Westchester Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, 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 W - Bayshore Unit 1003

The W - Bayshore Unit 1003

3 out of 5
East Fort Lauderdale
Price was CA $2,133, price is now CA $1,115 per person
CA $1,115
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
6/10 (2 reviews)
MirabileCondoDwntown MIA Brickell w PRKG

MirabileCondoDwntown MIA Brickell w PRKG

5 out of 5
Downtown Miami
Price was CA $3,498, price is now CA $1,482 per person
CA $1,482
per person
Jul 19 - Jul 24
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
2/10 (2 reviews)
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was CA $50,245, price is now CA $25,829 per person
CA $25,829
per person
Jun 23 - Jun 30
found 1 day ago
Roundtrip flight included
Montreal Metropolitan Airport (YHU) to Miami (MIA)
8/10 Very Good! (1 review)
Family Pool Home by Hollywood Beach

Family Pool Home by Hollywood Beach

2.5 out of 5
Hollywood Hills
Price was CA $2,467, price is now CA $1,288 per person
CA $1,288
per person
Jun 26 - Jul 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
No reviews
The Crosby Miami World Center

The Crosby Miami World Center

4 out of 5
Downtown Miami
Price was CA $5,922, price is now CA $3,464 per person
CA $3,464
per person
Jun 23 - Jun 30
found 1 day ago
Roundtrip flight included
Montreal Metropolitan Airport (YHU) to Miami (MIA)
8.4/10 Very Good! (174 reviews)
The property is in one of the many half-empty towers in the center. The location was convenient. There were two reception desks and it was not clear how many agencies and services were renting apartments there. The apartment was spacious, had a washer and a drier, a serviceable kitchen and the elevators worked well.

Reviewed on May 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

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.

Find hotels in South Beach

Westchester Hotel Deals

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
4441 Collins Avenue Miami Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $444 per night from May 26 to May 27
CA $444
CA $599 total
May 26 - May 27
includes taxes & fees
8.4/10 Very Good! (8,225 reviews)
Great stay

Reviewed on May 17, 2026

Fontainebleau Miami Beach
Loews Miami Beach Hotel – South Beach

Loews Miami Beach Hotel – South Beach

4.5 out of 5
1601 Collins Ave Miami Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $274 per night from Jun 4 to Jun 5
CA $274
CA $389 total
Jun 4 - Jun 5
includes taxes & fees
9.2/10 Wonderful! (521 reviews)
Room was clean. Staff was super helpful and friendly. Room was super clean.

Reviewed on May 17, 2026

Loews Miami Beach Hotel – South Beach
Gale Miami Hotel and Residences

Gale Miami Hotel and Residences

4 out of 5
159 NE 6th St Miami FL
Fully refundableReserve now, pay when you stay
The price is CA $211 per night from Jun 9 to Jun 10
CA $211
CA $292 total
Jun 9 - Jun 10
includes taxes & fees
8.8/10 Excellent! (1,869 reviews)
my second time & i’ll always go back here

Reviewed on May 16, 2026

Gale Miami Hotel and Residences
See all 13,273 properties in 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Westchester vacation package cost?
Live it up in Westchester from as low as CA $1,115. 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.

Discover the most popular places to visit in Westchester

Port of Miami Wide

Port of Miami

4.5/5(1,234 reviews)

Explore the waterfront in Miami Beach with a trip to Port of Miami. Amble around this vibrant area's beautiful beaches and enjoy its top-notch restaurants.

Port of Miami
Miami Gardens, USA - 23 February 2026: Aerial view of Hard Rock Stadium bathed in the warm glow of a setting sun, its sleek architecture contrasting with the surrounding lush greenery.

Hard Rock Stadium

4/5(172 reviews)

Catch an event at Hard Rock Stadium during your trip to Miami Gardens. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Hard Rock Stadium
Ocean Drive

Ocean Drive

4.5/5(1,105 reviews)

Miami’s famous strip is not only a gathering point for partiers but well worth the visit for lovers of 1920s art deco architecture.

Ocean Drive

Things to do

Double decker bus in Miami at night

Miami Big Bus Panoramic Night Tour

CA $39
per adult
88% of travellers recommend
Miami Big Bus Panoramic Night Tour
Bimini Bahamas Day Cruise!!

Bahamas Day Cruise with Hotel Pickup

CA $326
per adult
76% of travellers recommend
Bahamas Day Cruise with Hotel Pickup
Thriller Speedboat Ride

Thrilling Speedboat + Sightseeing Tour of Miami

CA $71
per adult
94% of travellers recommend
Thrilling Speedboat + Sightseeing Tour of Miami
See all activities in Miami
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.