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.
Edwards Guesthouse

Edwards Guesthouse

2.5 out of 5
Sandy Ground
Price was CA $1,769, price is now CA $1,635 per person
CA $1,635
per person
Aug 10 - Aug 13
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to The Valley (AXA)
9.2/10 Wonderful! (119 reviews)
We came from Sint Maarten and the guest house didn’t have any electricity we couldn’t even get to dinner party. The guest house is not maintained well spider webs all around mold. All around was like a junk yard. They say we checked out no one was there and there was no electricity again! Horrible just horrible don’t stay there!!!!! Worst resting place ever!!!!

Reviewed on Jul 6, 2026

Ceblue Luxury Villas

Ceblue Luxury Villas

5 out of 5
Price was CA $2,256, price is now CA $2,179 per person
CA $2,179
per person
Aug 20 - Aug 23
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to The Valley (AXA)
10/10 Exceptional! (7 reviews)
My husband and I absolutely loved our time at CeBlue! Latoya our concierge was amazing and the beach is beautiful! Only negative would be there isn’t much options for food when you go beginning of August as most places close for hurricane season. Latoya was able to help us find some amazing restaurants throughout the island though. We will be back

Reviewed on Aug 10, 2025

Genesis Residences

Genesis Residences

2.5 out of 5
Price was CA $3,274, price is now CA $2,963 per person
CA $2,963
per person
Aug 12 - Aug 18
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to The Valley (AXA)
9.8/10 Exceptional! (6 reviews)
Everything!

Reviewed on Jul 6, 2026

Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Price was CA $6,192, price is now CA $5,713 per person
CA $5,713
per person
Aug 12 - Aug 18
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to The Valley (AXA)
9.6/10 Exceptional! (254 reviews)
Beautiful property with great service and incredible views! We’ll be back!

Reviewed on Jul 9, 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 $11,671, price is now CA $10,852 per person
CA $10,852
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Montreal (YMQ) 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 $285 per night from Jul 24 to Jul 25
CA $285
CA $376 total
Jul 24 - Jul 25
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
9/10 Wonderful! (72 reviews)
"Mary was very attentive, easy check in"

Reviewed on Jun 26, 2026

Get rates
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 371 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
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a South Hill vacation package cost?
You can pick up a vacation package to this destination from CA $1,635 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.