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, (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 ¥15,477
¥17,025 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Bogles Round House

BLACK FRIDAY DEAL 50% OFF April 1 to June 30 minimum 7 day stay

BLACK FRIDAY DEAL 50% OFF April 1 to June 30 minimum 7 day stay
L’Esterre
10.0 out of 10, Exceptional, (14)
"Excellent location. Very communicative, lots of great dine gems close by. People are amazing in Carriacou!"
Canada
Laura O.
BLACK FRIDAY DEAL 50% OFF April 1 to June 30 minimum 7 day stay

Caribbean house 3 mins walk to the marina and port.

Caribbean house 3 mins walk to the marina and port.
Carriacou and Petite Martinique
Caribbean house 3 mins walk to the marina and port.

Comfortable apartment close to Tyrell Bay Marina

Comfortable apartment close to Tyrell Bay Marina
Argyle
Comfortable apartment close to Tyrell Bay Marina

Beach villa with 3 bedrooms, 3 bathrooms and private pool in Carriacou, Grenada

Beach villa with 3 bedrooms, 3 bathrooms and private pool in Carriacou, Grenada
L'Esterre
10.0 out of 10, Exceptional, (2)
"beautiful villa, beautiful island, beautiful people. "
United Kingdom
David B.
Beach villa with 3 bedrooms, 3 bathrooms and private pool in Carriacou, Grenada

Longue-Vue Villa, Carriacou, Grenadines Pool -Spectacular Sunsets -Two Bedrooms

Longue-Vue Villa, Carriacou, Grenadines Pool -Spectacular Sunsets -Two Bedrooms
Craigston
Longue-Vue Villa, Carriacou, Grenadines Pool -Spectacular Sunsets -Two Bedrooms

Spacious 2-bed House in Carriacou

Spacious 2-bed House in Carriacou
2.0 star property
Hillsborough
Spacious 2-bed House in Carriacou

2 Bedroom with Incredible Sea View

2 Bedroom with Incredible Sea View
Carriacou and Petite Martinique
2 Bedroom with Incredible Sea View

Scraper's Guest House

Scraper's Guest House
3.0 star property
Hillsborough
Scraper's Guest House

Paradise Beach House

Paradise Beach House
3.0 star property
Hillsborough
Paradise Beach House

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 ¥29,252
¥32,966 total
includes taxes & fees
Dec 31 - Jan 1, 2026
luxurious two bedroom apartment

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.
The price is ¥19,965
¥23,060 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Luxurious one bedroom cottage

Comfortable Apartment close to Tyrell Bay Marina

Comfortable Apartment close to Tyrell Bay Marina
Carriacou
Comfortable Apartment close to Tyrell Bay Marina

Bahari....

Bahari....
Windward
Bahari....
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

Search for holiday rentals in Hillsborough on Expedia! You can easily find your home rentals, villas, holiday apartments in Hillsborough using one of the methods below:

  • View our selection of featured holiday rentals in Hillsborough
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  • Enter your travel dates to view the best deals on holiday rentals in Hillsborough while they last

Look no further and take a look at our great range of rental properties in Hillsborough!

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 Chatham 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.