Westchester Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ¥109,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Aug 7 - Aug 12

    Cavalier Hotel South Beach + Flight

    South Beach
    5 nights
    3.5 star property
    8.6/10 - Excellent (1,006 reviews)
    "Over was what I was loôking an hôtel you full like home by the beach and the ciné on South Beach"
    Reviewed May 30, 2026
    Roundtrip Tokyo (NRT) - Miami (MIA)
    NRT - MIA1 stop MIA - NRT1 stop
    ¥393,910
    ¥296,840
    per traveler
    found 1 day ago
    Cavalier Hotel South Beach
  • Aug 7 - Aug 12

    The Retreat Collection at 1 Hotel & Homes South Beach + Flight

    South Beach
    5 nights
    5.0 star property
    8.0/10 - Very Good (1 review)
    "Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay...."
    Reviewed June 22, 2016
    Roundtrip Tokyo (NRT) - Miami (MIA)
    NRT - MIA1 stop MIA - NRT1 stop
    ¥3,250,632
    ¥1,687,684
    per traveler
    found 20 hours ago
    The Retreat Collection at 1 Hotel & Homes South Beach
  • Aug 7 - Aug 12

    1 Hotel South Beach + Flight

    South Beach
    5 nights
    5.0 star property
    9.4/10 - Exceptional (1,529 reviews)
    "The shower for the size of the bathroom was too small. there was no shower niche and the stool in the shower was useless. Room service took way too long delivering extra blankets for the children."
    Reviewed May 31, 2026
    Roundtrip Tokyo (NRT) - Miami (MIA)
    NRT - MIA1 stop MIA - NRT1 stop
    ¥619,023
    ¥437,863
    per traveler
    found 1 day ago
    1 Hotel South Beach
  • Aug 7 - Aug 12

    Andaz Miami Beach Resort & Spa + Flight

    Mid Beach
    5 nights
    5.0 star property
    9.0/10 - Wonderful (298 reviews)
    "Amazing! 10 out of 10 highly recommend!"
    Reviewed June 1, 2026
    Roundtrip Tokyo (NRT) - Miami (MIA)
    NRT - MIA1 stop MIA - NRT1 stop
    ¥410,130
    ¥312,130
    per traveler
    found 1 day ago
    Andaz Miami Beach Resort & Spa
  • Aug 7 - Aug 12

    Fontainebleau Miami Beach + Flight

    Mid Beach
    5 nights
    4.5 star property
    8.4/10 - Very Good (8,314 reviews)
    "Excellent overall experience, but everything is expensive $$$$."
    Reviewed June 1, 2026
    Roundtrip Tokyo (NRT) - Miami (MIA)
    NRT - MIA1 stop MIA - NRT1 stop
    ¥426,017
    ¥331,784
    per traveler
    found 1 day ago
    Fontainebleau Miami Beach

Where to stay in Westchester

Find the best Westchester areas and neighborhoods for the activities you enjoy most. Learn more about Westchester

Westchester Hotel Deals

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
4441 Collins Avenue Miami Beach FL
The price is ¥43,369 per night from Jun 7 to Jun 8
¥43,369
¥60,153 total
Jun 7 - Jun 8
includes taxes & fees
8.4/10 Very Good! (8,314 reviews)
"Excellent overall experience, but everything is expensive $$$$."

Reviewed on Jun 1, 2026

Fontainebleau Miami Beach
Loews Miami Beach Hotel – South Beach

Loews Miami Beach Hotel – South Beach

4.5 out of 5
1601 Collins Ave Miami Beach FL
The price is ¥38,098 per night from Jun 5 to Jun 6
¥38,098
¥52,376 total
Jun 5 - Jun 6
includes taxes & fees
9.2/10 Wonderful! (605 reviews)
"Wonderful"

Reviewed on Jun 1, 2026

Loews Miami Beach Hotel – South Beach
Ramada by Wyndham Miami Springs/Miami International Airport

Ramada by Wyndham Miami Springs/Miami International Airport

2.5 out of 5
5001 NW 36th St. Miami Springs FL
Fully refundableReserve now, pay when you stay
The price is ¥10,193 per night from Jun 2 to Jun 3
¥10,193
¥11,519 total
Jun 2 - Jun 3
includes taxes & fees
8.2/10 Very Good! (6,429 reviews)
"Terrible"

Reviewed on Jun 1, 2026

Ramada by Wyndham Miami Springs/Miami International Airport
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.

Frequently asked questions

How much does a Westchester vacation package cost?
Live it up in Westchester from as low as . We offer a great selection of flights, rental cars and hotels to suit your travel style. Score even more discounts when you add a couple of activities or tours to your package.
How do I get a cheap travel package to Westchester?
Bundle your bookings with Expedia to save big on your next exciting adventure. With more than 550 partner airlines and 1,000,000 hotels across the globe, your Westchester vacation package can be customized exactly to suit your travel style. With all that extra money, why not add a few awesome activities and tours? It's an easy way to unlock even more savings. Your dream vacation in Westchester is much closer than you thought!
Where should I stay in Westchester?
Most visitors to Westchester put both PortMiami and Vizcaya Museum and Gardens on their bucket lists. Why not reserve a hotel that's close to these popular attractions?
What are the top hotels in Westchester?
Modern And New, Excellent Location Miami 1 and Modern And New, Excellent Location Miami 2 are a couple of the most well-known hotels in Westchester. Why not take a look at the facilities and amenities at each and then make up your mind?
How far in advance should I book my Westchester vacation?
While prices change frequently, we generally recommend booking your seats as early as possible. Most international airfares are available on Expedia up to a year in advance. If circumstances have left you booking last minute, you might still be in luck. Discount prices to Westchester sometimes occur in the weeks prior to departure.
What does an Expedia Westchester travel package include?
From hotels and airfares to car rentals, Expedia can help you create a Westchester package that suits you. Heading away for a week or longer? Give some thought to a hotel, rental car and flight bundle. If you're taking a short break, a hotel and airfare deal could suit you better. Experiences can also be added after you've booked. Our travel packages make it simple to plan and save.
What should I know before booking a Westchester travel package?
We already have low prices. However, you'll grab even more bargains if you book your hotels, flights and car rentals together. With an Expedia package, you'll always get transparent pricing and a great range of choice.
Can I choose my airline with a Westchester Expedia vacation package?
Yes, so take your pick! We offer more than 550 partner airlines globally, so you can tailor your Westchester trip according to your travel needs.
If I'm not able to travel, can I cancel my Westchester vacation package?
Whether it's your hotel, flight or rental car, you can cancel or amend it. Booked your Westchester vacation package in the last 24 hours? You may be able to make changes for free. For older bookings, you may be charged a fee by your airline, hotel or car rental company. For more details, browse our Customer Service Portal. We'll help you every step of the way.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.