Long Island Luxury Vacations 2026

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Top Luxury vacation packages in Long Island

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

Aura Hotel Brooklyn

$498

per person

Oct 16 - Oct 18

found 21 hours ago

Roundtrip flight included

Buffalo (BUF) to New York (JFK)

8/10 Very Good! (1,271 reviews)

The room felt dingy but was fine for a one-night stay. We liked the location and the price was ok considering how expensive Brooklyn has gotten!

Reviewed on Aug 11, 2026

1 Hotel Brooklyn Bridge

Save 100% on your flight

$1,702

per person

Oct 16 - Oct 19

found 16 hours ago

Roundtrip flight included

Chicago (CHI) to New York (JFK)

9/10 Wonderful! (1,012 reviews)

Didn’t allow me to get late checkout . Upon arrival the valet wasn’t even outside to help with baggage , for such an expensive hotel , I’d say my expectations were completely unmet

Reviewed on Aug 16, 2026

The Inn At Fox Hollow Hotel

Save 100% on your flight

$845

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip flight included

Fort Lauderdale (FLL) to New York (JFK)

9.2/10 Wonderful! (1,000 reviews)

Clean room, comfortable bed, great front desk staff and plentiful breakfast!!

Reviewed on Aug 15, 2026

The William Vale

Save 100% on your flight

$1,126

per person

Oct 16 - Oct 18

found 20 hours ago

Roundtrip flight included

Buffalo (BUF) to New York (JFK)

9/10 Wonderful! (1,141 reviews)

The Box House Hotel

Save 100% on your flight

$744

per person

Oct 16 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTT) to New York (JFK)

9/10 Wonderful! (1,001 reviews)

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See all available trips from Columbus to Long Island

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5* Luxury vacations in Long Island

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

The William Vale

Save 100% on your flight

$1,126

per person

Oct 16 - Oct 18

found 20 hours ago

Roundtrip flight included

Buffalo (BUF) to New York (JFK)

9/10 Wonderful! (1,141 reviews)

1 Hotel Brooklyn Bridge

Save 100% on your flight

$1,702

per person

Oct 16 - Oct 19

found 16 hours ago

Roundtrip flight included

Chicago (CHI) to New York (JFK)

9/10 Wonderful! (1,012 reviews)

Didn’t allow me to get late checkout . Upon arrival the valet wasn’t even outside to help with baggage , for such an expensive hotel , I’d say my expectations were completely unmet

Reviewed on Aug 16, 2026

Don't see what you're looking for?

See all available trips from Columbus to Long Island

View all trips

3 Night Luxury vacations in Long Island

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

Aura Hotel Brooklyn

Save 100% on your flight

$595

per person

Oct 16 - Oct 19

found 15 hours ago

Roundtrip flight included

San Juan (SJU) to New York (JFK)

8/10 Very Good! (1,271 reviews)

The room felt dingy but was fine for a one-night stay. We liked the location and the price was ok considering how expensive Brooklyn has gotten!

Reviewed on Aug 11, 2026

1 Hotel Brooklyn Bridge

Save 100% on your flight

$1,702

per person

Oct 16 - Oct 19

found 16 hours ago

Roundtrip flight included

Chicago (CHI) to New York (JFK)

9/10 Wonderful! (1,012 reviews)

Didn’t allow me to get late checkout . Upon arrival the valet wasn’t even outside to help with baggage , for such an expensive hotel , I’d say my expectations were completely unmet

Reviewed on Aug 16, 2026

The Inn At Fox Hollow Hotel

Save 100% on your flight

$701

per person

Oct 30 - Nov 2

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to New York (JFK)

9.2/10 Wonderful! (1,000 reviews)

Clean room, comfortable bed, great front desk staff and plentiful breakfast!!

Reviewed on Aug 15, 2026

Don't see what you're looking for?

See all available trips from Columbus to Long Island

View all trips

4 Night Luxury vacations in Long Island

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

Adria Hotel And Conference Center

Queens

Save 100% on your flight

$586

per person

Oct 16 - Oct 20

found 1 hour ago

Roundtrip flight included

Charlotte (CLT) to New York (JFK)

8.2/10 Very Good! (1,043 reviews)

The Inn At Fox Hollow Hotel

Save 100% on your flight

$845

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip flight included

Fort Lauderdale (FLL) to New York (JFK)

9.2/10 Wonderful! (1,000 reviews)

Clean room, comfortable bed, great front desk staff and plentiful breakfast!!

Reviewed on Aug 15, 2026

Aura Hotel Brooklyn

Save 100% on your flight

$788

per person

Sep 18 - Sep 22

found 1 hour ago

Roundtrip flight included

Fort Lauderdale (FLL) to New York (JFK)

8/10 Very Good! (1,271 reviews)

The room felt dingy but was fine for a one-night stay. We liked the location and the price was ok considering how expensive Brooklyn has gotten!

Reviewed on Aug 11, 2026

Don't see what you're looking for?

See all available trips from Columbus to Long Island

View all trips

What can I expect from a luxury Long Island vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Long Island vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

How can I find all-inclusive luxury vacation packages in Long Island?

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger. 

Can I book a cheap Long Island luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $498. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Long Island?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

Can I book a package in Long Island with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.   

How can I find the best luxury vacation deals in Long Island?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

Can I book a luxury holiday in Long Island with free cancellation and/or flexible dates?

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

Why should I book my luxury trip to Long Island with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.

Top Luxury Long Island Hotels

The William Vale

111 North 12th Street Brooklyn NY

7 min drive from Barclays Center Brooklyn

Discover luxurious lodging at The William Vale, where you can enjoy amenities like Champagne service, plush bedding, and more. The outdoor pool, poolside bar, ...

The Boro Hotel

38-28 27th Street Long Island City NY

14 min drive from Barclays Center Brooklyn

Treat yourself to a luxury stay at The Boro Hotel, where you can enjoy amenities like pillowtop beds, Egyptian cotton sheets, and more. Deluxe amenities at this ...

Viana Hotel and Spa, Trademark Collection by Wyndham

3998 Brush Hollow Rd Westbury NY

1 hour drive from Barclays Center Brooklyn

Pamper yourself with a luxury stay at Viana Hotel and Spa, Trademark Collection by Wyndham, where you can enjoy amenities like Champagne service, Frette Italian ...

8.8/10 Excellent! (1,008 reviews)

"Room was clean, staff very helpful. Pool and hot tub were utilized and fully enjoyed but the pool is very small."

Reviewed on Aug 15, 2026

See all 8,568 properties in Long Island

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.