Westchester Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
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.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $12,963
per person
Nov 12 - Nov 17
found 1 day 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
Pelican Hotel
South Beach
CA $1,203
per person
Nov 12 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9.2/10 Wonderful! (499 reviews)
Location is fantastic, as it the restaurant. Staff was great. The room was very small, and the bed felt like concrete.
Reviewed on Sep 1, 2026
Elita Hotel
East Fort Lauderdale
CA $845
per person
Oct 3 - Oct 10
found 23 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.6/10 Excellent! (189 reviews)
Everything was just outstanding. Expect people were smoking in the stairs and it was inconvenient when you have kids passing by the stairs to go to the room.
Reviewed on Sep 2, 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
3 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.
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.
Downtown Miami
2 out of top 10 points of interest in this area
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.
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.
Flamingo/Lummus
If you're spending some time in Flamingo/Lummus, Collins Avenue Shopping Area and Miami Beach Boardwalk are top sights worth seeing.
Westchester Hotel Deals
Fontainebleau Miami Beach
4441 Collins Avenue Miami Beach FL
Fully refundableReserve now, pay when you stay
CA $311
CA $447 total
Sep 8 - Sep 9
includes taxes & fees
8.4/10 Very good! (8,876 reviews)
"the room wasn't clean,dissapointed"
Reviewed on Sep 2, 2026
Loews Miami Beach Hotel – South Beach
1601 Collins Ave Miami Beach FL
Fully refundableReserve now, pay when you stay
CA $294
CA $414 total
Oct 2 - Oct 3
includes taxes & fees
9.4/10 Exceptional! (1,484 reviews)
"Great hotel"
Reviewed on Sep 2, 2026
Hyatt Regency Miami
400 Se 2nd Ave Miami FL
Fully refundableReserve now, pay when you stay
CA $207
CA $234 total
Sep 8 - Sep 9
includes taxes & 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.
Frequently asked questions
How much does a Westchester vacation package cost?
Live it up in Westchester from as low as CA $811. 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.
Stay near popular Westchester attractions
Coral Way Shopping Area
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.
Coral Estates Park
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.
Bianco Bistro Cafe
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?
Things to do
Miami Sunset and City Lights Cocktail Cruise with Open Bar
CA $96
per adult
92% 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.