Hillsborough vacation rentals

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Discover a selection of 5 villas and other vacation rentals in Hillsborough that are perfect for your trip. Vacation homes provide the best amenities for your family, friends, or furry companion, such as parking and air conditioning. At the end of the day, you'll find a rental that has what everyone needs, including accessible or non-smoking choices.

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, yards and more
  • More for less
    More space, more privacy, more amenities — more value

The remote area of Hillsborough awaits your stay

The beaches and gardens provide a pleasant backdrop to your vacation home in Hillsborough. Renowned for its snorkeling, 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 an outdoor enthusiast or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Hillsborough. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • 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 vacation, September, October, August and November are the hottest months to visit, when temperatures average 83°F.

Transportation to and around Hillsborough

The nearest airport is in Canouan Island (CIW), located 16.7 mi (26.8 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Maurice Bishop Intl. Airport (GND), which is 39.8 mi (64.1 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Hillsborough?
The most sought-after types of vacation rentals in Hillsborough are villas. Prefer something different? Vrbo has plenty of options to match our guests’ requirements, so you’ll see vacation 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 vacation rental in Hillsborough?
The average price for a vacation 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 traveling. Simply enter your dates of travel into Vrbo 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 vacation rentals 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 vacation rentals on Vrbo. 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 Vrbo. Morning soak, afternoon splash or midnight swim? Leisure time is up to you when your vacation property has its own pool.
What are popular rental amenities in Hillsborough?
Some of the most popular rental 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, Vrbo vacation properties feature the best amenities for hanging out with your loved ones.
Are there large group vacation rentals in Hillsborough?
With seven Hillsborough vacation 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 vacation rentals in Hillsborough that welcome kids?
Hillsborough has eight family-friendly vacation homes. And tracking down a stay that welcomes kids is easy with Vrbo’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 vacation rentals in Hillsborough?
Gather your loved ones and enjoy a relaxing escape in one of the five two-bedroom vacation properties Hillsborough has to offer.
Are there vacation rentals with WiFi in Hillsborough?
Hillsborough has four vacation rentals with WiFi, so you’ll be able to stay connected while traveling. 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 Vrbo homes make it a cinch to get online.
How old do you have to be to rent a vacation rental in Hillsborough?
The minimum age allowed can vary across properties on Vrbo, so double-check the rules of the vacation home in Hillsborough you’re interested in. But in general, it’s 16, 18 or 21.
How long can I rent a vacation rental 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 Vrbo 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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