---
title: "Windward Side Vacation Packages & Trips 2026 | Expedia"
description: "FREE cancellation on select hotels Bundle Windward Side flight and hotel to build your own Windward Side vacation package & you can 𝘀𝗮𝘃𝗲 with Expedia! Choose from thousands of Windward Side holiday trips & travel deals."
canonical: "https://www.expedia.ca/Windward-Side.d11638.Destination-Travel-Guides"
language: en-CA
market: CA
currency: CAD
prices_as_of: 2026-11-12T17:14:36Z
---

# Windward Side Vacation Packages
![A calm sea with a mountain in the distance.](https://images.trvl-media.com/place/11638/a9b7423c-b482-4cbc-b1e7-ef03e6886cb5.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

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

- ## Plan, book, travel with confidence
- ### Better together
Save up to CA $4,200 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.

## Discover the most popular places to visit in Windward Side

### Dutch Museum of Saba

Rating: 8.4/10 (5 reviews)

You can spend time browsing the exhibits at Dutch Museum of Saba in Windward Side. While you're in the area, wander around the gardens.

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621584952178)

### Saba Heritage Center

You can spend an afternoon studying the exhibits at Saba Heritage Center in Windward Side. Wander the seaside and rainforest while you're in the area.

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=808648223374106624)

### Harry L Johnson Museum

Rating: 8.8/10 (3 reviews)

You can spend an afternoon studying the exhibits at Harry L Johnson Museum in Windward Side. While you're in the area, wander around the gardens.

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621533158269)

### Jo Bean Glass Art Studio

Rating: 9.8/10 (8 reviews)

You can spend an afternoon studying the exhibits at Jo Bean Glass Art Studio in Windward Side. While you're in the area, wander around the gardens.

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621533158270)

### What to do in Windward Side

![5 Days Safari to Lake Naivasha, Hells Gate N/P, Maasai Mara N/R.](https://mediaim.expedia.com/localexpert/3421676/fef41ee7-8864-4396-b6f6-4235aef17d52.jpg?impolicy=resizecrop&rw=1005&rh=565)

#### [5 Days Safari to Lake Naivasha, Hells Gate N/P, Maasai Mara N/R.](https://www.expedia.ca/things-to-do/a.a3421676.activity-details?rid=11638)

CA $1,622

per adult

0% of travellers recommend

![Historic City and Beach E-Bike Tour](https://mediaim.expedia.com/localexpert/3327829/b5e8298c-321f-48e7-95c6-2e75bb8d85bb.jpg?impolicy=resizecrop&rw=1005&rh=565)

#### [Historic City, Fort and Beach E-Bike Tour](https://www.expedia.ca/things-to-do/a.a3327829.activity-details?rid=11638)

CA $184

per adult

100% of travellers recommend

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

## Windward Side Hotel Deals

### [Saba Arawak Hotel](https://www.expedia.ca/Windward-Side-Hotels-Saba-Arawak-Hotel.h73660604.Hotel-Information)

![A rectangular swimming pool with a white tiled deck, surrounded by white railings and lounge chairs.](https://images.trvl-media.com/lodging/74000000/73670000/73660700/73660604/d45b92b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: The peak, Windward Side, Saba, BQ
- Location: 0.2 km from Windward Side
- Star rating: 3/5
- Guest rating: 8.2/10 (Very good, 111 reviews)
- Price: CA $192, CA $225 total, includes taxes & fees, Nov 13 - Nov 14
- Review: Excellent in all ways

### [El Momo Cottages](https://www.expedia.ca/Windward-Side-Hotels-El-Momo-Cottages.h11944556.Hotel-Information)

![A wooden deck with lounge chairs and a table, overlooking a scenic view of the ocean and lush greenery.](https://images.trvl-media.com/lodging/12000000/11950000/11944600/11944556/59c43c6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: Booby Hill, Windward Side, Saba, BQ
- Location: 0.5 km from Windward Side
- Star rating: 3/5
- Guest rating: 8.6/10 (Excellent, 63 reviews)
- Review: "mosquitos you had to climb 80 slippery steps to climb to reach to tiny room they call cottage one night strange voices of man and woman when i was told that only one or two people lived in mosquitoes bites whole body criquet sounds all night /cant sleep to reach toilet at night walk down 4 to 5 slippery steps in rain jungle like environment i was forced to leave after staying 3 nights and flnd better hotel and pay again for rest in Saba till 13 sept i complained to expedia customer...

### [Scenery Hotel Saba](https://www.expedia.ca/Windward-Side-Hotels-The-Scenery-Hotel-Saba.h123169989.Hotel-Information)

![A pool area with lounge chairs, a pergola, and a view of a mountain.](https://images.trvl-media.com/lodging/124000000/123170000/123170000/123169989/ae0cd0ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 9 Fort Street, Windward Side, Saba, BQ
- Location: < 0.1 km from Windward Side
- Star rating: 3.5/5
- Price: CA $389, CA $459 total, includes taxes & fees, Nov 13 - Nov 14

### [Cattleya Flor Hotel](https://www.expedia.ca/Oranjestad-Hotels-Cattleya-Flor-Hotel.h138324069.Hotel-Information)

![A hotel room with a bed, a chair, a table with a vase of flowers, and a mirror on the wall.](https://images.trvl-media.com/lodging/139000000/138330000/138324100/138324069/4a32f90b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: Weg naar Root #10, Oranjestad, Sint Eustatius, BQ
- Location: 30.6 km from Windward Side
- Star rating: 2/5
- Price: CA $147, CA $157 total, includes taxes & fees, Dec 8 - Dec 9

### [The Old Gin House](https://www.expedia.ca/Oranjestad-Hotels-The-Old-Gin-House.h8273394.Hotel-Information)

![A beach with palm trees, a stone wall, and a building in the background.](https://images.trvl-media.com/lodging/9000000/8280000/8273400/8273394/f062af63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: Oranjebaai 1, Oranjestad, Sint Eustatius, BQ
- Location: 30.6 km from Windward Side
- Star rating: 3/5
- Guest rating: 8.4/10 (Very good, 65 reviews)
- Price: CA $226, CA $241 total, includes taxes & fees, Nov 21 - Nov 22

### [Talk of the Town Inn & Suites](https://www.expedia.ca/Oranjestad-Hotels-Talk-Of-The-Town.h32813162.Hotel-Information)

![A cozy room with a high ceiling, large windows, a sofa, two wicker chairs, and a wooden table.](https://images.trvl-media.com/lodging/33000000/32820000/32813200/32813162/ecfb3641.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: L.E. Saddler Road #9, Oranjestad, St. Eustatius, BQ
- Location: 30.5 km from Windward Side
- Star rating: 3/5
- Guest rating: 8.2/10 (Very good, 20 reviews)
- Price: CA $139, CA $149 total, includes taxes & fees, Dec 9 - Dec 10
- Review: The room was nice, clean spacious but did not have a TV . Nice kitchen.The location is good , near the airport

### [Quill Gardens Boutique Hotel](https://www.expedia.ca/Oranjestad-Hotels-Quill-Gardens-Estate.h85534552.Hotel-Information)

![A pathway lined with palm trees and tropical plants, leading to a building with a blue facade.](https://images.trvl-media.com/lodging/86000000/85540000/85534600/85534552/499a6edb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: Road to English Quarter, Oranjestad, Sint Eustatius, BQ
- Location: 31.8 km from Windward Side
- Star rating: 4/5
- Guest rating: 9.6/10 (Exceptional, 32 reviews)
- Price: CA $228, CA $244 total, includes taxes & fees, Dec 5 - Dec 6
- Review: Anton was an excellent host. Best chef in town.

### [Palm Spring Inn](https://www.expedia.ca/Oranjestad-Hotels-Palm-Spring-Inn.h18637272.Hotel-Information)

![A paved pathway flanked by palm trees and buildings with a clear sky above.](https://images.trvl-media.com/lodging/19000000/18640000/18637300/18637272/742f3ff7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: Erick R Gibbs Road 2, Oranjestad, BQ
- Location: 31.1 km from Windward Side
- Star rating: 3/5
- Guest rating: 8.2/10 (Very good, 16 reviews)
- Price: CA $204, CA $226 total, includes taxes & fees, Nov 19 - Nov 20
- Review: It not a place that have amenities to enjoy. For rest and go it is ok.

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.

[See all properties in Windward Side](https://www.expedia.ca/Hotel-Search?startDate=2026-11-26&endDate=2026-11-27&regionId=11638&adults=2&sort=RECOMMENDED&openPlayBack=true)

## Frequently Asked Questions

### How much does a Windward Side vacation package cost?

You'll find cheap prices on Expedia for your Windward Side escape. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Windward Side costs.

### What are the cheapest months to go to Windward Side?

April, June and July are the best times to search for cheap Windward Side vacation packages. Travelling in quieter months means you'll typically find reduced prices on flights and hotels.

### How many days is enough for Windward Side?

You can explore all the major sights in Windward Side within a few days, including the popular [Mt Scenery](https://www.expedia.ca/Mt-Scenery-Saba.d553248621533158272.Vacation-Attraction). If you want a longer Windward Side vacation, check out what sort of day trips and activities are available in the area.

### Is it worth booking a vacation package to Windward Side?

Whether you'd like to check out key attractions like [Dutch Museum of Saba](https://www.expedia.ca/Dutch-Museum-Of-Saba-Saba.d553248621584952178.Vacation-Attraction) and [Saba Heritage Centre](https://www.expedia.ca/Saba-Heritage-Center-Saba.d808648223374106624.Vacation-Attraction) on your Windward Side vacation, or coming for its great walking trails, nature and underwater activities, there's something for everyone here. With so much to see and do, you'll soon learn why so many people think Windward Side is a good vacation destination.

### How to find the best Windward Side package deals?

Use Expedia's filters to find some fabulous Windward Side package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Windward Side package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.

### Is it cheaper to book a Windward Side vacation as a package?

You can enjoy significant savings on your next Windward Side break by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.

### When to book a vacation package to Windward Side?

If you have your Windward Side travel dates locked in, book early to grab some unbeatable deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for jetting off on a whim.

### How to plan a trip to Windward Side?

1. Choose when to go: Check your calendar and get packing. Your preferred season and the activities available will also help you decide when to visit Windward Side.
2. Plan your budget wisely: As well as the price of your accommodations, you'll need to factor in other expenses. These include transportation, food and flights. Also, put aside a little extra for unexpected costs that may crop up during your trip to Windward Side.
3. Work out your trip length: Think about how long you'd like to spend exploring Windward Side. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to choose a Windward Side vacation package that brings all your bookings together.

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

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