Westchester Vacations from ￥306,873

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    Save up to ￥45,448 when you book a flight and hotel together*

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

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The Latest Westchester Vacation Packages

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

President Hotel Villa

3.5 out of 5
South Beach
Price was ￥355,732, price is now ￥306,873 per person
￥306,873
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.2/10 Very Good! (997 reviews)
nice location, good room. nice breakfast and evening reception

Reviewed on Feb 22, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was ￥2,986,620, price is now ￥1,628,048 per person
￥1,628,048
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8/10 Very Good! (1 review)
The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Price was ￥552,419, price is now ￥422,141 per person
￥422,141
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
9.4/10 Exceptional! (56 reviews)
Clean room, excellent staff at the front desk, dining room, pool staff, and beach staff. Sergiy was especially helpful telling us all about the hotel.

Reviewed on Feb 13, 2026

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was ￥375,228, price is now ￥313,546 per person
￥313,546
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Loved the location, room was nice, bathroom very small, very friendly staff, slow service at restaurant in the morning. Will go back

Reviewed on Feb 24, 2026

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was ￥384,824, price is now ￥331,096 per person
￥331,096
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8/10 Very Good! (1,120 reviews)
Staff are great but the bed and pillows were uncomfortable. Especially the pillows they are horrible. I had to use a towel as my pillow. Other hotels have feather pillows that are far more comfortable. It would be nice to have a choice. For this reason we won’t return. It’s too bad because everything else was nice.

Reviewed on Feb 19, 2026

Where to stay in Westchester

Find the best Westchester areas and neighborhoods for the activities you enjoy most. Learn more about Westchester
Stunning view of South Beach shoreline with skyscrapers and cloudy skies in Miami Beach, Florida

South Beach

2 out of top 10 points of interest in this area
4.5/5(11,595 area reviews)

Major entertainment destination with numerous nightclubs, restaurants, and boutiques. Stroll along Lincoln Road and Ocean Drive, admire Art Deco buildings, and enjoy easy access to public transportation.

Find hotels in South Beach

Westchester Hotel Deals

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
4441 Collins Avenue Miami Beach FL
Fully refundableReserve now, pay when you stay
The price is ￥50,361 per night from Mar 8 to Mar 9
￥50,361
￥67,896 total
Mar 8 - Mar 9
includes taxes & fees
8.4/10 Very Good! (7,920 reviews)
Room was not super clean - little stuff like a sticker and hair on the tub, drink can on the balcony. And I went to the terrific gym at 7:45 only to be told it closed at 8p. That's shameful. Coming from CA that's only 5p, but way too early regardless. They have NO business charging a fee if they're ...

Reviewed on Feb 27, 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 ￥88,792 per night from Mar 3 to Mar 4
￥88,792
￥109,050 total
Mar 3 - Mar 4
includes taxes & fees
9/10 Wonderful! (4,872 reviews)
Everything was amazing. Staff was so friendly!

Reviewed on Feb 26, 2026

Loews Miami Beach Hotel – South Beach
Park Central South Beach

Park Central South Beach

4 out of 5
640 Ocean Dr Miami Beach FL
Fully refundableReserve now, pay when you stay
The price is ￥42,296 per night from Mar 11 to Mar 12
￥42,296
￥56,213 total
Mar 11 - Mar 12
includes taxes & fees
8.6/10 Excellent! (896 reviews)
Our room was tiny with no chair or place to sit other than on the bed. There was no dresser or shelves or place to put clothes (there was one narrow closet with a couple of hangers). We had two windows both facing the back of other buildings and electrical wiring.

Reviewed on Feb 27, 2026

Park Central South Beach
See all 12,212 properties in Westchester
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 ￥306,873. 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.

Things to do

Double decker bus in Miami at night

Miami Big Bus Panoramic Night Tour

￥5,015
per adult
86% of travellers recommend
Miami Big Bus Panoramic Night Tour
Amazing Boat Tour in Miami with Transportation

Ultimate Miami Boat Tour : Mansions & Skyline with optional Pick-up

￥4,489
per adult
76% of travellers recommend
Ultimate Miami Boat Tour : Mansions & Skyline with optional Pick-up
Little Havana Food and Walking Tour in Miami

Little Havana Food and Walking Tour in Miami

￥10,833
per adult
98% of travellers recommend
Little Havana Food and Walking Tour in Miami
See all activities in Miami
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.