South Hill Vacation Packages

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Your South Hill Vacation

Lock in a South Hill vacation package and get ready for a wonderful adventure. Well known for its laid-back lifestyle and welcoming locals, there's plenty to love about this captivating city. You'll want to go sightseeing during your trip to South Hill. Drop by top attractions such as Maundays Bay, Anguilla Arch and Shoal Bay West. A few clicks is all it takes to create a tailor-made South Hill vacation on Expedia.

Top South Hill Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Coralito Bay Suites & Villas

Coralito Bay Suites & Villas

3.5 out of 5
Price was CA $3,644, price is now CA $3,304 per person
CA $3,304
per person
Sep 8 - Sep 14
found 6 hours ago
Roundtrip flight included
Montreal (YMQ) to The Valley (AXA)
10/10 Exceptional! (23 reviews)
Beautiful, clean accommodations for our first visit to the island. Perfect, central location to make exploring the island easy to accomplish on our 5 day trip. Although we only cooked breakfast, we appreciated the well stocked kitchen. Beds were very comfortable and the views from our porch of Saint Martin were amazing. Staff and host were all very helpful. Highly recommend.

Reviewed on Jul 19, 2026

Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Price was CA $7,427, price is now CA $5,407 per person
CA $5,407
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to The Valley (AXA)
9.6/10 Exceptional! (200 reviews)
Asian restaurant hostess was rude.

Reviewed on Jul 16, 2026

Carimar Beach Club

Carimar Beach Club

3.5 out of 5
Price was CA $3,861, price is now CA $3,683 per person
CA $3,683
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to The Valley (AXA)
9.4/10 Exceptional! (109 reviews)
Great location, clean and perfect beach!

Reviewed on Feb 23, 2026

6 BR Villa With Concierge Amenities Pool

6 BR Villa With Concierge Amenities Pool

2 out of 5
Price was CA $13,008, price is now CA $11,756 per person
CA $11,756
per person
Sep 8 - Sep 14
found 6 hours ago
Roundtrip flight included
Montreal (YMQ) to The Valley (AXA)
No reviews

6 BR Villa On Crocus Bay With Pool Concierge

6 BR Villa On Crocus Bay With Pool Concierge

2 out of 5
Price was CA $12,381, price is now CA $11,209 per person
CA $11,209
per person
Sep 8 - Sep 14
found 6 hours ago
Roundtrip flight included
Montreal (YMQ) to The Valley (AXA)
No reviews

Ready to book your vacation to South Hill?

 

Choose your dates

South Hill Hotel Deals

La Vue Boutique Inn

La Vue Boutique Inn

3.5 out of 5
Back Street South Hill
The price is CA $269 per night from Aug 24 to Aug 25
CA $269
CA $357 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (254 reviews)
"I loved everything about my stay, the staff was helpful and friendly. I highly recommend this place to stay"

Reviewed on Jul 18, 2026

La Vue Boutique Inn
Royal Palms Hotel

Royal Palms Hotel

3.5 out of 5
West End South Hill
The price is CA $211 per night from Jul 29 to Jul 30
CA $211
CA $268 total
Jul 29 - Jul 30
includes taxes & fees
Royal Palms Hotel
OUR STUDIO APARTMENTS COMES EQUIPPED WITH ALL ESSENTIAL NEED

OUR STUDIO APARTMENTS COMES EQUIPPED WITH ALL ESSENTIAL NEED

THE VALLEY
The price is CA $169 per night from Aug 12 to Aug 13
CA $169
CA $197 total
Aug 12 - Aug 13
includes taxes & fees
8.8/10 Excellent! (5 reviews)
"Wow, what an amazing spot! Incredible view, rooftop pool, very private, and located so anywhere you drive on the island is under 10 min away! Euston was so helpful, even met me at the ferry dock so i could follow him back to the property the first night. I highly recommend this rental, and will definitely ..."

Reviewed on Mar 10, 2026

OUR STUDIO APARTMENTS COMES EQUIPPED WITH ALL ESSENTIAL NEED
See all 370 properties in South Hill
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Frequently asked questions

How much does a South Hill vacation package cost?
You can pick up a vacation package to this destination from CA $3,304 on Expedia. However, how much your vacation to South Hill costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to South Hill?
May, September and October are great times to search for cheap South Hill vacation packages. Opting to travel in quieter periods means you can typically find better prices on hotels and flights.
How many days is enough for South Hill?
Allow around 4 days for your South Hill vacation in order to enjoy everything that makes this place special. Explore key areas, including Sandy Ground and Sandy Hill. Then tick off major sights like Maundays Bay and Rendezvous Bay Beach. With a good itinerary, you can keep busy with room for some downtime too. Want to go beyond South Hill? Consider fitting in an excursion or two.
How to find the best South Hill package deals?
Use Expedia's filters to find some tempting South Hill package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or browse for South Hill package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a South Hill vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually land a better deal than booking each component separately. And you'll still get the flexibility to create a personalized South Hill vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to South Hill?
If you have your South Hill travel dates confirmed, book as early as you can to bag some outstanding deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to South Hill?

  1. Choose your dates: What you want to do in South Hill and your preferred season can help you decide when to travel.
  2. Budget wisely: On top of the price of your accommodations, you should consider other expenses. These include transportation, flights and food. Also, set aside a little extra for unexpected costs that could arise during your trip to South Hill.
  3. Decide how many days away: Start by compiling a list of the activities and sights you want to experience in South Hill. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your accommodations and airfare: Once you've settled on your trip dates and duration, lock in the ideal South Hill vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.