Westchester Vacation Packages
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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.
Top Holiday Package Deals in Westchester
Price found within the past 48 hours. Click for updated prices.
Luxuri Suites
South Beach
Price was CA $1,133, price is now CA $666 per person
CA $666
per person
Sep 8 - Sep 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
6.8/10 (55 reviews)
Ok the fact we had no desk for check was terrible. I could not check in due to a code for door and room acess never being sent to my email resulted in me not checking for 3hours until I was told about a sister property 3 blocks from where I was stay had to walk in the rain to the siater property for thwm to grant me acess codes to get into my room now at 3am. I wouls likw to be reemburst for that night and day. My TV had no working batteries and once I go batteries the TV volum did not work.
Reviewed on Jul 9, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was CA $25,812, price is now CA $14,163 per person
CA $14,163
per person
Sep 3 - Sep 8
found 18 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) 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
Casablanca Miami Beach
North Beach
Price was CA $2,372, price is now CA $1,353 per person
CA $1,353
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Miami (MIA)
5.8/10 (324 reviews)
This was a very disappointing stay. The apartment was dirty, dusty, and hot. The temperature stayed around 77–78°F all night, yet the only bedding provided was thick comforters, making it impossible to sleep comfortably.
When I simply asked for thin bed sheets, the host became argumentative instead of trying to help. They kept saying they were a private owner, as if that somehow excused poor customer service or making guests uncomfortable. It wasn’t until I contacted Expedia that the host responded by providing what I initially asked for.
I didn’t want to spend my vacation dealing with unnecessary conflict, so we checked out after the first night instead of staying for the remaining five nights of our six-night reservation. I would not stay here again.
Reviewed on Jul 2, 2026
The Local House
South Beach
Price was CA $1,646, price is now CA $1,043 per person
CA $1,043
per person
Aug 16 - Aug 21
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.2/10 Wonderful! (1,002 reviews)
We only stayed for one night before driving down to the keys for my birthday but we really enjoyed our stay at The Local House. All of the staff were incredibly kind and they even blew up balloons and decorated our room for my birthday. Considering how busy the area was, the rooms were incredibly quiet and the bed was super comfortable. The only complaint we would have is that the bathrooms are slightly outdated in comparison to the bedrooms but other than that, we really enjoyed our stay and would recommend The Local House to anyone looking to stay in South Beach.
Reviewed on Jul 5, 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(1,197 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 CA $420 per night from Jul 26 to Jul 27
CA $420
CA $574 total
Jul 26 - Jul 27
includes taxes & fees
8.4/10 Very good! (8,589 reviews)
"It nice very beautiful!!"
Reviewed on Jul 9, 2026
Loews Miami Beach Hotel – South Beach
1601 Collins Ave Miami Beach FL
The price is CA $282 per night from Jul 21 to Jul 22
CA $282
CA $401 total
Jul 21 - Jul 22
includes taxes & fees
9.4/10 Exceptional! (913 reviews)
"I will not visit in the future."
Reviewed on Jul 9, 2026
Miami International Airport Hotel
N.W. 20th & Lejeune Road Miami FL
Fully refundableReserve now, pay when you stay
The price is CA $276 per night from Aug 9 to Aug 10
CA $276
CA $312 total
Aug 9 - Aug 10
includes taxes & fees
7.8/10 Good! (5,568 reviews)
"Inside of airport"
Reviewed on Jul 8, 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
Stay near popular Westchester attractions
Things to do
Miami Big Bus Panoramic Night Tour
CA $40
per adult
88% of travellers recommend
Thrilling Speedboat + Sightseeing Tour of Miami
CA $72
per adult
94% of travellers recommend
Miami Skyline Evening Cruise of Biscayne Bay with stop at South Beach
CA $48
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.