Village of Southampton Vacation Packages

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Your Village of Southampton Vacation

When you book a vacation package to Village of Southampton, you can relax and enjoy your break knowing that all your travel plans have been worked out ahead of time. Uncover the many wonders of this amazing city while based in a neighborhood like Montclair Colony, which is good for walking. Make your trip to Village of Southampton even more fulfilling by going sightseeing. Coopers Beach, Shinnecock Nation Cultural Center and Museum and Shinnecock Hills Golf Course are some of the leading attractions you'll want to explore. Stop daydreaming and start traveling. Browse the multitude of options on Expedia today and finally put your Village of Southampton vacation plans into gear!

Top Village of Southampton Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was CA $1,592, price is now CA $994 per person
CA $994
per person
Apr 26 - May 1
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Extremely clean. Staff very courteous. One of the best dining areas for breakfast/dinner food service.

Reviewed on Feb 21, 2026

Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Price was CA $2,439, price is now CA $1,545 per person
CA $1,545
per person
May 10 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.2/10 Good! (2,562 reviews)
Very nice and clean

Reviewed on Feb 20, 2026

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was CA $5,009, price is now CA $3,318 per person
CA $3,318
per person
Apr 2 - Apr 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Newark Liberty Intl. Airport (EWR)
9.6/10 Exceptional! (159 reviews)
EVERYTHIING WAS 👌. 6 stars! Thank you Karla and the wonderful team.

Reviewed on Feb 21, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $2,834, price is now CA $1,881 per person
CA $1,881
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
Very amazing place, everything is picture worthy.

Reviewed on Feb 21, 2026

Pendry Natirar

Pendry Natirar

5 out of 5
Price was CA $2,875, price is now CA $1,946 per person
CA $1,946
per person
Apr 9 - Apr 12
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Newark Liberty Intl. Airport (EWR)
9.8/10 Exceptional! (7 reviews)
The staff is lovely and the property gorgeous. The room could have been more complete (no slippers to be found and no in-room mini bar amenities, which was surprising). The grounds are pristine and peaceful.

Reviewed on Jun 13, 2025

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Village of Southampton Hotel Deals

Harpoon House

Harpoon House

3 out of 5
136 Main St Southampton NY
8.4/10 Very Good! (149 reviews)
Room was clean. Bathroom was refinished.

Reviewed on Feb 15, 2026

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Harpoon House
Southampton Inn

Southampton Inn

3 out of 5
91 Hill Street Southampton NY
The price is CA $205 per night from Feb 26 to Feb 27
CA $205
CA $257 total
Feb 26 - Feb 27
includes taxes & fees
8.6/10 Excellent! (556 reviews)
just a nice comfy feeling

Reviewed on Jan 29, 2026

Southampton Inn
Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom

Southampton NY
The price is CA $616 per night from Feb 27 to Feb 28
CA $616
CA $1,518 total
Feb 27 - Feb 28
includes taxes & fees
10/10 Exceptional! (3 reviews)
perfect for families

Reviewed on Oct 13, 2025

Minutes from the beach, brand new 4 bedroom
See all 4,069 properties in Village of Southampton
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.
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All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Village of Southampton

Cooper\'s Beach

Cooper's Beach

Escape NYC to play in the waves, sunbathe on fine, white sands or stroll past the exclusive mansions that line the dunes of one of the best beaches in the Hamptons.

Cooper's Beach
Shinnecock Museuem and Cultural Center featuring heritage elements

Shinnecock Nation Cultural Center and Museum

Learn about the traditional ways of life of the Shinnecock and admire indigenous artworks in Long Island’s only Native American-owned and operated museum.

Shinnecock Nation Cultural Center and Museum

Southampton Arts Center

After visiting Southampton Arts Center, make a plan to see the other sights and activities in Village of Southampton. While you're in the area, stroll along the beautiful beaches.

Southampton Arts Center

What to do in Village of Southampton

great fun with friends

Full Day Private Long Island Wine Tours from New York City

CA $261
per adult
Full Day Private Long Island Wine Tours from New York City
East Hampton Shops

Hamptons Private Day Trip from New York City

CA $1,772
per traveller
Hamptons Private Day Trip from New York City
Wine and grapes against the sea

The Hamptons and Long Island Wineries Private Tour

CA $1,772
per traveller
The Hamptons and Long Island Wineries Private Tour
See all activities in Village of Southampton

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.