Westchester Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

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

    Plan, book, and manage your trip all in one place

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.
Soleado Hotel

Soleado Hotel

3 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Sep 16 - Sep 23
just found
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (609 reviews)
Very Clean and Quiet Area.. Walking Distance From the Beach..

Reviewed on Jun. 29, 2025

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
Sep 16 - Sep 23
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.6/10 Excellent! (1,119 reviews)
We have been here multiple time and we love this hotel, the staff is nice and friendly, the food is good, the rooms are clean and have plenty of space The hotel is close to many restaurants in the area, the small lazy river in the pool area is great for kids. I recommend this hotel.

Reviewed on Jul. 13, 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
Save 100% on your flight
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
9.6/10 Exceptional! (5 reviews)
Wonderful hotel. Beautiful design and very attentive staff.

Reviewed on Jul. 7, 2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
9.4/10 Exceptional! (1,212 reviews)
Great hotel. Very expensive food and drinks (£25 for two coffees and croissant) and the gym staff were miserable BUT other staff were great and the pool / beach / room were excellent. We had problems with our bathroom but to be honest I’d still recommend the hotel.

Reviewed on Jul. 13, 2025

iCoconutGrove Vacation Rentals

iCoconutGrove Vacation Rentals

4 out of 5
Coconut Grove
Save 100% on your flight
per person
Sep 26 - Sep 30
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
9.2/10 Wonderful! (1,000 reviews)
The property was in a very populated area with lots of shops, restaurants and nightlife (if that’s your thing). The studio was very clean and there were no issues at all. Unlike hotel rooms, I could not hear what was happening right next door, so it was quiet as well. I would stay here again.

Reviewed on Jul. 12, 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 featuring skyline, 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 $421 per night from Jul 15 to Jul 16
CA $421
CA $563 total
Jul 15 - Jul 16
includes taxes & fees
8/10 Very Good! (6,548 reviews)
"Excellent"

Reviewed on Jul. 13, 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 $215 per night from Aug 14 to Aug 15
CA $215
CA $305 total
Aug 14 - Aug 15
includes taxes & fees
8.8/10 Excellent! (1,885 reviews)
"Amazing setup, pool vibes were it if your visiting! Room was spacious and clean"

Reviewed on Jul. 11, 2025

Kimpton EPIC Hotel by IHG
citizenM Miami Worldcenter
citizenM Miami Worldcenter
4 out of 5
700 NE 2ND AVENUE, Miami, FL
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Aug 11 to Aug 12
CA $155
CA $175 total
Aug 11 - Aug 12
includes taxes & fees
9.2/10 Wonderful! (4,724 reviews)
"Five Star Hotel"

Reviewed on Jul. 13, 2025

citizenM Miami Worldcenter
See all 12,954 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 $663. 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

Bimini Bahamas Day Cruise!!

Bahamas Day Cruise with Hotel Pickup

CA $364
per adult
Bahamas Day Cruise with Hotel Pickup
Miami: 1-hour Jetcar Rental

Miami: 1-hour Jetcar Rental

CA $69
per traveller
80% of travellers recommend
Miami: 1-hour Jetcar Rental
Miami Skyline Evening Cruise on Biscayne Bay

Miami Skyline Evening Cruise of Biscayne Bay on luxury yacht

CA $36
per adult
Miami Skyline Evening Cruise of Biscayne Bay on luxury yacht
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.