Title: Windward Side Vacation Packages & Trips 2026 from CA $1,470 | Expedia.ca

[Hotels in Windward Side](https://expedia.ca/Windward-Side-Hotels.d11638.Travel-Guide-Hotels)[Vacation Rentals in Windward Side](https://expedia.ca/Windward-Side-Vacation-Rentals.d11638.Travel-Guide-VacationRentals)[Things to do in Windward Side](https://expedia.ca/Things-To-Do-In-Windward-Side.d11638.Travel-Guide-Activities)[Windward Side Car Rentals](https://expedia.ca/Car-Rentals-In-Windward-Side.d11638.Car-Rental-Guide)

![](https://images.trvl-media.com/place/11638/a9b7423c-b482-4cbc-b1e7-ef03e6886cb5.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Windward Side 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 Windward Side Vacation

Our Windward Side vacation packages give you the power to create your own adventure. Tailor your journey to suit your needs and interests and make every moment count in this wonderful city. Make your trip to Windward Side even more fun by going sightseeing. [Wells Bay Beach](https://www.expedia.ca/Wells-Bay-Beach-Saba.d6114428.Vacation-Attraction), [Cove Bay Beach](https://www.expedia.ca/Cove-Bay-Beach-Saba.d553248621584952177.Vacation-Attraction) and [Dutch Museum of Saba](https://www.expedia.ca/Dutch-Museum-Of-Saba-Saba.d553248621584952178.Vacation-Attraction) are some of the major attractions you'll want to explore. Whoever you're going away with and whatever the size of your budget, your dream Windward Side vacation is just clicks away with Expedia.

## Top Windward Side Vacation Deals

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

![El Momo Cottages](https://images.trvl-media.com/lodging/12000000/11950000/11944600/11944556/33fcc0f7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### El Momo Cottages

CA $1,470

per person

Mar 22 - Mar 29

found 1 hour ago

Roundtrip flight included

Toronto (YTO) to Saba (SAB)

8.6/10 Excellent! (54 reviews)

Was exactly as described, remote location with lots of stairs - well worth the walk, scenery was beautiful.

Reviewed on Jul 20, 2025

## Ready to book your vacation to Windward Side?

Choose your dates

## Windward Side Hotel Deals

![Saba Arawak Hotel](https://images.trvl-media.com/lodging/74000000/73670000/73660700/73660604/738de9aa_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Saba Arawak Hotel

The peak Windward Side Saba

8.4/10 Very Good! (79 reviews)

Friendly Staff

Reviewed on Jan 7, 2026

[Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=73660604&PinnedHotelID=73660604&HadPinnedHotel=true&regionId=11638)

[](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=73660604&PinnedHotelID=73660604&HadPinnedHotel=true&regionId=11638)

![El Momo Cottages](https://images.trvl-media.com/lodging/12000000/11950000/11944600/11944556/33fcc0f7_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

El Momo Cottages

Booby Hill Windward Side Saba

CA $153

CA $164 total

Feb 14 - Feb 15

includes taxes & fees

8.4/10 Very Good! (54 reviews)

The staff is fantastic! Cabins are simple, clean and comfortable. Breakfast was delicious.The views are amazing! Be prepared to climb to enjoy the views. Lots of stairs but worth it!

Reviewed on Nov 21, 2025

[](https://expedia.ca/Hotel-Search?startDate=14%2F02%2F2026&endDate=15%2F02%2F2026&selected=11944556&PinnedHotelID=11944556&HadPinnedHotel=true&regionId=11638)

![Flamboyant Cottage - Spectacular View & Pool](https://images.trvl-media.com/lodging/35000000/34010000/34006200/34006194/3c3130af_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Flamboyant Cottage - Spectacular View & Pool

 Windward Side Saba

9.6/10 Exceptional! (33 reviews)

Lovely cabin with incredible view.

Reviewed on Dec 19, 2025

[Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=34006194&PinnedHotelID=34006194&HadPinnedHotel=true&regionId=11638)

[](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=34006194&PinnedHotelID=34006194&HadPinnedHotel=true&regionId=11638)

[See all 27 properties in Windward Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&regionId=11638)

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)

### What to do in Windward Side

![Edge Ferry to Saba](https://mediaim.expedia.com/localexpert/253604/6fc90e0a-d2d4-4d4b-ad5d-86cb5d90f28c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Edge Ferry Tickets to Saba

CA $139

per adult

**78%** of travellers recommend

[](https://expedia.ca/things-to-do/edge-ferry-tickets-to-saba.a253604.activity-details)

![The Beauty of Fresh Lake Naivasha with some Cormorants Flying.](https://mediaim.expedia.com/localexpert/3421676/f8c19994-bd1e-40b1-9dd8-90b719267d98.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 5 Days Safari to Lake Naivasha, Hells Gate N/P, Maasai Mara N/R.

CA $1,597

per adult

[](https://expedia.ca/things-to-do/5-days-safari-to-lake-naivasha.a3421676.activity-details)

[See all activities in Windward Side](https://expedia.ca/things-to-do/search?rid=11638)

## Explore a world of travel with Expedia

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

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app