Westchester Vacation Packages 2026 from $672

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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.

President Hotel Villa

South Beach

Save 100% on your flight

$672

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,004 reviews)

I love the room. I would definitely stay again. The only thing I would say is the showers are definitely not hot enough for me. I don’t know if I just like it too hot but that’s the only issue I really had.

Reviewed on Sep 7, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,270

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

Miami Vacation Rentals - Brickell

Brickell

$1,319

per person

Dec 2 - Dec 7

found 1 day ago

Roundtrip non-stop flight included

Philadelphia (PHL) to Miami (MIA)

8.8/10 Excellent! (567 reviews)

Is a very nice property. SPA and Gym are very good. Very clean rooms with everything you need to make an apartment work (cleaning products, toiletries). The only bad thing was that the pool is closed an it will probably be by the entire year, they compensated with free wine and activites.

Reviewed on Sep 14, 2026

Miami Vacation Rentals - Downtown

Downtown Miami

$1,053

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9/10 Wonderful! (83 reviews)

You get what you buy easy and smooth

Reviewed on Sep 18, 2026

The Local House

South Beach

Save 100% on your flight

$905

per person

Nov 10 - Nov 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (1,001 reviews)

Where to stay in Westchester

Find the best Westchester areas and neighborhoods for the activities you enjoy most. Learn more about Westchester

A beach with clear turquoise water, a rocky shoreline, and several high-rise buildings in the background.

South Beach

3 out of top 10 points of interest in this area

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.

A coastal cityscape with high-rise buildings and a marina.

Brickell

A dense, high-rise residential area with upscale condos, Brickell boasts popular Miami restaurants, shops, and art galleries. Explore Mary Brickell Village or catch the Metromover for easy transportation.

A city skyline at dusk with illuminated buildings reflecting on the water.

Downtown Miami

2 out of top 10 points of interest in this area

An urban city center with a rich cultural scene, Downtown Miami offers shopping at Flagler Street, Bayside Marketplace, and Mary Brickell Village. Explore Pérez Art Museum Miami, Miami Children's Museum, and enjoy the pedestrian-friendly area with extensive public transit options.

A modern urban area with two prominent high-rise buildings, a central road, and surrounding commercial buildings.

Doral

A noteworthy feature of Doral is its popular shops. While you're in town, be sure to stop and check out CityPlace Doral and Miami International Mall.

A street with palm trees, cars, and a pedestrian crossing sign.

Flamingo/Lummus

If you're spending some time in Flamingo/Lummus, Collins Avenue Shopping Area and Miami Beach Boardwalk are top sights worth seeing.

Westchester Hotel Deals

Fontainebleau Miami Beach

4441 Collins Avenue Miami Beach FL

Fully refundableReserve now, pay when you stay

$296 nightly

$338 total

Sep 20 - Sep 21

Total with taxes and fees

Loews Miami Beach Hotel – South Beach

1601 Collins Ave Miami Beach FL

Fully refundableReserve now, pay when you stay

$309 nightly

$352 total

Sep 20 - Sep 21

Total with taxes and fees

Miami International Airport Hotel

N.W. 20th & Lejeune Road Miami FL

Fully refundableReserve now, pay when you stay

$178 nightly

$201 total

Sep 21 - Sep 22

Total with taxes and fees

8/10 Very Good! (5,657 reviews)

"N"

Reviewed on Sep 19, 2026

See all 14,133 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.

Stay near popular Westchester attractions

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.

See properties

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.

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Bianco Bistro Cafe

Bianco Bistro Cafe is just one of the places to see in Miami, so why not enjoy the other things to explore during your travels?

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Things to do

Miami Sunset and City Lights Cocktail Cruise with Open Bar

$69

per adult

92% of travellers recommend

Miami: Off-Road ATV Guided Tour

$15

per adult

Thrilling Speedboat + Sightseeing Tour of Miami

$52

per adult

94% of travellers recommend

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.

Westchester Vacations from $672

Book a Hotel + Flight or Car together to unlock savings

Room 1

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Westchester Vacation

The Latest Westchester Vacation Packages

President Hotel Villa

The Retreat Collection at 1 Hotel & Homes South Beach

Miami Vacation Rentals - Brickell

Miami Vacation Rentals - Downtown

The Local House

Where to stay in Westchester

South Beach

Brickell

Downtown Miami

Doral

Flamingo/Lummus

Westchester Hotel Deals

Fontainebleau Miami Beach

Loews Miami Beach Hotel – South Beach

Miami International Airport Hotel

Stay near popular Westchester attractions

Coral Way Shopping Area

Coral Estates Park

Bianco Bistro Cafe

Things to do

Miami Sunset and City Lights Cocktail Cruise with Open Bar

Miami: Off-Road ATV Guided Tour

Thrilling Speedboat + Sightseeing Tour of Miami