Book Exclusive Town of Southold Town Vacation Packages

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A lighthouse on a rocky outcrop with a boat in the water.

Orient

Vacations
Orient
A coastal landscape with a sandy beach, calm water, and scattered trees.

East Marion

Vacations
East Marion

Town of Southold Town flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Save 100% on your flight
Price was CA $1,958, price is now CA $1,125 per person
CA $1,125
per person
Nov 30 - Dec 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, a steam room, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Central Park and Manhattan Cruise Terminal are located nearby.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was CA $4,879, price is now CA $2,970 per person
CA $2,970
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
Book a stay at this luxury hotel in Brooklyn. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Brooklyn Bridge and Wall Street are located nearby.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was CA $3,055, price is now CA $1,892 per person
CA $1,892
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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.
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was CA $5,646, price is now CA $3,561 per person
CA $3,561
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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 helpful staff in our reviews. Popular attractions 5th Avenue and Rockefeller Center are located nearby.
Smyth Tribeca

Smyth Tribeca

4.5 out of 5
Manhattan
Save 100% on your flight
Price was CA $3,408, price is now CA $2,197 per person
CA $2,197
per person
Nov 30 - Dec 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Brooklyn Bridge and Wall Street are located nearby.

Top Town of Southold Town hotels deals

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is CA $243 per night
CA $243
CA $319 total
Nov 4 - Nov 5
includes taxes & fees
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 attractions Hashamomuck Pond and Railroad Museum of Long Island are located nearby.
On private beach
Pool
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
The price is CA $260 per night
CA $260
CA $297 total
Oct 12 - Oct 13
includes taxes & fees
Book a stay at this boutique hotel in Greenport. Enjoy free parking, free bicycles on site, and daily housekeeping. Popular attractions Greenport Harbor Brewing Company and Greenport Farmers' Market are located nearby.
Pet-friendly
Parking included
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
The price is CA $230 per night
CA $230
CA $303 total
Nov 2 - Nov 3
includes taxes & fees
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 rooms in our reviews. Popular attractions Greenport Carousel and Camera Obscura are located nearby.
Pool
Breakfast included
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

4 out of 5
1400 Silvermere Rd Greenport NY
The price is CA $327 per night
CA $327
CA $374 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this beach hotel in Greenport. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Railroad Museum of Long Island and East End Seaport Maritime Museum are located nearby.
On private beach
Spa
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is CA $345 per night
CA $345
CA $430 total
Nov 8 - Nov 9
includes taxes & fees
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 The Old Field Vineyards and Crescent Beach are located nearby.
Free WiFi
Restaurant
North Fork Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
The price is CA $346 per night
CA $346
CA $395 total
Oct 13 - Oct 14
includes taxes & fees
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' Market are located nearby.
Pool
Pet-friendly
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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 Town of Southold Town attractions

A rocky shoreline with large boulders and a calm sea.

Orient Point County Park

10.0/10 (1 review)
Explore the great outdoors at Orient Point County Park, a lovely green space in Orient Point. Stroll along the beaches or discover the area's sunsets.
See properties

Photos of local treasures

Browse Town of Southold Town vacation photos for more inspiration

A white colonial-style house with a green roof and a lighthouse tower.
A sandy beach with footprints leading to the water, a clear blue sky, and a few buildings in the distance.
A beach at sunset with calm waters and a rocky shoreline.
A pebbled beach with large rocks and seaweed.
A marina with boats, a lighthouse, and a grassy area with a tree.

Frequently asked questions

How much are vacation packages to Town of Southold Town?
Spoil yourself with an unforgettable travel experience in Town of Southold Town with a vacation package starting at CA $1,125. Locking in flights, tours and hotels through Travelocity is simple. And even better, our great deals will leave you with more savings in your pocket for plenty of fun times.
How long should my Town of Southold Town vacation be?
Around 2 nights is the average amount of time travelers vacation in Town of Southold Town. But the perfect trip length depends on how many cherished memories you want to make. Why not stay a little longer and explore some off-the-beaten-path gems?
Where can I get the best vacation package deals for Town of Southold Town?
Travelocity has all you need to score an awesome Town of Southold Town package deal. Choose from 400 partner airlines and 1,000,000 properties all over the globe and create a travel itinerary that's perfect for you. With this amount of choice, you have inspiration galore for your next big adventure.
Why should I purchase my Town of Southold Town vacation bundle with Travelocity?
We offer 24/7 customer support, exceptional service and a Price Match Guarantee. Life is all about the journey — and we have amazing destinations for you to journey to all across the globe. Explore with us and your bank balance will thank you for it.
Can I save money on my Town of Southold Town car rental if I book it with my hotel or flight?
Combining your car, flight and hotel into a Town of Southold Town vacation package is an easy way to land the best deal. Plus, having your own rental car gives you total freedom to find your way to all those amazing sights you'd like to check out. Sitting 137 kilometers away from Town of Southold Town, Times Square is one place that should be on your itinerary. Buckle up and make a day trip of it.
Which airport is best for Town of Southold Town?
Bradley Intl. Airport (BDL) is 97 kilometers from the city center and is the starting point for many memorable experiences. Alternatively, MacArthur Airport (ISP) is 64 kilometers away from central Town of Southold Town and Tweed - New Haven Regional Airport (HVN) is 48 kilometers away from central Town of Southold Town.
What is there to do in Town of Southold Town?
There's a certain magic in the air as you stroll through the streets of Town of Southold Town. 67 Steps Beach and Greenport Carousel are just two attractions that make this city so popular, so add them to your to-do list.
Where should I stay when visiting Town of Southold Town?
Many people choose to check in to the The Blue Inn At North Fork. It's a great base for your Town of Southold Town vacation.