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.

Southampton

Vacations
Southampton

Town of Southampton flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
33 Hotel, New York City, Seaport

33 Hotel, New York City, Seaport

5 out of 5
Manhattan
Save 100% on your flight
Price was CA $3,083, price is now CA $1,850 per person
CA $1,850
per person
Dec 26 - Dec 31
found 20 hours ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Brooklyn Bridge and Wall Street are located nearby.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was CA $3,296, price is now CA $1,871 per person
CA $1,871
per person
Dec 10 - Dec 13
found 7 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
Book a stay at this luxury vacation home in Bridgeport. Enjoy free WiFi, free parking, and a garden. Popular attractions Beardsley Zoo and Lafayette Park are located nearby.
The Plaza, A Fairmont Hotel

The Plaza, A Fairmont Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was CA $11,308, price is now CA $7,129 per person
CA $7,129
per person
Dec 27 - Jan 2
found 21 hours ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions 5th Avenue and Radio City Music Hall are located nearby.
The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
Price was CA $6,006, price is now CA $3,790 per person
CA $3,790
per person
Nov 13 - Nov 16
found 4 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy free WiFi, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff in our reviews. Popular attractions 5th Avenue and Grand Central Terminal are located nearby.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was CA $3,012, price is now CA $1,947 per person
CA $1,947
per person
Nov 27 - Nov 29
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.

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 $127 per night
CA $127
CA $181 total
Oct 30 - Oct 31
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 Sebonack Golf Course and Shinnecock Hills Golf Course are located nearby.
Pool
Pet-friendly
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 $204 per night
CA $204
CA $233 total
Oct 21 - Oct 22
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 Sebonack Golf Course and Shinnecock Hills 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 $584 per night
CA $584
CA $734 total
Nov 2 - Nov 3
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 Sag Harbor Whaling and Historical Museum are located nearby.
Pool
Spa
Hampton Bays Hotel on Main

Hampton Bays Hotel on Main

2 out of 5
2 W Montauk Hwy Hampton Bays NY
The price is CA $168 per night
CA $168
CA $192 total
Oct 8 - Oct 9
includes taxes & fees
Stay at this hotel in Hampton Bays. Enjoy free WiFi, 2 bars/lounges, and cable TV channels. Popular attractions Good Ground Park and Meschutt Beach are located nearby.
Free WiFi
Air conditioning
The Hampton Maid

The Hampton Maid

2.5 out of 5
259 E Montauk Hwy Hampton Bays NY
The price is CA $302 per night
CA $302
CA $345 total
Oct 13 - Oct 14
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 Meschutt Beach and Good Ground Park are located nearby.
Pool
Spa
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 $127 per night
CA $127
CA $145 total
Oct 7 - Oct 8
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 All Star Bowling and Suffolk Theater are located nearby.
Pool
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 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 $1,850. 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.