Windy Hill Vacation Rentals from $68: Search Short-Term Rentals

Q: What's the top vacation rental that Windy Hill has to offer?

The Gem - by Zenbreak : You might like this vacation home rental near Windy Hill. It comes with free WiFi so you can feel at home during your trip.

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Our top choices for Windy Hill vacation rentals

A café interior with a display case of pastries, a refrigerated display, and a shelf with beverages.

1. The Palms Resort

Holetown

Dominique merida

$115 nightly

Oct 19 - Oct 20

Total with taxes and fees

A two-story building with a white and orange facade, a gated entrance, and a staircase leading to the upper floor.

2. Manderley Villas

Mangrove

STEPHIAN

$83 nightly

Nov 18 - Nov 19

Total with taxes and fees

A two-story house with a green exterior, a white gate, and a palm tree in the yard.

3. Malfranza Apartments

Bridgetown

Marc Downing

$78 nightly

Oct 19 - Oct 20

Total with taxes and fees

A clear blue pool surrounded by lounge chairs and palm trees, with a tiled edge and a metal ladder.

4. All Seasons Resort - Europa

Holetown

Tessa

$177 nightly

Oct 19 - Oct 20

Total with taxes and fees

A pool area with lounge chairs and a green umbrella.

5. Regent Apartments

Holetown

Yogui

$96 nightly

Nov 8 - Nov 9

Total with taxes and fees

A two-story building with a balcony, a door with a window, and a small porch.

6. Jem Gems

Durants

Laurence

$53 nightly

Nov 17 - Nov 18

Total with taxes and fees

A bedroom with a bed, a window with curtains, and a tiled floor.

7. The Terraces at Mangrove

Mangrove

Alison

$71 nightly

Oct 20 - Oct 21

Total with taxes and fees

A tropical beach setting with palm trees, a clear blue sky, and ocean waves.

8. Ocean Spray Apartments

Inch Marlowe

Lloyd

$75 nightly

Nov 17 - Nov 18

Total with taxes and fees

A wall with the text "Stay A While" in a stylized font.

9. Stay a While Guest Apartment

Mangrove

Karen

$81 nightly

Oct 19 - Oct 20

Total with taxes and fees

10. Blue Haven Holiday Apartments

St. Lawrence Gap

Raymond

$101 nightly

Oct 24 - Oct 25

Total with taxes and fees

A swimming pool with metal railings, a white fence, and buildings with balconies in the background.

11. Sunset Lane

Holetown

Ricardo

$118 nightly

Nov 1 - Nov 2

Total with taxes and fees

A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a building with balconies.

12. Plum Tree Club

Rockley

Saneka

$89 nightly

Nov 7 - Nov 8

Total with taxes and fees

An outdoor swimming pool with lounge chairs and a table, surrounded by a white wall and greenery.

13. THE Cottage, Saint Davids, Christ Church, Barbados

Oistins

Sean

$180 nightly

Oct 20 - Oct 21

Total with taxes and fees

A beach with clear turquoise water and a sandy shore.

14. BLR Villas Dover Beach

St. Lawrence Gap

Michelangelo

$53 nightly

Oct 24 - Oct 25

Total with taxes and fees

A palm tree with pink flowers, a clear blue sky, and a calm sea with a boat in the distance.

15. Breezy Vistas, Terrace – Saint James One‑Bedroom, Sea Breeze, WiFi & Parking

Westmoreland St James Barbados

Peter

$151 nightly

Nov 5 - Nov 6

Total with taxes and fees

A beach with clear turquoise water, a sailboat, and a forested area in the background.

16. Kingsgate #1 - by Zenbreak

Gibbes

John

$282 nightly

Oct 31 - Nov 1

Total with taxes and fees

A pool area with lounge chairs and umbrellas, a woman in a swimsuit, and a two-story building with balconies.

17. Sea Symphony Villa

Fryers Well

DOMINIQUE

$252 nightly

Oct 19 - Oct 20

Total with taxes and fees

A sandy beach with calm waters, trees, and a clear sky.

18. A Haven Away ~From~ Home

St. James

C E.

$150 nightly

Nov 12 - Nov 13

Total with taxes and fees

A beach with lounge chairs and umbrellas, a clear sky, and the ocean.

19. On the beautiful West Coast. Douglas, St. Peter, Barbados - Apt A

Heywoods Estates

Ann E.

$157 nightly

Oct 19 - Oct 20

Total with taxes and fees

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Top Windy Hill Hotel Reviews

Hilton Barbados Resort

8/10 Good

"The stay was good other than some complications with the shower to regulate the heat however the staff was very helpful in resolving the issue . I also noticed some mould in the bathroom. Other than that it was a great stay and wonderful location."

Turtle Beach, a Tribute Portfolio™ All Inclusive Hotel

10/10 Excellent

"This resort was smaller than the places I usually stay, but I absolutely loved it! ❤️ Although the food options were limited, everything was delicious every day. Breakfast was the same each morning, but I really appreciated that if there was something you didn’t eat or you wanted something different, the staff would happily prepare it for you. The staff was incredibly pleasant, friendly, and welcoming. A special shout-out to my girl Shanika! 🥰 She always made sure we had our drinks and that we were well taken care of throughout our stay. You definitely made our experience extra special! My kids really enjoyed the kids’ club and the ice cream shop, while my favorite spot was the coffee café, where I could grab my favorite frappe to cool down. ☕️🍦 The room was amazing! It was fully renovated, modern, and clean. My only disappointment was the beach right at the resort, as the water was rough and it wasn’t quite what I expected. However, there was a beautiful beach just about five minutes away, which made up for it! Overall, we had a wonderful stay, and I would definitely return to this resort. Sometimes, it’s not about how big or fancy a resort is, but the experience, the food, and the people who make your vacation memorable. I would absolutely recommend giving this place a try! 🌴☀️❤️"

Waves Resort & Spa, Barbados, An Autograph Collection® All-Inclusive Resort

10/10 Excellent

"This was our third visit to this hotel. We still love it ! The staff are fantastic the room we had ( a standard room) was huge compared to many, cleaned and refreshed every day . Even on the beach drinks, iced lollies and cold flannels are plentiful and regular. There could not be more choice at breakfast. Continental and English . However , and this really hurts me to say, generally dinner in the main restaurant was okay but Dosa the al a cart evening restaurant which we had no choice but to eat in is now Indian restaurant and serves hot or curried food was not . I hate curry and hot spice , spice and flavour fine heat is not . We had no choice but to pay to eat elsewhere. It used to be Fusion and that was nice I know that’s a personal dislike but there was no choice about it! Having said that we still love the place and would recommend it It really is excellent value for money We will return"

Bougainvillea Barbados

8/10 Good

"The property is very pretty with flowers and palms prolific. The rooms are adequate but ours on the ground floor was dark, with no real view other than the side of the pool. I would choose a 2nd or 3rd floor with more light and view. Product is the White Company, British. Nothing provided to wash your face , cloth or cotton pads. The staff are lovely and very accommodating. The cafe on site was closed for reno’s, ready in a week or so, however the hotel owns Deia, the property next door, a beach club with a good casual restaurant on the beach with easy access."

Hotel Indigo Bridgetown Barbados by IHG

8/10 Good

"Guys this was a great hotel and i enjoyed my brief stay. Food was excellent - try the bajan roll on the roof top with a nice cocktail. my only little flaw which i mentioned upon checkout was that the pool music was left on loudly all night and i could hear it from my room."

Find out more about Windy Hill

Everything you need to know about Windy Hill vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windy Hill vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windy Hill vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windy Hill vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windy Hill. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windy Hill in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $68 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windy Hill rentals

At Expedia, we put the best Windy Hill vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windy Hill rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windy Hill vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windy Hill. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Can I find a vacation rental in Windy Hill?

Yes, we give you a choice of vacation rentals near the most popular local attractions in Windy Hill, or you can choose a more secluded option if you want a relaxing place to stay. Nature enthusiasts will enjoy the beaches in Windy Hill. Make sure you have time to check out the restaurants while you're in the area.

What's the top vacation rental that Windy Hill has to offer?

The Gem - by Zenbreak: You might like this vacation home rental near Windy Hill. It comes with free WiFi so you can feel at home during your trip.

What’s there to see and do in Windy Hill?

Explore the area and family-friendly sights such as Oistin's Friday Night Fish Fry, or get out into nature at a spot like Bathsheba Beach. In the larger area, you’ll find Harrison's Cave and Royal Westmoreland Golf Course.

What’s a vacation rental in Windy Hill like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Windy Hill. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a family trip.

Windy Hill Vacation Rentals

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Check prices for these dates

Our top choices for Windy Hill vacation rentals

1. The Palms Resort

2. Manderley Villas

3. Malfranza Apartments

4. All Seasons Resort - Europa

5. Regent Apartments

6. Jem Gems

7. The Terraces at Mangrove

8. Ocean Spray Apartments

9. Stay a While Guest Apartment

10. Blue Haven Holiday Apartments

11. Sunset Lane

12. Plum Tree Club

13. THE Cottage, Saint Davids, Christ Church, Barbados

14. BLR Villas Dover Beach

15. Breezy Vistas, Terrace – Saint James One‑Bedroom, Sea Breeze, WiFi & Parking

16. Kingsgate #1 - by Zenbreak

17. Sea Symphony Villa

18. A Haven Away ~From~ Home

19. On the beautiful West Coast. Douglas, St. Peter, Barbados - Apt A

Find vacation rentals that suit your style

Top Windy Hill Hotel Reviews

Hilton Barbados Resort

Find out more about Windy Hill

Explore a world of travel with Expedia

Frequently asked questions

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