Hillsborough Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Hillsborough holiday rentals

On the beach
Bogles Round House

Cottage in Hillsborough

Bogles Round House
2.5 star property
8.8 out of 10, Excellent, (63)
"Such a peaceful experience listening to the waves all day/night and the views of the ocean and other islands are spectacular. Thank you to Roxanne and Miguel for making this trip so memorable! (Tip: ask Miguel to scoot you over to Anse La Roche for an unforgettable day/meal). Roxanne’s cooking at the restaurant was the best I’ve had in years. Delicious and gorgeously presented. Excellent stay! Will be back! "
United States
Juliet
The price is S$141
includes taxes & fees
29 Dec - 30 Dec
Bogles Round House
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
"Such a peaceful experience listening to the waves all day/night and the views of the ocean and other islands are spectacular. Thank you to Roxanne and Miguel for making this trip so memorable! (Tip: ask Miguel to scoot you over to Anse La Roche for an unforgettable day/meal). Roxanne’s cooking at the restaurant was the best I’ve had in years. Delicious and gorgeously presented. Excellent stay! Will be back! "
Juliet 6-night trip
Posted 13 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 10 months ago
Green Roof Inn

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.

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 Chatham 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.