Westchester Vacations from ￥307,032

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

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

    Find the right fit

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

    Rest easy

    Plan, book, and manage your trip all in one place

The Latest Westchester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Gabriel Miami South Beach, Curio Collection by Hilton

The Gabriel Miami South Beach, Curio Collection by Hilton

4 out of 5
South Beach
per person
Sep 13 - Sep 16
found 10 hours ago
Roundtrip flight included
Tokyo (TYO) to Miami (MIA)
8.2/10 Very Good! (877 reviews)
Ok could be a lot better

Reviewed on Jul 26, 2025

EAST Miami

EAST Miami

5 out of 5
Downtown Miami
per person
Sep 13 - Sep 16
found 10 hours ago
Roundtrip flight included
Tokyo (TYO) to Miami (MIA)
9.2/10 Wonderful! (3,202 reviews)
Excellent property. Can’t wait to stay again.

Reviewed on Jul 26, 2025

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
per person
Sep 13 - Sep 16
found 10 hours ago
Roundtrip flight included
Tokyo (TYO) to Miami (MIA)
8/10 Very Good! (6,535 reviews)
We had a great stay. Great property. We took advantage of bicycle rental, banana boat rides, and outdoor exercise classes. Food and drink prices are very high but that was what I anticipated. Family of three with a teen son.

Reviewed on Jul 26, 2025

Kimpton EPIC Hotel by IHG

Kimpton EPIC Hotel by IHG

5 out of 5
Downtown Miami
per person
Sep 13 - Sep 16
found 10 hours ago
Roundtrip flight included
Tokyo (TYO) to Miami (MIA)
8.8/10 Excellent! (1,881 reviews)
Everything I love this hotel , the water views are the best

Reviewed on Jul 26, 2025

Eden Roc Miami Beach

Eden Roc Miami Beach

4.5 out of 5
Mid Beach
per person
Sep 13 - Sep 16
found 10 hours ago
Roundtrip flight included
Tokyo (TYO) to Miami (MIA)
8.4/10 Very Good! (2,739 reviews)
Nice hotel and amenities. Management could have been better.

Reviewed on Jul 26, 2025

Where to stay in Westchester

Find the best Westchester areas and neighborhoods for the activities you enjoy most. Learn more about Westchester
South Beach featuring skyline, swimming and a sandy beach

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 ￥45,060 per night from Jul 28 to Jul 29
￥45,060
￥60,291 total
Jul 28 - Jul 29
includes taxes & fees
8/10 Very Good! (6,651 reviews)
Beautiful beach
"Very nice hotel Beautiful beach and pools area"

Reviewed on Jul 25, 2025

Fontainebleau Miami Beach
Kimpton EPIC Hotel by IHG

Kimpton EPIC Hotel by IHG

5 out of 5
270 Biscayne Blvd Way, Miami, FL
Fully refundableReserve now, pay when you stay
The price is ￥26,466 per night from Aug 20 to Aug 21
￥26,466
￥36,582 total
Aug 20 - Aug 21
includes taxes & fees
8.8/10 Excellent! (1,939 reviews)
"Everything I love this hotel , the water views are the best"

Reviewed on Jul 26, 2025

Kimpton EPIC Hotel by IHG
citizenM Miami Worldcenter

citizenM Miami Worldcenter

4 out of 5
700 NE 2ND AVENUE, Miami, FL
Fully refundableReserve now, pay when you stay
The price is ￥13,440 per night from Aug 5 to Aug 6
￥13,440
￥15,186 total
Aug 5 - Aug 6
includes taxes & fees
9.2/10 Wonderful! (4,817 reviews)
"I really likes this place for many reasons, it’s easy going , friendly staff , but start lacking of fine detail and clean areas and furniture of the room"

Reviewed on Jul 24, 2025

citizenM Miami Worldcenter
See all 12,824 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 ￥307,032. 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

Miami: 1-hour Jetcar Rental

Miami: 1-hour Jetcar Rental

￥7,181
per traveler
84% of travellers recommend
Miami: 1-hour Jetcar Rental
Miami Skyline Evening Cruise on Biscayne Bay

Miami Skyline Evening Cruise of Biscayne Bay on luxury yacht

￥3,847
per adult
Miami Skyline Evening Cruise of Biscayne Bay on luxury yacht
Official Miami Millionaires Sightseeing Cruise

Official Miami Millionaires Sightseeing Cruise

￥2,639
per adult
84% of travellers recommend
Official Miami Millionaires Sightseeing Cruise
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.