availability – book now.
Breakfast included
Restaurant
Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

3 out of 5
2038 Old Country Rd, Riverhead, NY
Free cancellation
Reserve now, pay when you stay
The price is CA $150 per night
CA $150
per night
May 2 - May 3
Stay at this 3-star hotel in Riverhead. Enjoy free WiFi, free parking, and breakfast. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Splish Splash Water Park and Tanger Outlet Center are located nearby. Discover genuine guest reviews for Hilton Garden Inn Riverhead along with the latest prices and availability – book now.
Hot tub
Pet-friendly
Residence Inn by Marriott New York Long Island East End

Residence Inn by Marriott New York Long Island East End

3 out of 5
2012 Old Country Road, Riverhead, NY
Free cancellation
Reserve now, pay when you stay
The price is CA $183 per night
CA $183
per night
Apr. 29 - Apr. 30
Stay at this 3-star business-friendly hotel in Riverhead. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Splish Splash Water Park and Tanger Outlet Center are located nearby. Discover genuine guest reviews for Residence Inn by Marriott New York Long Island East End along with the latest prices and availability – book now.
Hot tub
Pet-friendly
Hyatt Place Long Island East End

Hyatt Place Long Island East End

3 out of 5
451 East Main Street, Riverhead, NY
Free cancellation
The price is CA $203 per night
CA $203
per night
Apr. 28 - Apr. 29
Stay at this 3-star business-friendly hotel in Riverhead. Enjoy free WiFi, free parking, and a marina. Our guests praise the breakfast and the pool in our reviews. Popular attractions Splish Splash Water Park and Suffolk Theater are located nearby. Discover genuine guest reviews for Hyatt Place Long Island East End along with the latest prices and availability – book now.
Pet-friendly
Pool
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
Free cancellation
Reserve now, pay when you stay
The price is CA $377 per night
CA $377
per night
Apr. 28 - Apr. 29
Stay at this spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the restaurant in our reviews. Popular attractions General William Hart House and Katharine Hepburn Cultural Arts Center are located nearby. Discover genuine guest reviews for Saybrook Point Resort & Marina, in Old Saybrook Center neighborhood, along with the latest prices and availability – book now.
Sag Harbor Inn

Sag Harbor Inn

3.5 out of 5
45 West Water Street, Sag Harbor, NY
The price is CA $285 per night
CA $285
per night
Apr. 28 - Apr. 29
Stay at this 3.5-star business-friendly hotel in Sag Harbor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions The Hamptons Beaches and Off the Rocker are located nearby. Discover genuine guest reviews for Sag Harbor Inn along with the latest prices and availability – book now.
Don't see what you're looking for?
See all available properties in Southold
View all properties
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.

Popular places to visit

Image for Sparkling Pointe

Sparkling Pointe

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.

Sparkling Pointe
Image for Croteaux Vineyards

Croteaux Vineyards

You can enjoy a tasting or tour at Croteaux Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

Croteaux Vineyards
Image for Sannino's Bella Vita Vineyard

Sannino's Bella Vita Vineyard

You can enjoy a tasting or tour at Sannino's Bella Vita Vineyard during your travels to Southold. Wander the beaches or discover the sunsets in this family-friendly area.

Sannino's Bella Vita Vineyard

Frequently asked questions

How much are vacation packages to Southold?
Treat yourself to a memorable experience in Southold with a vacation package starting from as low as CA $497. Booking flights and hotels with Travelocity is so simple. What’s more, our packages will leave you with more cash in your pocket for fun activities.
Where can I get the best vacation package deals for Southold?
You’ll find sensational Southold package deals with Travelocity. Pick and choose from as many as 400 air carriers and 665,000 properties worldwide and turn your travel dreams into a reality.
Why should I purchase my Southold vacation bundle via Travelocity?
Because you’ll never wander on your own if you lock in your vacation with us, and we offer 24/7 customer support and top-quality service to boot. Add to that our Price Match Guarantee and countless destinations and experiences to select from. It’s our job to help you have the vacation of a lifetime.
Can I save on my Southold car rental if I combine it with a hotel or flight?
Absolutely. And our Southold vacation packages are the best way to do it. With just a few clicks you can save cash as well as time by combining your bookings. Collect the keys to your rental car then set your own course. Searching for things to do? Throw some tours or experiences into your package and save on those too.
What is the best time of year to go to Southold?
are the months when most people visit, while are usually less busy. If your budget is limited, contemplate visiting around . is usually regarded as the priciest time of year to come here.
Can I go on vacation to Southold at this time?
Don’t fly off to Southold without the facts about quarantine policies and travel restrictions. Travelocity’s Covid-19 Travel Advisor will fill you in. Our travel experts have pulled together all the information you need to make your getaway as hassle-free as possible.