Title: Book the Best BEACH RESORTS in Windward Side from CA $171 - Windward Side Hotels on the Beach| Expedia.ca

  

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Photo by Meghan Watters

# Find beach hotels in Windward Side from CA $171

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## Check availability on Windward Side Beach Hotel

Tonight

[Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=11638&startDate=2025-11-02&endDate=2025-11-03&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach)

Tomorrow

[Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=11638&startDate=2025-11-03&endDate=2025-11-04&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach)

Next weekend

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=11638&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach)

In two weeks

[Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=11638&startDate=2025-11-14&endDate=2025-11-16&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach)

## Top Windward Side Beach Hotel

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/12000000/11950000/11944600/11944556/33fcc0f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/12000000/11950000/11944600/11944556/32bbfd4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Cottage, 2 Single Beds, Private Bathroom, Ocean View](https://images.trvl-media.com/lodging/12000000/11950000/11944600/11944556/a8feb0e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/12000000/11950000/11944600/11944556/4dde38ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### El Momo Cottages

Windward Side

8.6/10

Excellent

(54)

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

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Georgina

CA $160

CA $171 total

includes taxes & fees

Nov 19 - Nov 20

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

![Outdoor dining](https://images.trvl-media.com/lodging/28000000/27140000/27131600/27131549/33d59b59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/28000000/27140000/27131600/27131549/75f810e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/28000000/27140000/27131600/27131549/c518168f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27140000/27131600/27131549/922e9d5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spyglass is a Private Villa With 360 View Near Windwardside.

windwardside

9.8/10

Exceptional

(69)

"Amazing views every day. Beautiful property with all the amenities you could want. The best property we have ever rented"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Charles S.

[](https://www.expedia.ca/Windward-Side-Hotels-Spyglass-Is-A-Private-Villa-With-360-View-Near-Windwardside.h27131549.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/79000000/78390000/78382900/78382857/a524e520.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78390000/78382900/78382857/f051d66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/79000000/78390000/78382900/78382857/f593f7a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78390000/78382900/78382857/ddacd38c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!

Windward Side

10/10

Exceptional

(11)

"Very pleased with the responsiveness of the owner, and location of the property. Exactly what we were looking for. Hope to stay again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alan F.

[](https://www.expedia.ca/Windward-Side-Hotels-Historic-Saban-Cottage-In-Windwardside.h78382857.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-16&endDate=2025-11-17&regionId=11638&adults=2&travelerType=beach&sort=RECOMMENDED&openPlayBack=true)

## Top Windward Side Hotel Reviews

![El Momo Cottages](//images.trvl-media.com/lodging/12000000/11950000/11944600/11944556/33fcc0f7_y.jpg)

### El Momo Cottages

10/10 Excellent

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

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

![The Old Gin House](//images.trvl-media.com/lodging/9000000/8280000/8273400/8273394/c4569144_y.jpg)

### The Old Gin House

10/10 Excellent

"hotel is close to town, at the ocean/beach, walkable and had good access to some nice options for lunch and diner, at hotel and nearby"

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

## Frequently asked questions

### What is Windward Side like for travelers who love the beach?

> Find a great place to stay in Windward Side, which has a lot to offer the traveler looking to book a beach vacation.

### When's the best time for a beach vacation in Windward Side?

> Plan your trip to the beach with a look at year-round temperatures in Windward Side: The hottest months are usually September and October with an average temp of 83°F, while the coldest months are February and March with an average of 78°F. Average annual precipitation for Windward Side is 36 inches.

### What is there to see and do around Windward Side?

> After arriving and checking into your hotel, you'll probably want to explore your surroundings. If you're eager to check out the beaches, head to Well's Bay Beach or Cove Bay Beach for some relaxation by the water. Make time for a range of local attractions, which include Saba Heritage Center and Dutch Museum of Saba. For additional things to see and do, consider a visit to Mt Scenery or Harry L Johnson Museum.

### What's the best way to get to my beach hotel in Windward Side?

> Here's some information to help you get to and around your beach accommodation in Windward Side with ease. The closest major airport is Saba (SAB-Juancho E. Yrausquin), located 1.3 mi (2.1 km) from the city center. If you'd like to venture out around the area, you may want a rental car for your journey.