Save up to CA $4,200 when you book a flight and hotel together*
With over 300,000 hotels worldwide, it's easy to create a perfect package
Plan, book, and manage your trip all in one place
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.
Price found within the past 48 hours. Click for updated prices.
Trip length
3 nights4 nights5 nights6-7 nights
Stars
5 star4 star & up3 star & up2 star & up
Flight class
EconomyPremium economyBusinessFirst class
Remove all filters
Feb 6 - Feb 11
Tavernier
5 nights
7.8/10 - Good (1,023 reviews)
"The staff was friendly and welcoming and the restaurants were very close. On the 2nd day I needed a fresh set of towels and they delivered them quickly. I will stay there again if I'm in Tavanier."
Reviewed November 13, 2026
Roundtrip • Toronto (YYZ) - Miami (MIA)
YYZ - FLL • 1 stop FLL - YYZ • 1 stop
CA $675
per traveller
found 15 hours ago
Jan 15 - Jan 19
South Beach
4 nights
8.0/10 - 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 June 22, 2016
Roundtrip • Montreal (YMQ) - Miami (MIA)
YUL - MIA • 1 stop MIA - YUL • 1 stop
CA $15,853
per traveller
found 1 day ago
Jan 25 - Jan 30
Singer Island
5 nights
8.8/10 - Excellent (405 reviews)
"Did"
Reviewed November 14, 2026
Roundtrip • Toronto (YYZ) - Fort Lauderdale (FLL)
YYZ - MCO • Nonstop MCO - YYZ • Nonstop
CA $1,964
per traveller
found 1 day ago
Jan 5 - Jan 11
Downtown Miami
6 nights
9.0/10 - Wonderful (6 reviews)
"The apartment had not been cleaned thoroughly. The bed sheets were not clean and the floor was dirty. I would appreciate it if the cleaning could be done more carefully in the future."
Reviewed September 7, 2026
Roundtrip • Toronto (YTO) - Miami (MIA)
YYZ - FLL • Nonstop FLL - YYZ • Nonstop
CA $1,362
per traveller
found 1 day ago
Jan 5 - Jan 11
Downtown Miami
6 nights
Roundtrip • Toronto (YTO) - Miami (MIA)
YYZ - FLL • Nonstop MIA - YYZ • 1 stop
CA $1,519
per traveller
found 1 day ago
Find the best Westchester areas and neighborhoods for the activities you enjoy most.
Photo by Greater Miami Convention and Visitors Bureau
View properties in map for South Beach
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.
View properties in map for Brickell
A dense, high-rise residential area with upscale condos, Brickell boasts popular Miami restaurants, shops, and art galleries. Explore Mary Brickell Village or catch the Metromover for easy transportation.
View properties in map for Downtown Miami
An urban city center with a rich cultural scene, Downtown Miami offers shopping at Flagler Street, Bayside Marketplace, and Mary Brickell Village. Explore Pérez Art Museum Miami, Miami Children's Museum, and enjoy the pedestrian-friendly area with extensive public transit options.
Photo by Michael Finelli
View properties in map for Doral
A noteworthy feature of Doral is its popular shops. While you're in town, be sure to stop and check out CityPlace Doral and Miami International Mall.
Photo by Greater Miami Convention and Visitors Bureau
Photo by Lucas
View properties in map for Flamingo/Lummus
If you're spending some time in Flamingo/Lummus, Collins Avenue Shopping Area and Miami Beach Boardwalk are top sights worth seeing.
During your trip to Miami, you can enjoy retail therapy at Coral Way Shopping Area. While you're in the area, stroll along the beaches.
Bianco Bistro Cafe is just one of the places to see in Miami, so why not enjoy the other things to explore during your travels?
Coral Estates Park is just one of the places to see in Miami, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's picturesque gardens or attend a sporting event.
CA $49
per adult
70% of travellers recommend
CA $99
per adult
96% of travellers recommend
CA $41
per adult
86% of travellers recommend
See all activities near 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.
See all properties in Westchester
Live it up in Westchester from as low as CA $675. 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.
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!
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?
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?
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.
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.
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.
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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.