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.
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Price was CA $2,976, price is now CA $2,746 per person
CA $2,746
per person
Sep 13 - Sep 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to The Valley (AXA)
8.2/10 Very good! (330 reviews)
The location is excellent, just a few steps to the beach. The people are very friendly and nice, always helpful and ready to help out. My room was clean and spacious, good size bathroom, great balcony. Next time I will book a room with sea view, in general the grounds could get a little TLC.

Reviewed on Jun 21, 2026

Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Price was CA $6,960, price is now CA $4,344 per person
CA $4,344
per person
Aug 6 - Aug 13
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to The Valley (AXA)
9.6/10 Exceptional! (199 reviews)
Aurora is the old Cuisinart. This property has been exceptionally well maintained with the fabulous staff, a friendly and courteous team members. Anguilla is not the Island to go to if you’re looking for the Saint Barts overly expensive nightlife. This is the cool island. No cruise ships nothing ostentatious. Just a friendly safe place to enjoy a true relaxing vacation on some of the most wonderful beaches in the world. Aurora‘s location is fantastic at rendezvous Bay. It’s one of the best beaches in the world. Awesome food, and again great staff. The only negative and this is a very small one as they need new cushions on the chairs on the beach. The rooms, the facilities, the towels, everything right down to the sheets was spectacular.

Reviewed on Jun 7, 2026

Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Price was CA $4,630, price is now CA $4,130 per person
CA $4,130
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to The Valley (AXA)
9.4/10 Exceptional! (99 reviews)
This was the cleanest and most wonderful property I have stayed at yet. Tremendous compliments to the team.

Reviewed on Jun 27, 2026

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 $10,149, price is now CA $9,125 per person
CA $9,125
per person
Sep 13 - Sep 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to The Valley (AXA)
No reviews

6 BR Villa With Concierge Amenities Pool

6 BR Villa With Concierge Amenities Pool

2 out of 5
Price was CA $10,149, price is now CA $9,125 per person
CA $9,125
per person
Sep 13 - Sep 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to The Valley (AXA)
No reviews

Ready to book your vacation to South Hill?

 

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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 $272 per night from Jul 17 to Jul 18
CA $272
CA $360 total
Jul 17 - Jul 18
includes taxes & fees
9/10 Wonderful! (253 reviews)
"Great central location, great views especially from the dining area. We asked for an umbrella to add to the table on our balcony and staff were helpful and accommodating."

Reviewed on Jul 2, 2026

La Vue Boutique Inn
Royal Palms Hotel

Royal Palms Hotel

3.5 out of 5
West End South Hill
The price is CA $213 per night from Jul 12 to Jul 13
CA $213
CA $271 total
Jul 12 - Jul 13
includes taxes & fees
9/10 Wonderful! (72 reviews)
"Mary was very attentive, easy check in"

Reviewed on Jun 26, 2026

Royal Palms Hotel
Charming 1-bedroom villa in wonderful South Hill with AC, WiFi

Charming 1-bedroom villa in wonderful South Hill with AC, WiFi

South Hill Anguilla
8.8/10 Excellent! (5 reviews)
"Friendly and welcoming staff greeted us and checked in on us daily. Responsive to questions"

Reviewed on Apr 15, 2026

Get rates
Charming 1-bedroom villa in wonderful South Hill with AC, WiFi
See all 366 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.
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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 $2,746 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.

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