Hillsborough Vacation Rentals from ￥17,025: Search Short-Term Rentals

Q: 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 .

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Our top choices for Hillsborough vacation rentals

Bogles Round House

Hillsborough

"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

￥17,025 total

includes taxes & fees

Dec 31 - Jan 1, 2026

Beach nearby, sun loungers, beach towels

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

L’Esterre

Laura O.

Caribbean house 3 mins walk to the marina and port.

Carriacou and Petite Martinique

Cookware/dishes/utensils, spices, lobster pot

Comfortable apartment close to Tyrell Bay Marina

Argyle

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

L'Esterre

David B.

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

Craigston

Spacious 2-bed House in Carriacou

Hillsborough

2 Bedroom with Incredible Sea View

Carriacou and Petite Martinique

Scraper's Guest House

Hillsborough

Paradise Beach House

Hillsborough

luxurious two bedroom apartment

Carriacou and Petite Martinique

Lanita R. L.

￥32,966 total

includes taxes & fees

Dec 31 - Jan 1, 2026

Luxurious one bedroom cottage

Carriacou and Petite Martinique

Penelope J.

￥23,060 total

includes taxes & fees

Jan 11 - Jan 12, 2026

Comfortable Apartment close to Tyrell Bay Marina

Carriacou

Bahari....

Windward

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Top Hillsborough Hotel Reviews

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! "

Luxurious one bedroom cottage

10/10 Excellent

"Dave, Ayeesha, and Davidson were all wonderful. My wife and I absolutely love this cottage, and hope to visit again soon! The land the cottage is on alone, gives you an incredible experience with all the different vegetation and animals. Transportation to and from Lauriston Airport were included with our package. Many wonderful restaurants close by. Grocery close by as well. Though the island is small, more than 7 days of amazing adventures await you. We highly recommend this property if you are looking for peace, quiet, sheer friendliness (from both the host family and all locals) and the most beautiful scenery!!"

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."

Find out more about Hillsborough

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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.

Hillsborough Vacation Rentals

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Check prices for these dates

Our top choices for Hillsborough vacation rentals

Bogles Round House

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

Caribbean house 3 mins walk to the marina and port.

Comfortable apartment close to Tyrell Bay Marina

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

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

Spacious 2-bed House in Carriacou

2 Bedroom with Incredible Sea View

Scraper's Guest House

Paradise Beach House

luxurious two bedroom apartment

Luxurious one bedroom cottage

Comfortable Apartment close to Tyrell Bay Marina

Bahari....

Top Hillsborough Hotel Reviews

Bogles Round House

Luxurious one bedroom cottage

Green Roof Inn

Find out more about Hillsborough

Frequently asked questions

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