Book Exclusive Town of Southampton Vacation Packages

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A beach with a wooden fence, a lifeguard tower, and a house with a balcony overlooking the ocean.

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Southampton

Town of Southampton flight + hotel packages

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

Lotte New York Palace

4.5 out of 5
Manhattan
Price was CA $2,161, price is now CA $1,426 per person
CA $1,426
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grand Central Terminal and 5th Avenue are located nearby.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $3,476, price is now CA $1,829 per person
CA $1,829
per person
Oct 4 - Oct 7
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.
Seven Beach Lane

Seven Beach Lane

2 out of 5
Price was CA $2,623, price is now CA $1,683 per person
CA $1,683
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
Stay at this hotel in Westhampton Beach. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Shock Ice Cream and Westhampton Beach Performing Arts Center are located nearby.
The High Line Hotel

The High Line Hotel

4 out of 5
Manhattan
Price was CA $2,282, price is now CA $1,473 per person
CA $1,473
per person
Nov 15 - Nov 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, free bicycles on site, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Madison Square Garden and Bryant Park are located nearby.
Topping Rose House

Topping Rose House

4.5 out of 5
Price was CA $5,885, price is now CA $3,939 per person
CA $3,939
per person
Oct 4 - Oct 10
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
Book a stay at this luxury hotel in Bridgehampton. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions The Hamptons Beaches and East Hampton Main Beach are located nearby.

Top Town of Southampton hotels deals

The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
The price is CA $271 per night
CA $271
CA $344 total
Sep 8 - Sep 9
includes taxes & fees
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 Cooper's Beach and Sebonack Golf Course are located nearby.
Pool
Pet-friendly
Hampton's Vacation Inn

Hampton's Vacation Inn

2.5 out of 5
177 West Montauk Highway Hampton Bays NY
The price is CA $279 per night
CA $279
CA $318 total
Aug 31 - Sep 1
includes taxes & fees
Stay at this guesthouse in Hampton Bays. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Regal UA Hampton Bays and Good Ground Park are located nearby.
Pool
Pet-friendly
Budget Host East End

Budget Host East End

2 out of 5
30 Lake Avenue Riverhead NY
Free cancellation
Reserve now, pay when you stay
The price is CA $172 per night
CA $172
CA $197 total
Aug 26 - Aug 27
includes taxes & fees
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 Splish Splash Water Park and All Star Bowling are located nearby.
Pool
Parking included
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
Free cancellation
Reserve now, pay when you stay
The price is CA $211 per night
CA $211
CA $275 total
Sep 20 - Sep 21
includes taxes & fees
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 rooms in our reviews. Popular attractions Cooper's Beach and Sebonack Golf Course are located nearby.
Pool
Pet-friendly
Faraway Sag Harbor

Faraway Sag Harbor

4 out of 5
31 West Water Street Sag Harbor NY
The price is CA $929 per night
CA $929
CA $1,167 total
Sep 15 - Sep 16
includes taxes & fees
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 The Hamptons Beaches and Off the Rocker are located nearby.
Pool
Spa
The Hampton Maid

The Hampton Maid

2.5 out of 5
259 E Montauk Hwy Hampton Bays NY
The price is CA $359 per night
CA $359
CA $410 total
Sep 8 - Sep 9
includes taxes & fees
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 Cooper's Beach and Meschutt Beach are located nearby.
Pool
Spa
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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 Southampton attractions

A beach with sand dunes and a person walking along the shore.

Cooper's Beach

9.2/10 (171 reviews)
Why not spend a carefree afternoon at Cooper's Beach during your travels in Village of Southampton? Wander the seaside or discover the area's sunsets.
See properties

Photos of local treasures

Browse Town of Southampton vacation photos for more inspiration

A man carrying a woman in front of a pool with two American flags, surrounded by greenery and a monument.
A rocky shoreline with clear blue water, a sandy beach, and a distant forested island.
A wooden boardwalk leading to a beach with a flagpole and an American flag.
A person standing on a sandy beach with footprints, looking out at the ocean with waves.
A two-story brick building with a marquee sign reading "WESTHAMPTON" and an American flag above the entrance.

Frequently asked questions

How much are vacation packages to Town of Southampton?
You'll be surprised — you can unwind in Town of Southampton for just CA $1,426. Here at Travelocity, we save you time and stress with our fantastic vacation packages. With flights, hotels and experiences all ready to go, what's holding you back?
How long should my Town of Southampton vacation be?
Generally, travelers spend 2 nights in Town of Southampton. However, that mightn't be long enough for you. If you're eager to explore some of the area's hidden treasures, how about adding a couple of extra nights to your travel itinerary?
Where can I get the best vacation package deals for Town of Southampton?
No matter how you like to travel, Travelocity can help you get an unbeatable Town of Southampton package deal. All you need to do is select a combination from our 400 air carriers and 1,000,000 worldwide properties.
Why should I purchase my Town of Southampton vacation bundle via Travelocity?
From our 24/7 support to our range of terrific destinations, we are dedicated to giving you the most unforgettable escape. All you'll have to do is click and book — our Price Match Guarantee will make sure you get the lowest price.
Can I save money on my Town of Southampton car rental if I bundle it with my hotel or flight?
You most certainly can — bundle your flight, car and hotel into a Town of Southampton vacation package and you can save plenty. With so much to see in Town of Southampton, having your own set of wheels will come in handy. Once you've slid into the driver's seat, put the stereo on and make your way to Times Square, a famous attraction about 129 kilometers from Town of Southampton.
Which airport is best for Town of Southampton?
MacArthur Airport (ISP) (48 kilometers away from downtown), Tweed - New Haven Regional Airport (HVN) (56 kilometers away from central Town of Southampton) and Hartford, CT (HFD-Hartford - Brainard) (97 kilometers away from central Town of Southampton) are all top options for Town of Southampton.
What is there to do in Town of Southampton?
There is a particular magic in the air as you stroll the streets of Town of Southampton. Wolffer Estates Vineyard and Long Island Aquarium and Exhibition Center are just two landmarks that make this city so popular, so add them to your itinerary.
Where should I stay when visiting Town of Southampton?
The Shorewood Inn is the first choice of many visitors. Book now before it's too late.