Hillsborough Vacation Rentals

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Vacation Rentals in Hillsborough

On the beach
Bogles Round House
Bogles Round House
2.5 star property
8.8 out of 10, Excellent, (61)
"This is a beautiful location right beside a black sand beach. "
Canada
Michelle
$100 nightly
The price is $110
Oct 26 - Oct 27
Total with taxes and fees
Bogles Round House
Fridge, microwave, oven, stovetop
Caribbean house 3 mins walk to the marina and port.
Caribbean house 3 mins walk to the marina and port.
Caribbean house 3 mins walk to the marina and port.
Terrace/patio
BOOK NOW January 2026 dates have just become available
BOOK NOW January 2026 dates have just become available
10.0 out of 10, Exceptional, (14)
"We very much enjoyed the beach house. It was everything we wanted and more ! Great house, great beach, great people . Easy to communicate with everyone and we loved the culture and the locals as well as delicious rotis and abundance of fish ."
Canada
Janice W.
BOOK NOW January 2026 dates have just become available
Outdoor pool
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
10.0 out of 10, Exceptional, (2)
"Beautiful home situated in the best location on Carriacou! Expertly designed! Creatively decorated! Very relaxing and guiet! Great local restaurants with a strong island vibe! We thoroughly enjoyed our stay at Las Tortugas!"
United States
Clark C.
Beach villa with 3 bedrooms, 3 bathrooms and private pool in Carriacou, Grenada
Beach
Longue-Vue Villa, Carriacou, Grenadines Pool -Spectacular Sunsets -Two Bedrooms
Longue-Vue Villa, Carriacou, Grenadines Pool -Spectacular Sunsets -Two Bedrooms
Longue-Vue Villa, Carriacou, Grenadines Pool -Spectacular Sunsets -Two Bedrooms
Beach
2 Bedroom with Incredible Sea View
2 Bedroom with Incredible Sea View
2 Bedroom with Incredible Sea View
House | Interior
Spacious 2-bed House in Carriacou
Spacious 2-bed House in Carriacou
2.0 star property
Spacious 2-bed House in Carriacou
BBQ/picnic area
Paradise Beach House
Paradise Beach House
3.0 star property
Paradise Beach House
Beach
Scraper's Guest House
Scraper's Guest House
3.0 star property
Scraper's Guest House
Outdoor dining
The Boat House Studio Tyrell Bay
The Boat House Studio Tyrell Bay
10.0 out of 10, Exceptional, (1)
"I had a wonderful stay at this property and will definitely stay there again on my next trip to Carriacou.....hopefully soon. The accomodation is as advertised and the landlord is very helpful and considerate of his guests. Thank you."
United States
Rosetta W.
The Boat House Studio Tyrell Bay
Marina
Luxurious one bedroom cottage
Luxurious one bedroom cottage
9.6 out of 10, Exceptional, (8)
"An absolute Jem in Carriacou! Will definitely be staying there again anytime I am in there area. Thank you to Dave and Ayeesha for a fabulous stay, fantastic hospitality and overall experience."
United States
Brooke
$149 nightly
The price is $149
Oct 26 - Oct 27
Total with taxes and fees
Luxurious one bedroom cottage
Marina
luxurious two bedroom apartment
luxurious two bedroom apartment
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
Oct 24 - Oct 25
Total with taxes and fees
luxurious two bedroom apartment
Fridge, microwave, oven, stovetop
Comfortable Apartment close to Tyrell Bay Marina
Comfortable Apartment close to Tyrell Bay Marina
Comfortable Apartment close to Tyrell Bay Marina
Marina
The Boat House Tyrrel Bay
The Boat House Tyrrel Bay
The Boat House Tyrrel Bay
Property grounds
Bahari....
Bahari....
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

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 8 months ago
Green Roof Inn
Bogles Round House

Bogles Round House

10/10 Excellent
"We absolutely loved everything about this place and Roxanne, Ingy and Naka were the best hosts we have experienced on our many travels. Beautiful natural surroundings and views. Roxanne restaurant (the old slip way) is well worth a visit - superb food and ambiance. Also paradise beach. "
Zoë 3-night trip
Posted 1 year 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 BOOK NOW January 2026 dates have just become available.

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 Chatham Bay Beach.

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.