Find the best cottages in Windward Side - We found 5 exact matches
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About Windward Side Cottage Rentals on Vacation Cottage
For travelers seeking a comfortable and luxurious retreat in Windward Side, Vacation Cottage has you covered. Opt for a cottage rental, lake house retreat, or summer home resort and enjoy the flexibility of a hotel. With over 5 options available in Windward Side on Vacation Cottage, we can assist you in finding the perfect accommodation.
Elevate your next vacation with a picturesque cottage rental in Windward Side, offering top-notch amenities such as swimming pools, fitness centers, Wi-Fi, luxury suites, and fully-equipped kitchens. Discover unbeatable deals on outdoor vacation cottages, lake houses, and summer home retreats. Start planning your trip to Windward Side today and secure your accommodation in minutes on our website.
Whether it's a short-term getaway or a long-term seasonal stay, find the perfect cottage rental, lake house, or summer home for your favorite travel destinations. Compare options with Vacation Cottage and stay close to nature.
Frequently Asked Questions About Windward Side Rental Cottages
What are the top rated Cottage Rentals in Windward Side?
There are a lot of options in Windward Side. If you plan on staying in the Windward Side area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Windward Side:
- Saba Arawak Hotel
- El Momo Cottages
- Saba Arawak Hotel
- Queen’s hotel, bar & kitchen
- Haiku House, an amazing wooden villa situated in a tropical forest
- Caribbean Elegance & Comfort
- Modern Luxury Villa in Flatlands. Pool. Walk to Beach. Sleeps 6. Ocean Views.
- Home a way from home in the Unspoiled queen of the Caribbean.
- 2023 Villa Fairview on Saba. Ultimate privacy.
- Spyglass is a Private Villa With 360 View Near Windwardside.
How much does it cost to rent a cottage in Windward Side?
The average cost for a cottage rental in Windward Side is $167 per night. Vacation Cottage has a wide list of great cottages near Windward Side that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Windward Side that allow pets?
Yes, here are the top cottage rentals in Windward Side that allow you to bring your pet:
- Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
- El Momo Cottages
- Beautiful Gingerbread Cottage - Spectacular View & Pool
- Your very own cottage
- Haiku House, an amazing wooden villa situated in a tropical forest
- Saba Arawak Hotel
- El Momo Cottages
- Caribbean Elegance & Comfort
See all pet-friendly vacation rentals in Windward Side on Vacation Cottage
Do you have any rental cottages in Windward Side that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Windward Side to find one that works for you.
Are there quality cottages in Windward Side that have indoor swimming pools?
As of 2026, the data from Vacation Cottage shows that there are Over 5 private swimming pools or cottages with indoor pools in the Windward Side area along with other great amenities.
Do any cottages in Windward Side have hot tubs?
About 5 cottages in Windward Side boast of premium hot tubs. Some of the popular places to stay with hot tubs include:
See all holiday vacation rentals in Windward Side on Vacation CottageAre there luxury cottages in Windward Side?
Yes, there are luxury cottages in Windward Side. Find more luxury, lakefront, winter, & last-minute cottage rentals near Windward Side.
