New
Cottage
2 Bedrooms
4 Guests
Private Pool
Pool
Ocean View
Balcony/Terrace
AU $573/Night
7 Nights - AU $4,013
Windward Side Cottage Rentals & Holiday Homes
Find the best cottages in Windward Side - We found 6 exact matches
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Compare Cottage Rentals in Windward Side
AU $181/Night
7 Nights - AU $1,270
Cottage
5.0(2 Reviews)
2 Bedrooms
6 Guests
- Balcony/Terrace
Kitchen
Air Conditioner
Internet
AU $272/Night
7 Nights - AU $1,906
Cottage
4.8(27 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
AU $302/Night
7 Nights - AU $2,117
Cottage
1 Bedroom
2 Guests
- Air Conditioner
Child Friendly
Laundry
Bedding/Linens
AU $238/Night
7 Nights - AU $1,664
Cottage
1 Bedroom
2 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
Pet Friendly
AU $210/Night
7 Nights - AU $1,472
People Visiting Windward Side Also Like
Villa
10.0(7 Reviews)
3 Bedrooms
6 Guests
- Private Pool
Breakfast
Parking- Pool
AU $1,456/Night
7 Nights - AU $10,192
AU $206/Night
7 Nights - AU $1,442
AU $137/Night
7 Nights - AU $958
Villa
10.0(4 Reviews)
2 Bedrooms
6 Guests
- Private Pool
Oceanfront- Parking
- Pool
AU $1,109/Night
7 Nights - AU $7,763
AU $599/Night
7 Nights - AU $4,193
AU $368/Night
7 Nights - AU $2,575
House
10.0(4 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
AU $488/Night
7 Nights - AU $3,415
Bed & Breakfast
4.7(72 Reviews)
1 Bedroom
- Balcony/Terrace
- Child Friendly
- Laundry
AU $151/Night
7 Nights - AU $1,056
Villa
5.0(2 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
AU $616/Night
7 Nights - AU $4,315
AU $186/Night
7 Nights - AU $1,301
House
5.0(2 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Pool
- Kitchen
- Air Conditioner
AU $356/Night
7 Nights - AU $2,490
AU $1,458/Night
7 Nights - AU $10,207
Villa
5.0(1 Review)
3 Bedrooms
6 Guests
- Pet Friendly
- Child Friendly
AU $638/Night
7 Nights - AU $4,468
Villa
4.9(59 Reviews)
3 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
AU $578/Night
7 Nights - AU $4,043
Villa
4.9(9 Reviews)
5 Bedrooms
12 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
AU $547/Night
7 Nights - AU $3,831
House
4.7(3 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Pool
- Kitchen
- Bedding/Linens
AU $540/Night
7 Nights - AU $3,781
AU $987/Night
7 Nights - AU $6,906
AU $519/Night
7 Nights - AU $3,630
About Windward Side Cottage Rentals on BedroomVillas.com.au
Seeking incredible premium cottages to rent near Windward Side? BedroomVillas features more than 6 cottages that are ideal for your next trip. Discover high-end cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Windward Side have hot baths, are kid-friendly & family-friendly, and are near top local attractions, to give guests the best travel experience they could ever wish for. BedroomVillas’ cottage listings come in all shapes and sizes for large groups, friends, or couples in Windward Side.
Are you planning to travel to a lakeside, beach, or mountain area? Then we've got the places for you. BedroomVilla’s cottage rentals and boutique resorts and rentals offer a great selection, giving you direct access to the owners of these cottage properties, and providing you the best opportunity to find a great price for a great stay.
BedroomVillas offers 6 luxury holiday cottages and places to stay in Windward Side. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget. Relax with BedroomVillas.
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
- Scenery Hotel Saba
- Haiku House, an amazing wooden villa situated in a tropical forest
- Modern Luxury Private Villa w Pool and Ocean Views. Walk to Beach. Sleeps 6.
- Beautiful Traditional Saba Cottage With all the Modern Amenities
- El Momo Cottages
- Saba Arawak Hotel
- Queen’s hotel, bar & kitchen
- Caribbean Elegance & Comfort
- Home a way from home in the Unspoiled queen of the Caribbean.
How much does it cost to rent a cottage in Windward Side?
The average cost for a cottage rental in Windward Side is $206 per night. BedroomVillas.com.au 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:
- Compass Cottage: Breathtaking Views on Saba, the Caribbean’s “Unspoiled Queen”
- El Momo Cottages
- Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
- Beautiful Gingerbread Cottage - Spectacular View & Pool
- Haiku House, an amazing wooden villa situated in a tropical forest
- Saba Arawak Hotel
- El Momo Cottages
- Modern Luxury Private Villa w Pool and Ocean Views. Walk to Beach. Sleeps 6.
See all pet-friendly vacation rentals in Windward Side on BedroomVillas.com.au
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 BedroomVillas.com.au shows that there are Over 6 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 6 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 BedroomVillas.com.au
Are 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.
