
Westchester Vacations from ¥107,781
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ¥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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 Shelborne By Proper, a Member of Design Hotels
South Beach
Save 100% on your flight
Price was ¥440,548, price is now ¥258,910 per person
¥258,910
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
9.4/10 Exceptional! (56 reviews)
The holding fee is ridiculously high
Reviewed on Jan 8, 2026

President Hotel
South Beach
Save 100% on your flight
Price was ¥235,667, price is now ¥144,459 per person
¥144,459
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
8.4/10 Very Good! (1,775 reviews)
Spotless room and EXCELLENT staff. Also, location was perfect for our needs (drugstore, nearby shopping mall, and row of restaurants on Edpanola Way). We plan to return.
Reviewed on Jan 13, 2026

Bay Breeze Premium Apartments By Eskape Collection
Save 100% on your flight
Price was ¥243,531, price is now ¥158,084 per person
¥158,084
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
8.6/10 Excellent! (189 reviews)
Our two bedroom apartment was very comfortable and quiet. We enjoyed our stay very much.
Reviewed on Dec 30, 2025

Park Central South Beach
South Beach
Save 100% on your flight
Price was ¥254,703, price is now ¥177,556 per person
¥177,556
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
8.6/10 Excellent! (385 reviews)
It was great room, vibes, everything.
Reviewed on Jan 13, 2026
Where to stay in Westchester
Find the best Westchester areas and neighborhoods for the activities you enjoy most. Learn more about Westchester

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.
Westchester Hotel Deals

Fontainebleau Miami Beach
4441 Collins Avenue Miami Beach FL
Fully refundableReserve now, pay when you stay
The price is ¥99,417 per night from Jan 14 to Jan 15
¥99,417
¥122,883 total
Jan 14 - Jan 15
includes taxes & fees
8.2/10 Very Good! (7,628 reviews)
Great amenities
Reviewed on Jan 13, 2026

Park Central South Beach
640 Ocean Dr Miami Beach FL
Fully refundableReserve now, pay when you stay
The price is ¥25,578 per night from Jan 14 to Jan 15
¥25,578
¥36,359 total
Jan 14 - Jan 15
includes taxes & fees
8.6/10 Excellent! (647 reviews)
It was great room, vibes, everything.
Reviewed on Jan 13, 2026

Hilton Miami Airport Blue Lagoon
5101 Blue Lagoon Dr Miami FL
Fully refundableReserve now, pay when you stay
The price is ¥29,674 per night from Feb 10 to Feb 11
¥29,674
¥33,531 total
Feb 10 - Feb 11
includes taxes & fees
8/10 Very Good! (3,763 reviews)
Nice pool
Reviewed on Jan 9, 2026
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
Things to do

Miami: Off-Road ATV Guided Tour
¥2,349
per adult
74% of travellers recommend

Miami: Original Everglades Airboat Tour & Alligator Exhibit
¥6,106
per adult
78% of travellers recommend

Banana Boat Ride with Miami Watersports
¥4,086
per traveler
76% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



