South Hill Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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 $2,191, price is now CA $1,951 per person
CA $1,951
per person
Aug 23 - Aug 29
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to The Valley (AXA)
9.2/10 Wonderful! (119 reviews)
Staff was very helpful and kind. The photos online are incredibly incredibly misleading with regard to the look and feel of the location, as well as the actual hotel. Two power interruptions over the course of the two days of being there, the second off for several hours, and that came the day of checkout which meant I couldn’t make breakfast or warm up any food for my son before we traveled. That was quite frustrating for me. However, the room was spacious, with plenty of room to move around.

Reviewed on Jul 15, 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 $14,495, price is now CA $12,198 per person
CA $12,198
per person
Sep 5 - Sep 12
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to The Valley (AXA)
No reviews

Paradise Cove Resort

Paradise Cove Resort

2.5 out of 5
Price was CA $3,585, price is now CA $3,303 per person
CA $3,303
per person
Sep 5 - Sep 12
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to The Valley (AXA)
8/10 Very good! (47 reviews)
Great staff. Spacious and very clean rooms. Must have a car. In between seasons, yacuzzi nor hot tubs were operational (waiting for parts).

Reviewed on Mar 28, 2026

Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Price was CA $3,175, price is now CA $3,031 per person
CA $3,031
per person
Sep 5 - Sep 12
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to The Valley (AXA)
8.2/10 Very good! (331 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

6 BR Villa With Concierge Amenities Pool

6 BR Villa With Concierge Amenities Pool

2 out of 5
Price was CA $10,873, price is now CA $9,446 per person
CA $9,446
per person
Aug 23 - Aug 29
found 7 hours ago
Roundtrip flight included
Toronto (YTO) 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 $268 per night from Aug 11 to Aug 12
CA $268
CA $355 total
Aug 11 - Aug 12
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 $210 per night from Jul 23 to Jul 24
CA $210
CA $267 total
Jul 23 - Jul 24
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 $168 per night from Jul 21 to Jul 22
CA $168
CA $196 total
Jul 21 - Jul 22
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 369 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 $1,951 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.

Explore a world of travel with Expedia

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