Hillsborough Holiday Rentals

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Tonight
18 Nov - 19 Nov
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19 Nov - 20 Nov
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21 Nov - 23 Nov
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28 Nov - 30 Nov

Holiday Rentals in Hillsborough

On the beach
Bogles Round House

Bogles Round House

2.5 star property
Hillsborough
8.8 out of 10, Excellent, (62)
"Superb accommodation! The cottage was spotless and had everything we needed. The bed was adequate, and the air conditioning worked perfectly. The kitchen was well equipped and easy to use. We had the upstairs apartment with two double rooms, which was ideal for myself and my daughter. The views were absolutely stunning, and the on-site restaurant was fantastic — delicious food and excellent service. Roxanne and her team did a brilliant job and made us feel so welcome. This was my second stay...
United Kingdom
Monica
The price is NZ$195
includes taxes & fees
21 Nov - 22 Nov
Bogles Round House
Marina
Luxurious one bedroom cottage

Luxurious one bedroom cottage

Carriacou and Petite Martinique
9.6 out of 10, Exceptional, (8)
"Our stay at this location was extremely comfortable. Everything met our expectations."
Canada
Penelope J.
The price is NZ$262
includes taxes & fees
4 Dec - 5 Dec
Luxurious one bedroom cottage
Marina
luxurious two bedroom apartment

luxurious two bedroom apartment

Carriacou and Petite Martinique
10.0 out of 10, Exceptional, (12)
"Our stay at Dees Pearl was like being home with family. The accommodation was very comfortable and had everything we needed for our stay. Dave and family made us feel at home and provided us with anything we needed including rides to and from any location we desired. We definitely plan to return again soon."
Canada
Lanita R. L.
The price is NZ$382
includes taxes & fees
19 Nov - 20 Nov
luxurious two bedroom apartment
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.
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Top Hillsborough Hotel Reviews

Bogles Round House

Bogles Round House

10/10 Excellent
"Superb accommodation! The cottage was spotless and had everything we needed. The bed was adequate, and the air conditioning worked perfectly. The kitchen was well equipped and easy to use. We had the upstairs apartment with two double rooms, which was ideal for myself and my daughter. The views were absolutely stunning, and the on-site restaurant was fantastic — delicious food and excellent service. Roxanne and her team did a brilliant job and made us feel so welcome. This was my second stay at Bogles Roundhouse Cottages, and it certainly won’t be my last. Highly recommend this place to anyone visiting Carriacou!"
Monica 10-night trip
Posted 9 days ago
Bogles Round House
Green Roof Inn

Green Roof Inn

2/10 Terrible
"The Inn stole my money. I arrived on February 24th and did not like the property. There was no internet. There was no air conditioning and the manager said. I did not have to pay period they charge my credit card and I tried to stop the payment. The manager lied to me and said that they called the owner or Expedia. And cancel the reservation they did not. I ended up having to pay for $282 for 2 nights. And did not even stay at the property. I paid to stay somewhere else. So I paid twice as suggest not staying at this property. There was nobody there. It was like a ghost town and another couple had showed app around the same time. I did and they decided not to stay there either. The place was a long walk from the center of town. I have been ripped off and don't like it."
Steven 2-night trip
Posted 9 months ago
Green Roof Inn

Find out more about Hillsborough

Everything you need to know about Hillsborough holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Hillsborough holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 Hillsborough holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Hillsborough holiday rentals: An excellent choice for every season

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hillsborough holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hillsborough holiday rentals we have selected for you start as low as NZ$195 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Hillsborough rentals

At Expedia, we put the best Hillsborough holiday 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 Hillsborough 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 Hillsborough holiday.

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

Frequently asked questions

Are there holiday rentals in Hillsborough?

Yes, there are holiday rentals close to the most popular sights in Hillsborough, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Hillsborough. Make sure you have time to check out the gardens while you're in the area.

What are some of the best holiday rentals that Hillsborough has to offer?

Paradise Beach House: This highly rated holiday home rental in Hillsborough is located near the beach, and has a terrace, a garden and a BBQ to put you at ease in your new surroundings. Another good choice for your trip to Hillsborough is BOOK NOW January 2026 dates have just become available.

How many holiday rentals are there in Hillsborough?

With 5 Expedia holiday rentals, you're guaranteed to find just the right place for your Hillsborough stay.

What’s there to see and do in Hillsborough?

Cultural attractions include Carriacou Museum, whereas Sandy Island is a spot to enjoy nature. In the wider area, you’ll find Tyrell Bay Beach and Tobago Cays.

What’s a holiday rental in Hillsborough like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Hillsborough. Holiday rentals feature amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a family trip or a small group gathering.