Title: Westchester Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $1,035 Expedia.ca

[Hotels in Westchester](https://expedia.ca/Westchester-Miami-Hotels.0-n553248635975847513-0.Travel-Guide-Filter-Hotels)[Flights to Miami](https://expedia.ca/Cheap-Flights-To-Miami.d178286.Travel-Guide-Flights)[Things to do in Miami](https://expedia.ca/Things-To-Do-In-Miami.d178286.Travel-Guide-Activities)[Westchester Car Rentals](https://expedia.ca/Car-Rentals-In-Westchester.d553248635975847513.Car-Rental-Guide)

![](https://images.trvl-media.com/place/553248635975847513/fdcd9690-9621-47e7-a497-ccb76e4ed81f.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Westchester Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
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](https://www.expedia.ca/University-Of-Miami-Miami.d501784.Vacation-Attraction), [Dadeland Mall](https://www.expedia.ca/Dadeland-Mall-Kendall.d6127764.Vacation-Attraction) and [Miracle Mile](https://www.expedia.ca/Miracle-Mile-Coral-Gables-Section.d6127766.Vacation-Attraction), 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.

![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/4743fa46_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Creekside Inn

CA $1,035

per person

May 28 - Jun 2

found 6 hours ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

7.8/10 Good! (1,007 reviews)

Room did not have a water view as was listed on the site, pool was cold but clean. Staff was friendly and helpful.

Reviewed on Mar 4, 2026

![Casablanca Miami Beach](https://images.trvl-media.com/lodging/32000000/31660000/31652200/31652150/f54c02bb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Casablanca Miami Beach

North Beach

CA $2,401

per person

May 23 - May 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

5.8/10 (320 reviews)

Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.

Reviewed on Feb 22, 2026

![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/e518a34f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

CA $12,160

per person

Apr 26 - May 1

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Miami (MIA)

8/10 Very Good! (1 review)

![Cavalier Hotel South Beach](https://images.trvl-media.com/lodging/1000000/20000/13600/13579/c0c3faa8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cavalier Hotel South Beach

South Beach

CA $1,059

per person

Apr 26 - May 1

found 1 day ago

Roundtrip flight included

Hamilton (YHM) to Miami (MIA)

8.6/10 Excellent! (1,002 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 Feb 24, 2026

![President Hotel Villa](https://images.trvl-media.com/lodging/11000000/10620000/10612900/10612810/5a873fda_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### President Hotel Villa

South Beach

CA $1,158

per person

May 23 - May 30

found 1 day ago

Roundtrip flight included

Montreal Metropolitan Airport (YHU) to Miami (MIA)

8.2/10 Very Good! (1,007 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 Mar 3, 2026

## Where to stay in Westchester

Find the best Westchester areas and neighborhoods for the activities you enjoy most. [Learn more about Westchester](https://expedia.ca/Miami-Westchester.dx553248635975847513)

![South Beach showing landscape views, swimming and a sandy beach](https://images.trvl-media.com/place/6138745/4bcc758d-292d-4949-a829-348fc2278cf4.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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 hotel + flight trips in South Beach](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=South%20Beach&DestID=6138745&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Miami, Florida, USA - Jan 2016: Luxurious condominiums and hi-rises, and beautiful palm trees in Brickell Bay Drive.](https://images.trvl-media.com/place/6240961/aec623b9-5246-42dd-b100-c3b9c59ccc6f.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Brickell

1 out of top 10 points of interest in this area

4/5(8 area reviews)

 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. 

[Find hotel + flight trips in Brickell](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Brickell&DestID=6240961&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Downtown Miami which includes night scenes, a city and a river or creek](https://images.trvl-media.com/place/800070/9ea993d5-24cb-4fcb-86e9-ced4d9090113.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Downtown Miami

1 out of top 10 points of interest in this area

4/5(331 area reviews)

 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. 

[Find hotel + flight trips in Downtown Miami](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Miami&DestID=800070&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Shot from the Palmetto expressway. ](https://images.trvl-media.com/place/6060126/857e4433-a55e-48a9-90fa-a8a304234b89.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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. 

[Find hotel + flight trips in Doral](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Doral&DestID=6060126&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![EyeEm Custom Shoots Q4 2018](https://images.trvl-media.com/place/553248635975724424/32ed8d47-bdba-4f42-8111-682021553d6c.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Flamingo/Lummus

 If you're spending some time in Flamingo/Lummus, Collins Avenue Shopping Area and The Wolfsonian Museum are top sights worth seeing. 

[Find hotel + flight trips in Flamingo/Lummus](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Flamingo/Lummus&DestID=553248635975724424&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Westchester Hotel Deals

![Fontainebleau Miami Beach](https://images.trvl-media.com/lodging/2000000/1200000/1190600/1190549/4c5e4651_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Fontainebleau Miami Beach

4441 Collins Avenue Miami Beach FL

Fully refundableReserve now, pay when you stay

CA $442

CA $596 total

Mar 8 - Mar 9

includes taxes & fees

8.4/10 Very Good! (7,948 reviews)

Good hotel, but they charge a kot more than the stay, and till now not sorred out, they charged me above 4,000 usd for a 2500 usd stay !

Reviewed on Mar 3, 2026

[](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=1190549&PinnedHotelID=1190549&HadPinnedHotel=true&regionId=553248635975847513)

![Kompose Boutique Hotel Miami Airport ](https://images.trvl-media.com/lodging/112000000/111900000/111893500/111893452/5069ea21_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Kompose Boutique Hotel Miami Airport 

3401 NW 25th St Miami FL

CA $153

CA $190 total

Mar 23 - Mar 24

includes taxes & fees

9/10 Wonderful! (2,867 reviews)

Hotel was cleaned and the staff were so nice. We had an early flight and they let us check in early. Would definitely recommend this hotel.

Reviewed on Mar 4, 2026

[](https://expedia.ca/Hotel-Search?startDate=23%2F03%2F2026&endDate=24%2F03%2F2026&selected=111893452&PinnedHotelID=111893452&HadPinnedHotel=true&regionId=553248635975847513)

![Loews Miami Beach Hotel – South Beach](https://images.trvl-media.com/lodging/1000000/90000/81300/81223/2665e91b_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Loews Miami Beach Hotel – South Beach

1601 Collins Ave Miami Beach FL

Fully refundableReserve now, pay when you stay

CA $585

CA $736 total

Mar 22 - Mar 23

includes taxes & fees

9.2/10 Wonderful! (214 reviews)

Beach View

Reviewed on Mar 5, 2026

[](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=81223&PinnedHotelID=81223&HadPinnedHotel=true&regionId=553248635975847513)

[See all 12,407 properties in Westchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=06%2F03%2F2026&endDate=07%2F03%2F2026&regionId=553248635975847513)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## Frequently asked questions

### How much does a Westchester vacation package cost?

### How do I get a cheap travel package to Westchester?

### Where should I stay in Westchester?

### What are the top hotels in Westchester?

### How far in advance should I book my Westchester vacation?

### What does an Expedia Westchester travel package include?

### What should I know before booking a Westchester travel package?

### Can I choose my airline with a Westchester Expedia vacation package?

### If I'm not able to travel, can I cancel my Westchester vacation package?

### Things to do

![ Round-trip Transportation to Key West from Miami](https://mediaim.expedia.com/localexpert/2088061/2d239d7a-6886-4e7d-bee2-f3bb8bcc5eb3.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

####  Round-trip Transportation to Key West from Miami

CA $103

per adult

[](https://expedia.ca/things-to-do/round-trip-transportation-to-key-west-from-miami.a2088061.activity-details)

![Thriller Speedboat Ride](https://mediaim.expedia.com/localexpert/336754/a6eaadcd-4714-47f5-b559-96fd89e9c77c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Thrilling Speedboat + Sightseeing Tour of Miami

CA $62

per adult

**94%** of travellers recommend

[](https://expedia.ca/things-to-do/thrilling-speedboat-sightseeing-tour-of-miami.a336754.activity-details)

![Miami: Off-Road ATV Guided Tour](https://mediaim.expedia.com/localexpert/48221160/5c716ff3-3cfb-47bb-88d4-e5a620aaeae8.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Miami: Off-Road ATV Guided Tour

CA $21

per adult

**80%** of travellers recommend

[](https://expedia.ca/things-to-do/miami-off-road-atv-guided-tour.a48221160.activity-details)

[See all activities in Miami](https://expedia.ca/things-to-do/search?rid=553248635975847513)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.