Southside Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$616 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

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

Our pick of the best Southside Hotel Deals

The Westin St. Thomas Beach Resort & Spa

The Westin St. Thomas Beach Resort & Spa

4.5 out of 5
5 Estate Bakkeroe St. Thomas St. Thomas
The price is NZ$1,381 per night from 28 Apr to 29 Apr
NZ$1,381
28 Apr - 29 Apr
includes taxes & fees
8.4/10 Very Good! (1,149 reviews)
Clean room. Swim up bar and infinity pool. Good drinks. Food was just okay.

Reviewed on 29 Mar 2026

The Westin St. Thomas Beach Resort & Spa
Hampton by Hilton St. Thomas

Hampton by Hilton St. Thomas

3 out of 5
Havensight Mall Parcel 2 Charlotte Amalie St. Thomas
Fully refundableReserve now, pay when you stay
The price is NZ$691 per night from 7 Apr to 8 Apr
NZ$691
7 Apr - 8 Apr
includes taxes & fees
8.8/10 Excellent! (119 reviews)
Room cleaning should be every day

Reviewed on 29 Mar 2026

Hampton by Hilton St. Thomas
Buoy Haus Beach Resort St. Thomas, Autograph Collection

Buoy Haus Beach Resort St. Thomas, Autograph Collection

3.5 out of 5
2 Estate Bakkeroe St. Thomas VI
The price is NZ$1,776 per night from 22 Apr to 23 Apr
NZ$1,776
22 Apr - 23 Apr
includes taxes & fees
9.4/10 Exceptional! (161 reviews)
Room and beach were great. The restaurants missed the mark.

Reviewed on 26 Mar 2026

Buoy Haus Beach Resort St. Thomas, Autograph Collection
See all 440 properties in Southside
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.

Frequently asked questions

How much does a Southside holiday package cost?
Get ready to book, because a trip to Southside starts from a tempting . When you combine your flights, hotels and car rentals into a travel package, you'll pick up great deals.
How do I get a cheap travel package to Southside?
Crafting your own Southside holiday package with Expedia is a smart way to save. We have access to more than 550 airlines and 1 000 000 properties across the globe. With such a wonderful range to pick from, you'll have no trouble putting together your next dream escape.
How far in advance should I book my Southside holiday?
It's tricky picking the ideal time for airfares, but we normally say the earlier, the better. Many international journeys on Expedia become available up to 12 months in advance. If you're booking late, don't worry. Discounted prices occasionally appear within a few weeks of departure dates.
What does an Expedia Southside travel package include?
It comes down to what type of escape you have in the works. Southside holiday deals can include car rentals, flights and hotels. You can mix and match to create the travel package that suits you. You can also add on experiences and activities after you've booked to get even bigger discounts.
What should I know before booking a Southside travel package?
Our prices are already low. However, you'll snap up even more savings if you book your hotels, flights and car rentals together. With an Expedia package, you'll always get transparent pricing and tons of choice.
Can I choose my airline with a Southside Expedia holiday package?
With a holiday package, you're always in charge. Whether you'd like to fly to Southside in coach or business class, simply select from the available airline options. Expedia has access to more than 550 airline partners worldwide.
If I'm not able to travel, can I cancel my Southside holiday package?
Your situation can change unexpectedly, so yes, you can. You may be able to amend or cancel your Southside holiday package at no cost within 24 hours of booking. For bookings older than that, you can still make the necessary changes, but your airline, hotel or car rental company may impose a charge. Want more information? Have a look at our Customer Service Portal. We'll help make sure your trip goes off without a hitch.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.