Westchester Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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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.
Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
8.2/10 Very Good! (906 reviews)
Everything was perfect. Truly a 5 star hotel. Beach service was very welcomed and done perfectly.

Reviewed on Aug. 3, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1 review)
Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
per person
Oct 25 - Oct 31
found 3 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.6/10 Excellent! (1,154 reviews)
The food options weren’t the best. Very pricey and not many options. The beds were very comfy though.

Reviewed on Aug. 3, 2025

Aloha Fridays

Aloha Fridays

3 out of 5
South Beach
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8.4/10 Very Good! (38 reviews)
Friendly and kind staff. (that was the highlight) Nice room. Great location.

Reviewed on Jul. 26, 2025

The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.4/10 Exceptional! (8 reviews)
Stayed at the new Shelbourne Hotel in Miami Beach and honestly everything was great. The front desk staff was super friendly and helpful, which set the tone right away. The pool was calm and peaceful—such a nice vibe. Everything felt fresh and clean. Definitely would come back.

Reviewed on Jul. 31, 2025

Where to stay in Westchester

Find the best Westchester areas and neighborhoods for the activities you enjoy most. Learn more about Westchester
South Beach showing landscape views, swimming and a sandy beach

South Beach

2 out of top 10 points of interest in this area
4.5/5(1,171 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 $383 per night from Sep 1 to Sep 2
CA $383
CA $520 total
Sep 1 - Sep 2
includes taxes & fees
8/10 Very Good! (6,697 reviews)
"everything was amazing!"

Reviewed on Aug. 2, 2025

Fontainebleau Miami Beach
Kimpton EPIC Hotel by IHG

Kimpton EPIC Hotel by IHG

5 out of 5
270 Biscayne Blvd Way, Miami, FL
Fully refundableReserve now, pay when you stay
The price is CA $226 per night from Aug 19 to Aug 20
CA $226
CA $317 total
Aug 19 - Aug 20
includes taxes & fees
8.8/10 Excellent! (1,959 reviews)
"The Epic hotel was just that, EPIC!! Only downfall would be the food n drinks they have in the room. One of the $10 waters was open and I did everything to make sure I wasn’t charged. Other than that the stay was amazing, room, pool, food , bar and staff all amazing"

Reviewed on Aug. 2, 2025

Kimpton EPIC Hotel by IHG
Mondrian South Beach

Mondrian South Beach

4.5 out of 5
1100 West Ave, Miami Beach, FL
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from Sep 2 to Sep 3
CA $233
CA $336 total
Sep 2 - Sep 3
includes taxes & fees
7.8/10 Good! (2,314 reviews)
"Great"

Reviewed on Aug. 2, 2025

Mondrian South Beach
See all 13,037 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 $471. 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.

Things to do

Miami Skyline Evening Cruise on Biscayne Bay

Miami Skyline Evening Cruise of Biscayne Bay on luxury yacht

CA $31
per adult
Miami Skyline Evening Cruise of Biscayne Bay on luxury yacht
Thriller Speedboat Ride

Thrilling Speedboat + Sightseeing Tour of Miami

CA $62
per adult
94% of travellers recommend
Thrilling Speedboat + Sightseeing Tour of Miami
Miami Skyline Cruise of Millionaire's Homes and Biscayne Bay

Miami Skyline Cruise of Millionaire's Homes with A/C

CA $34
per adult
Miami Skyline Cruise of Millionaire's Homes with A/C
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.