Westchester Vacations from $445
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Your Westchester Vacation
The easiest way to experience this interesting city is with a custom-made Westchester vacation package. Stay in the neighborhood of Coconut Grove, which is good for cafes, watersports and shopping or go someplace else — our packages are all about you. Fill your spare time with visits to University of Miami, Dadeland Mall and Miracle Mile, some of the things you should see during your trip to Westchester. Check out Expedia's extensive range of travel options and start organizing your dream vacation to Westchester today.
The Latest Westchester Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Avi Lux Stay
East Fort Lauderdale
Price was $2,216, price is now $978 per person
$978
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
7.6/10 Good! (10 reviews)
If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE.
Reviewed on Aug 28, 2025
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was $21,549, price is now $10,089 per person
$10,089
per person
Jan 28 - Feb 2
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 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 on Jun 22, 2016
72 Park Miami Beach Boutique Residences by IliosRentals
North Beach
Price was $2,289, price is now $1,141 per person
$1,141
per person
Jan 28 - Feb 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (18 reviews)
We had a wonderful stay with our group of three adults and three children! Everything was very comfortable, and the apartment was beautiful, clean, and well-maintained. There is a convenient shuttle service to the beach, but the 10-minute walk is also perfectly fine, even with children. Communication was excellent, and any questions we had were answered quickly. Overall, a very pleasant experience for the whole family. We would definitely recommend this place and would happily stay here again!
Reviewed on Oct 17, 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
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
$338 nightly
The price is $385 total per night from Nov 15 to Nov 16
$385 total
Nov 15 - Nov 16
Total with taxes and fees
Hyatt Regency Miami
400 Se 2nd Ave Miami FL
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $198 total per night from Nov 23 to Nov 24
$198 total
Nov 23 - Nov 24
Total with taxes and fees
8.8/10 Excellent! (2,825 reviews)
"I was pleased to find that the hotel bar and restaurant were still open when I made my late arrival from Miami airport at 9:30. My room was excellent, but the hotel is located within a canyon of giant buildings and loud engine noises were evident until well into the wee hours of the morning."
Reviewed on Nov 3, 2026
Kompose Boutique Hotel Miami Airport
3401 NW 25th St Miami FL
$89 nightly
The price is $101 total per night from Dec 1 to Dec 2
$101 total
Dec 1 - Dec 2
Total with taxes and fees
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.
Stay near popular Westchester attractions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.