Hillsborough Vacation Rentals

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Jan 9 - Jan 11

Our top choices for Hillsborough vacation rentals

On the beach
Bogles Round House

Bogles Round House

Bogles Round House
2.5 star property
Hillsborough
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
$100 nightly
The price is $110
Jan 16 - Jan 17
Total with taxes and fees
Bogles Round House
Marina
Luxurious one bedroom cottage

Luxurious one bedroom cottage

Luxurious one bedroom cottage
Carriacou and Petite Martinique
9.6 out of 10, Exceptional, (9)
"Our stay at this location was extremely comfortable. Everything met our expectations."
Canada
Penelope J.
$149 nightly
The price is $149
Jan 8 - Jan 9
Total with taxes and fees
Luxurious one bedroom cottage
Marina
luxurious two bedroom apartment

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.
$215 nightly
The price is $215
Jan 11 - Jan 12
Total with taxes and fees
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
"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 3 weeks ago
Bogles Round House

Find out more about Hillsborough

Everything you need to know about Hillsborough 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 Hillsborough 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 Hillsborough vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Hillsborough vacation 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 low season months. For more hustle and bustle, you may prefer to visit Hillsborough 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 $110 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 Hillsborough rentals

At Expedia, we put the best Hillsborough 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 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 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 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.

Explore a world of travel with Expedia

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. Another good choice for your trip to Hillsborough is BLACK FRIDAY DEAL 50% OFF April 1 to June 30 minimum 7 day stay.

How many vacation rentals are there in Hillsborough?

With 5 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.