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.
Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was CA $1,648, price is now CA $971 per person
CA $971
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
Book a stay at this business-friendly hotel in New York. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Yankee Stadium and Central Park are located nearby.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $6,191, price is now CA $3,693 per person
CA $3,693
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop 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.
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was CA $3,361, price is now CA $2,117 per person
CA $2,117
per person
Oct 13 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, a rooftop terrace, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brooklyn Bridge and Wall Street are located nearby.
The Hoxton, Williamsburg

The Hoxton, Williamsburg

4 out of 5
Price was CA $3,146, price is now CA $1,995 per person
CA $1,995
per person
Sep 15 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
Stay at this hotel in Brooklyn. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brooklyn Bridge and Grand Central Terminal are located nearby.
5th & 55th Residence Club

5th & 55th Residence Club

5 out of 5
Manhattan
Price was CA $13,455, price is now CA $8,599 per person
CA $8,599
per person
Oct 22 - Oct 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Popular attractions 5th Avenue and Radio City Music Hall 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 $394 per night
CA $394
CA $570 total
Sep 2 - Sep 3
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 Railroad Museum of Long Island and The Old Field Vineyards 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 $341 per night
CA $341
CA $389 total
Aug 18 - Aug 19
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 Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is CA $449 per night
CA $449
CA $548 total
Sep 1 - Sep 2
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 $979 per night
CA $979
CA $1,119 total
Aug 4 - Aug 5
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.
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
The price is CA $443 per night
CA $443
CA $578 total
Sep 2 - Sep 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
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road) Greenport NY
The price is CA $472 per night
CA $472
CA $664 total
Aug 4 - Aug 5
includes taxes & fees
Book a stay at this beach aparthotel in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and East End Seaport Maritime Museum are located nearby.
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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

Sunflowers in a field with a building in the background.
Photo by 4 Star Traveler
Open Photo by 4 Star Traveler

Pindar Vineyards

8.4/10 (8 reviews)
You can enjoy a tasting or tour at Pindar Vineyards during your travels to Peconic. Discover the area's sunsets and wineries.
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 $971. 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.