Hillsborough Holiday Rentals

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Holiday Rentals in Hillsborough

Property grounds
Tranquil 2 bed Penthouse with sea views and 4 person Private Hot Tub, no traffic
10.0 out of 10, Exceptional, (2)
"Moira was a good communicator through WhatsApp. The sunsets were stunning and you could see the sail boats at Sandy Island. Mid day gets hot with no AC so we went to the beach and did exploring in the afternoons. Sleeping was comfortable enough under the ceiling fan."
Tranquil 2 bed Penthouse with sea views and 4 person Private Hot Tub, no traffic
Outdoor pool
Beach villa with 3 bedrooms, 3 bathrooms and private pool in Carriacou, Grenada
10.0 out of 10, Exceptional, (1)
"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!"
Beach villa with 3 bedrooms, 3 bathrooms and private pool in Carriacou, Grenada
Property grounds
Spring Deals- Book 7 nights in May or June get 1 night FREE
10.0 out of 10, Exceptional, (13)
"This place is unique. It’s the only thing like it on the best beach in Carriacou. Local folks are welcoming and it’s easy to walk or bus to anything you want, but there’s also little reason to go far except to explore. It was perfect for us."
Spring Deals- Book 7 nights in May or June get 1 night FREE
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Aerial view
One of the best locations on the island!!
10.0 out of 10, Exceptional, (15)
"We were lucky enough to spend 3 days in this peaceful paradise. The apartment is situated on the hills overlooking Tyrell Bay and is in walking distance to several restaurants. It was lovely to watch sailing boats enter the bay while we drank our morning coffee. Peaceful and quiet. It is located on a steep road, but we walked it several times, even though our host Dave or Alyessa would have picked us up, and there were taxis as well. The apartment is clean and decorated as a boat cabin, and the...
The price is NZ$227
includes taxes & fees
23 May - 24 May
One of the best locations on the island!!
Beach
luxurious two bedroom apartment
10.0 out of 10, Exceptional, (11)
"My family and I had a delightful stay in Carriacou in early May 2024. Dave, the host, called me a few days before our arrival and provided details regarding our stay, as well as things to do. He picked us up at the port, stopped at a local grocery store so we could pick up some provisions, and then took us to the apartment where we spent 2 nights and three days. Since the apartment sits up on the hillside, the views were spectacular! We had the Caribbean Sea on one side and the Atlantic Ocean on...
The price is NZ$351
includes taxes & fees
23 May - 24 May
luxurious two bedroom apartment
Property grounds
Secluded romantic getaway with the turquoise Caribbean sea just steps away.
10.0 out of 10, Exceptional, (3)
"If there was a 6 star option I would give 6 stars. Our stay was perfect. The location was great and secluded and Sue was an amazing host. She answered all our questions suggested things to do and places to eat. She communicated very well and made us feel so comfortable. Couldn’t have asked for a better weekend get away. We are already planning our trip back!"
Secluded romantic getaway with the turquoise Caribbean sea just steps away.
Aerial view
Luxurious one bedroom cottage
9.6 out of 10, Exceptional, (7)
"Our stay at this location was extremely comfortable. Everything met our expectations."
The price is NZ$251
includes taxes & fees
23 May - 24 May
Luxurious one bedroom cottage
Property grounds
Tranquil 2 Bed Apt, sea view, 2 Person Hot Tub, no traffic
9.0 out of 10, Wonderful, (4)
"Amazing stay!!! Beautiful views and loved waking up in the morning to the sounds of nature. The owners were very friendly and communicative. They attended to our concerns in an expeditious manner. I will definitely recommend and rent again."
Tranquil 2 Bed Apt, sea view, 2 Person Hot Tub, no traffic
On the beach
Bogles Round House
2.5 star property
8.8 out of 10, Excellent, (55)
"Nice cottage just a short walk from a small beach with occasional local visitors. The walk into Hillsborough is easy and a colorful immersion into the local scene. The breakfasts and dinners at the roundhouse are exceptional! Great place if you’re looking for a slower paced vacation!"
The price is NZ$163
includes taxes & fees
24 May - 25 May
Bogles Round House
Standard Room, 1 Double Bed | Terrace/patio
Cherryhill Apartment
3.0 star property
8.0 out of 10, Very good, (4)
"The cleanest guesthouse I have ever stayed in. Only stayed one night, but hosts were very welcome and even provided me a complimentary breakfast in the morning. Beautiful breeze and quiet at night, really nice stay."
Cherryhill Apartment
Beach
Longue-Vue Villa, Carriacou, Grenadines Pool -Spectacular Sunsets -Two Bedrooms
Longue-Vue Villa, Carriacou, Grenadines Pool -Spectacular Sunsets -Two Bedrooms
Cookware/dishes/utensils, spices, lobster pot
Comfortable apartment close to Tyrell Bay Marina
Comfortable apartment close to Tyrell Bay Marina
2 bedrooms, desk, iron/ironing board, free WiFi
2 bedroom cottage with incredible Sea View
2 bedroom cottage with incredible Sea View
BBQ/picnic area
Paradise Beach House
3.0 star property
Paradise Beach House
3 bedrooms, iron/ironing board, WiFi, bed sheets
Caribbean house 3 mins walk to the marina and port.
Caribbean house 3 mins walk to the marina and port.
House | Living area
Spacious 2-bed House in Carriacou
2.0 star property
Spacious 2-bed House in Carriacou
Beach
Scraper's Guest House
3.0 star property
Scraper's Guest House
Property grounds
The Boat House Studio Tyrell Bay
The Boat House Studio Tyrell Bay
Oven, stovetop, cookware/dishes/utensils, spices
The Boat House Tyrrel Bay
The Boat House Tyrrel Bay
1 bedroom, iron/ironing board, WiFi, bed sheets
Comfortable Apartment close to Tyrell Bay Marina
Comfortable Apartment close to Tyrell Bay Marina
Don't see what you're looking for?
See all available properties in Hillsborough
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.

Other types of properties in Hillsborough you may be interested in

Property grounds
Tranquil 2 bed Penthouse with sea views and 4 person Private Hot Tub, no traffic
10.0 out of 10, Exceptional, (2)
"Moira was a good communicator through WhatsApp. The sunsets were stunning and you could see the sail boats at Sandy Island. Mid day gets hot with no AC so we went to the beach and did exploring in the afternoons. Sleeping was comfortable enough under the ceiling fan."
Tranquil 2 bed Penthouse with sea views and 4 person Private Hot Tub, no traffic
Beach nearby, white sand
Rosa Guesthouse
3.0 star property
9.4 out of 10, Exceptional, (18)
"Gary and Beverly were great hosts. Very friendly people who also sell the best rotis in town on Friday and Saturday lunchtimes only. They were most accommodating to our needs. "
Rosa Guesthouse
On the beach
Bogles Round House
2.5 star property
8.8 out of 10, Excellent, (55)
"Nice cottage just a short walk from a small beach with occasional local visitors. The walk into Hillsborough is easy and a colorful immersion into the local scene. The breakfasts and dinners at the roundhouse are exceptional! Great place if you’re looking for a slower paced vacation!"
The price is NZ$163
includes taxes & fees
24 May - 25 May
Bogles Round House
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Hillsborough holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Hillsborough. 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 Hillsborough. 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 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 holiday 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 Hillsborough short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Hillsborough?

Yes, there are holiday rentals close to the most popular sights in Hillsborough, or you can select a more secluded option if you're looking for a relaxing 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.

How many holiday rentals are there in Hillsborough?

With 4 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Tyrell Bay Beach and Chatham Bay Beach.

What’s a holiday rental in Hillsborough like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Hillsborough. Holiday rentals feature amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a family trip or a small group gathering.

Recent reviews of Hillsborough properties
Expedia verified reviews