Westchester Holidays from NZ$2,791

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Top Holiday Package Deals in Westchester

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was NZ$4,242, price is now NZ$2,791 per person
NZ$2,791
per person
19 Feb - 23 Feb
found 9 hours ago
Return direct flight included
Auckland (AKL) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Main road in front of hotel was closed. When we arrived, the concierge had no idea where to tell us to park. If they were transparent about it, ok. I would be ok. Then they said they are out of the 'free' wine, but could charge me $8 for a Heineken. Then couldn't get the elevator to work (we were on the 2nd floor thank God) The room was in good shape. The parking is what set off the chain for me. It's not hard to update a website. Or at least tell your staff what to say. Ended up parking in the City parking garage. I'd give it like a 75/100.

Reviewed on 6 Jan 2026

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 NZ$37,372, price is now NZ$19,614 per person
NZ$19,614
per person
19 Feb - 23 Feb
found 9 hours ago
Return direct flight included
Auckland (AKL) to Miami (MIA)
8/10 Very Good! (1 review)
The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Save 100% on your flight
Price was NZ$6,278, price is now NZ$4,023 per person
NZ$4,023
per person
19 Feb - 23 Feb
found 9 hours ago
Return direct flight included
Auckland (AKL) to Miami (MIA)
9.4/10 Exceptional! (56 reviews)
The holding fee is ridiculously high

Reviewed on 8 Jan 2026

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was NZ$4,172, price is now NZ$2,914 per person
NZ$2,914
per person
19 Feb - 23 Feb
found 9 hours ago
Return direct flight included
Auckland (AKL) to Miami (MIA)
8.2/10 Very Good! (1,491 reviews)
Very nice staff, helpful. The only thing is you have to walk through the back alley to go to breakfast. Lol. But rather than that we enjoyed it very much! Will recommend to friends and family!

Reviewed on 9 Jan 2026

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was NZ$3,911, price is now NZ$2,795 per person
NZ$2,795
per person
19 Feb - 23 Feb
found 9 hours ago
Return direct flight included
Auckland (AKL) to Miami (MIA)
8.4/10 Very Good! (1,775 reviews)
Overall is nice. However, i think it will be even better if there is toothbrush and paste

Reviewed on 8 Jan 2026

Our guide on 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 swimming, skyline and a sandy beach

South Beach

2 out of top 10 points of interest in this area
4.5/5(90 area reviews)

Party with the rich and famous in possibly the most glamorous ocean-front setting.

Find hotels in South Beach

Our pick of the best 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 NZ$1,281 per night from 14 Jan to 15 Jan
NZ$1,281
14 Jan - 15 Jan
includes taxes & fees
8.2/10 Very Good! (7,581 reviews)
Nice

Reviewed on 5 Jan 2026

Fontainebleau Miami Beach
Park Central South Beach

Park Central South Beach

4 out of 5
640 Ocean Dr Miami Beach FL
Fully refundableReserve now, pay when you stay
The price is NZ$417 per night from 14 Jan to 15 Jan
NZ$417
14 Jan - 15 Jan
includes taxes & fees
8.6/10 Excellent! (612 reviews)
Great amenities.

Reviewed on 6 Jan 2026

Park Central South Beach
Hilton Miami Airport Blue Lagoon

Hilton Miami Airport Blue Lagoon

4 out of 5
5101 Blue Lagoon Dr Miami FL
Fully refundableReserve now, pay when you stay
The price is NZ$371 per night from 10 Feb to 11 Feb
NZ$371
10 Feb - 11 Feb
includes taxes & fees
8/10 Very Good! (3,767 reviews)
The grounds are gorgeous outside but the rooms could use some updates

Reviewed on 5 Jan 2026

Hilton Miami Airport Blue Lagoon
See all 12,302 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.

Frequently asked questions

How much does a Westchester holiday package cost?
Live it up in Westchester from as low as NZ$2,791. 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 holiday 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 holiday 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 holiday?
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 holiday 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 holiday package?
Whether it's your hotel, flight or rental car, you can cancel or amend it. Booked your Westchester holiday 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

Coral Way Shopping Area

During your trip to Miami, you can find the perfect gifts to bring home at Coral Way Shopping Area. While you're in the area, stroll along the beaches.

Coral Way Shopping Area

Activities

Official Miami Millionaires Sightseeing Cruise

Miami Millionaires Sightseeing Cruise

NZ$31
per adult
92% of travellers recommend
Miami Millionaires Sightseeing Cruise
Everglades Adventure Tour From Miami in a Luxury Bus

Everglades Adventure with Airboat

NZ$105
per adult
88% of travellers recommend
Everglades Adventure with Airboat
Little Havana Food and Walking Tour in Miami

Little Havana Food and Walking Tour in Miami

NZ$121
per adult
98% of travellers recommend
Little Havana Food and Walking Tour in 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.