Westchester Holidays

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    Save up to €185 when you book a flight and hotel together*

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

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Price found within the past 48 hours. Click for updated prices.
The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was €635, price is now €357 per person
€357
per person
5 May - 9 May
found 1 day ago
Return flight included
New York (JFK) to Miami (MIA)
8.2/10 Very Good! (1,491 reviews)
Right across the street from the beach!

Reviewed on 2 Mar 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 €12,928, price is now €6,381 per person
€6,381
per person
5 May - 9 May
found 1 day ago
Return flight included
New York (JFK) to Miami (MIA)
8/10 Very Good! (1 review)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was €842, price is now €437 per person
€437
per person
5 May - 9 May
found 1 day ago
Return flight included
New York (JFK) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Loved the location, room was nice, bathroom very small, very friendly staff, slow service at restaurant in the morning. Will go back

Reviewed on 24 Feb 2026

President Hotel Villa

President Hotel Villa

3.5 out of 5
South Beach
Price was €751, price is now €410 per person
€410
per person
5 May - 9 May
found 1 day ago
Return flight included
New York (JFK) to Miami (MIA)
8.2/10 Very Good! (997 reviews)
Mike and Henry were extremely helpful with directions, valet service assistance, and any questions were answers, making it a very pleasant experience!

Reviewed on 3 Mar 2026

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was €751, price is now €410 per person
€410
per person
5 May - 9 May
found 1 day ago
Return flight included
New York (JFK) to Miami (MIA)
8.4/10 Very Good! (1,775 reviews)
I really liked the location — it was very convenient. The room was pretty big and very clean, which made the stay comfortable. The staff was friendly and welcoming. The breakfast was okay, nothing special, but it was fine.

Reviewed on 1 Mar 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 featuring skyline, landscape views and a sandy beach

South Beach

2 out of top 10 points of interest in this area
4.5/5(411 area reviews)

Sunbathe, shop, people-watch, or party with the stars at one of Miami’s most famous beach promenades, also regarded as the art deco capital of the world.

Find hotels in South Beach

Top hotels in Westchester

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
4441 Collins Avenue Miami Beach FL
Fully refundableReserve now, pay when you stay
8.4/10 Very Good! (7,943 reviews)
Great stay, beautiful pool, beach view was unobstructed. lovely amenities. Traveled with family two boys 11 and 14. We did water sports, used the bikes, and enjoyed the resort.

Reviewed on 3 Mar 2026

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Fontainebleau Miami Beach
Kompose Boutique Hotel Miami Airport

Kompose Boutique Hotel Miami Airport

3 out of 5
3401 NW 25th St Miami FL
The price is €116 per night from 23 Mar to 24 Mar
€116
23 Mar - 24 Mar
includes taxes & fees
9/10 Wonderful! (2,854 reviews)
The great hotel I ever been to it

Reviewed on 3 Mar 2026

Kompose Boutique Hotel Miami Airport
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 €495 per night from 11 Mar to 12 Mar
€495
11 Mar - 12 Mar
includes taxes & fees
9/10 Wonderful! (4,886 reviews)
Great room, incredible staff, nice pool and shops.

Reviewed on 2 Mar 2026

Loews Miami Beach Hotel – South Beach
See all 12,407 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 €357. 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.

Popular places to visit

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

Things to do

Official Miami Millionaires Sightseeing Cruise

Miami Millionaires Sightseeing Cruise

€15
per adult
92% of travellers recommend
Miami Millionaires Sightseeing Cruise
Round-trip Transportation to Key West from Miami

Round-trip Transportation to Key West from Miami

€63
per adult
Round-trip Transportation to Key West from Miami
Everglades Adventure Tour From Miami in a Luxury Bus

Everglades Adventure with Airboat

€51
per adult
88% of travellers recommend
Everglades Adventure with Airboat
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.