Westchester Vacations from $776

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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.

The Latest Westchester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Le Particulier Miami

Le Particulier Miami

3.5 out of 5
Mid Beach
Price was $1,966, price is now $776 per person
$776
per person
Feb 10 - Feb 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
10/10 Exceptional! (1 review)
Room was nice. Building was a little dated. Very small elevator especially because it was the only one. Staff was very nice and the front area was great. Nice location. Price was a little high.

Reviewed on Nov 23, 2025

Bay Breeze Premium Apartments By Eskape Collection

Bay Breeze Premium Apartments By Eskape Collection

4 out of 5
Price was $2,506, price is now $998 per person
$998
per person
Feb 10 - Feb 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (189 reviews)
Will be nice if the hotel can think about what a new hotel guest will be going through. They will usually drive up to the hotel and look for parking. Then they will look into how to check-in and how to get to their room. It will be nice to mention in the welcome text to fill out the registration and the credit card authorization, AND also mention if we have a vehicle, what shall we do. Also will be helpful if the text will let us know the office in the building will be closed on Saturdays (and Sundays?) We were trying to figure all these out while carrying our luggages under strong winds, lucky it didn't rain. Will also be helpful to text us that we need to submit those 2 forms, then we will receive our gate and door codes. Restroom didn't smell fresh. Other than the aforementioned, the stay was good.

Reviewed on Oct 27, 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
Price was $2,084, price is now $929 per person
$929
per person
Feb 22 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (56 reviews)
Breakfast was good, but not great. Hotel beautifully designed. Champagne upon arrival. Family friendly

Reviewed on Nov 25, 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
Price was $12,713, price is now $5,696 per person
$5,696
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Price was $2,092, price is now $943 per person
$943
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (829 reviews)
Rooms were clean and the staff were good as well.

Reviewed on Nov 19, 2025

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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, swimming and a sandy beach

South Beach

3 out of top 10 points of interest in this area
4.5/5(11,595 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
$466 nightly
The price is $531 total per night from Dec 10 to Dec 11
$531 total
Dec 10 - Dec 11
Total with taxes and fees
8.2/10 Very Good! (7,372 reviews)
Ocean Fromt view was amazing…

Reviewed on Nov 24, 2025

Fontainebleau Miami Beach
Hyatt Regency Miami

Hyatt Regency Miami

4 out of 5
400 Se 2nd Ave Miami FL
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $180 total per night from Dec 15 to Dec 16
$180 total
Dec 15 - Dec 16
Total with taxes and fees
8.6/10 Excellent! (2,140 reviews)
Room was clean, staff was super friendly, only small issue I had previously gotten a late checkout for 12pm and we came back to room from breakfast at 11:20 and our keys didn’t work. Whoever changed my checkout or ok it, didn’t change it in their system.

Reviewed on Nov 23, 2025

Hyatt Regency Miami
citizenM Miami Worldcenter

citizenM Miami Worldcenter

4 out of 5
700 NE 2ND AVENUE Miami FL
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $121 total per night from Dec 15 to Dec 16
$121 total
Dec 15 - Dec 16
Total with taxes and fees
9.2/10 Wonderful! (5,759 reviews)
Location

Reviewed on Nov 24, 2025

citizenM Miami Worldcenter
See all 12,746 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
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Discover the most popular places to visit in Westchester

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 Way Shopping Area

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.

Coral Estates Park

Things to do

Official Miami Millionaires Sightseeing Cruise

Miami Millionaires Sightseeing Cruise

$18
per adult
88% of travellers recommend
Miami Millionaires Sightseeing Cruise
Miami Skyline Cruise of Millionaire's Homes and Biscayne Bay

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

$28
per adult
Miami Skyline Cruise of Millionaire's Homes with A/C
Three people parasailing in Miami

Parasail with Miami Watersports

$68
per adult
86% of travellers recommend
Parasail with Miami Watersports
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.