Hillsborough holiday homes

We found 14 holiday rentals — enter your dates for availability

Discover a selection of 5 villas and other holiday rentals in Hillsborough that are perfect for your trip. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as Wi-Fi and a washer and dryer. Whatever you're looking for, you're sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

The secluded area of Hillsborough awaits your stay

The beaches and gardens provide a pleasant backdrop to your holiday home in Hillsborough. Renowned for its snorkelling, hiking and boating, this city welcomes all visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Exploring the natural features in Hillsborough

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Hillsborough is a great place to get outside. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Sandy Island (1.7 mi / 2.8 km)
  • Chatham Bay Beach (8.3 mi / 13.4 km)
  • Tobago Cays (12.2 mi / 19.7 km)
  • Anse La Roche Beach (2.5 mi / 4 km)
  • Tyrell Bay Beach (2.8 mi / 4.5 km)
  • Mopion (6 mi / 9.7 km)

Seasonal weather averages in Hillsborough

If you're hoping to enjoy some warm-weather activities on your holiday, September, October, August and November are the hottest months to visit, when temperatures average 28°C.

Transport to and around Hillsborough

The nearest airport is in Canouan Island (CIW), located 16.7 mi (26.8 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into St. George's (GND-Maurice Bishop Intl.), which is 39.8 mi (64.1 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Hillsborough?
The most sought-after types of holiday homes in Hillsborough are villas. Prefer something different? Bookabach has plenty of options to match our guests’ requirements, so you’ll see holiday homes in lots of sizes and shapes. The perfect home away from home is waiting for you — find yours today.
How much does it cost to rent a holiday home in Hillsborough?
The average price for a holiday home in Hillsborough depends on several factors, such as season, length of stay and property type. Whether you’re searching for a sprawling villa with a pool or a comfy cabin just for the two of you, just enter your travel dates to discover stays that offer great value.
How much does it cost to rent a beach house in Hillsborough?
Prices for beach houses in Hillsborough will vary depending on the style and size of the property and time of year you’re travelling. Simply enter your dates of travel into Bookabach and the number of guests to view your options and prices. From there you can use our filter tool to narrow your search results by nearby activities, amenities, ratings and more.
Are there pet-friendly holiday homes in Hillsborough?
Pack a squeezy toy and a bone for your pooch because Hillsborough has eight stays that welcome pets with open arms. Let your happy hound enjoy the family fun at one of our pet-friendly holiday homes on Bookabach. Simply enter your dates and destination, then check our “Pets allowed” filter box.
Can I rent a house with a pool in Hillsborough?
Tick the “pool” box in our filter tool and pick from three houses with private pools in Hillsborough on Bookabach. Morning soak, afternoon splash or midnight swim? Leisure time is up to you when your holiday property has its own pool.
What are popular home amenities in Hillsborough?
Some of the most popular home amenities people prefer in Hillsborough are a beach view, a firepit and an ocean view. Whether you’re taking a trip with family, friends or even pets, Bookabach holiday properties feature the best amenities for hanging out with your loved ones.
Are there large group holiday homes in Hillsborough?
With seven Hillsborough holiday properties that can accommodate five or more people, you can invite a few extra friends or family members along. Whether you’re planning a casual gathering or a special event, we’ll help you find a comfy space to fit the occasion.
Are there holiday homes in Hillsborough that welcome kids?
Hillsborough has eight family-friendly holiday homes. And tracking down a stay that welcomes kids is easy with Bookabach’s “Properties good for families” filter. As well as having the whole place to yourselves, you’ll also get access to conveniences and perks like dining rooms, yards and private pools.
What are the top attractions for families in Hillsborough?
You’ll find lots of amazing things to do and see with the family in Hillsborough, including:

  • Anse La Roche Beach
  • Carriacou Museum
  • Sandy Island

Can I find two-bedroom holiday homes in Hillsborough?
Gather your loved ones and enjoy a relaxing escape in one of the five two-bedroom holiday properties Hillsborough has to offer.
Are there holiday homes with WiFi in Hillsborough?
Hillsborough has four holiday homes with WiFi, so you’ll be able to stay connected while travelling. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming TV shows with the family to posting pics on social media, these Bookabach homes make it a cinch to get online.
How old do you have to be to rent a holiday home in Hillsborough?
The minimum age allowed can vary across properties on Bookabach, so double-check the rules of the holiday home in Hillsborough you’re interested in. But in general, it’s 16, 18 or 21.
How long can I rent a holiday home in Hillsborough for?
It’s really down to the Hillsborough property. To see all available options offering extended stays, just type your dates and guest number into the Bookabach search page. You can look forward to having the place to yourself, as well as comforts such as a full kitchen, air conditioning and a backyard to play in. Be on the lookout for any long-term stays that offer discounted weekly or monthly prices.

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