A coastal town with buildings and a large wave crashing onto the shore.

Hillsborough Vacation Rentals

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Our top choices for Hillsborough vacation rentals

Bogles Round House

Bogles Round House
2.5 star property
Hillsborough
8.8 out of 10, Excellent, (72 reviews)
"I stay at the Round House whenever I visit Carriacou. I was happy to hear that the Hotel was not too badly damaged after the 2024 hurricane and as usual, had a very enjoyable stay."
United States
Jonathan
The price is CA $154
CA $169 total
includes taxes & fees
Aug 22 - Aug 23
Bogles Round House

Luxurious one bedroom cottage

Luxurious one bedroom cottage
Carriacou and Petite Martinique
9.8 out of 10, Exceptional, (12 reviews)
"Clean rooms, comfortable bed. Excellent host and enchanting property."
United States
Chadwick
The price is CA $182
CA $210 total
includes taxes & fees
Aug 3 - Aug 4
Luxurious one bedroom cottage

luxurious two bedroom apartment

luxurious two bedroom apartment
Carriacou and Petite Martinique
10.0 out of 10, Exceptional, (16 reviews)
"Beautiful views, extremely helpful and attentive staff. Best place to stay on Carriacou."
United States
Kenneth
The price is CA $266
CA $300 total
includes taxes & fees
Jul 26 - Jul 27
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

Find out more about Hillsborough

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Hillsborough. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Hillsborough?

Yes, we offer vacation rentals near top sights in Hillsborough, or you can go with a more secluded option if you want a relaxing place to 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 vacation rentals that Hillsborough has to offer?

Paradise Beach House: This highly rated vacation home rental in Hillsborough is located near the beach and has a terrace, a garden, and a barbecue grill to put you at ease in your new surroundings. Our travelers also rate Voted best beach house in 2026 by us as a favorite home for rent in Hillsborough.

How many vacation rentals are there in Hillsborough?

With 6 Expedia vacation rentals, you're sure 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 larger area, you’ll find Tyrell Bay Beach and Tobago Cays.

What’s a vacation rental in Hillsborough like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in Hillsborough. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for families.