Skytop 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

Top Holiday Package Deals in Skytop

Price found within the past 48 hours. Click for updated prices.
The Cottage at Villa Indigo

The Cottage at Villa Indigo

3 out of 5
Price was CA $2,744, price is now CA $2,210 per person
CA $2,210
per person
Jul 8 - Jul 15
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
8.8/10 Excellent! (15 reviews)
We got a true dose of the life experience on the island staying here. The entire experience was MAGICAL!!!! Me and my family will most definitely staying again when we come back

Reviewed on May 26, 2025

The Hideaway Hull Bay

The Hideaway Hull Bay

4 out of 5
Price was CA $8,104, price is now CA $5,787 per person
CA $5,787
per person
Jun 27 - Jul 4
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
9.6/10 Exceptional! (62 reviews)
What a tropical paradise! We were blown away by Hideaway! If you are looking for a private, family or couple getaway, this is the best place around! The simplicity might be a little less than what some want, but the stay met every one of our needs. The environment was beautiful and the beach was our favorite on the island! Little touches everywhere were not overlooked by my family.

Reviewed on Apr 12, 2026

Wharfside Village Hotel

Wharfside Village Hotel

3 out of 5
Price was CA $5,045, price is now CA $3,916 per person
CA $3,916
per person
Jun 27 - Jul 4
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
9.8/10 Exceptional! (173 reviews)
Beautiful and great location

Reviewed on May 11, 2026

Club Wyndham Elysian Beach Resort

Club Wyndham Elysian Beach Resort

3.5 out of 5
Price was CA $3,394, price is now CA $2,661 per person
CA $2,661
per person
Jun 27 - Jul 4
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
8/10 Very Good! (183 reviews)
The property is beautiful the staff was good. They don’t have everyday guest service: u have to call them if you need clean towels and toilet tissue or clean sheets. The service is not automatic like everywhere else that’s the only thing I didn’t like. Overall it is a very beautiful property

Reviewed on May 11, 2026

Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
Price was CA $3,145, price is now CA $2,512 per person
CA $2,512
per person
Jun 27 - Jul 4
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
8/10 Very Good! (2,435 reviews)
The resorts, room, pools were so clean. The staff was really friendly. W

Reviewed on May 16, 2026

Where to stay in Skytop

Find the best Skytop areas and neighborhoods for the activities you enjoy most. Learn more about Skytop
Maho Bay Quarter

Maho Bay Quarter

If you're spending some time in Maho Bay Quarter, Maho Beach and Cinnamon Bay Beach are top sights worth seeing.

Find hotels in Maho Bay Quarter

Skytop Hotel Deals

Bluebeard's Castle Resort

Bluebeard's Castle Resort

4 out of 5
1331 Estate Taarneberg Charlotte Amalie Saint Thomas
The price is CA $314 per night from May 31 to Jun 1
CA $314
CA $422 total
May 31 - Jun 1
includes taxes & fees
8.8/10 Excellent! (403 reviews)
Beautiful hotel excellent views.

Reviewed on May 16, 2026

Bluebeard's Castle Resort
Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
6080 Estate Smith Bay St. Thomas
8/10 Very Good! (2,450 reviews)
.

Reviewed on May 17, 2026

Get rates
Margaritaville Vacation Club - St. Thomas
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 CA $549 per night from Jun 16 to Jun 17
CA $549
CA $734 total
Jun 16 - Jun 17
includes taxes & fees
8.4/10 Very Good! (1,226 reviews)
We stayed here for our honeymoon and it did NOT disappoint!!!! We had an amazing ocean view. The room was well kept and housekeeping did an excellent job with daily cleaning! There were 3 pool, a hot tub and a cold pu

Reviewed on May 16, 2026

The Westin St. Thomas Beach Resort & Spa
See all 3,684 properties in Skytop
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 Skytop vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Skytop from just CA $2,210. And the more you bundle, the more money you save. Your dream escape has never been so affordable.
How do I get a cheap travel package to Skytop?
You'll save loads of cash if you bundle your flights, car rentals and hotels into a Skytop vacation package. Sometimes cheap means fewer options. But not with Expedia. We offer more than 550 air carriers and 1,000,000 hotels worldwide, which means you'll always have plenty of variety to choose from. Like to save even more? Add some exciting activities to your package deal and unlock even more discounts! After all, travel is about more than simply getting to your destination.
What are the top hotels in Skytop?
Lock in a room at Pool - National Park Views - Next The Sieben Hiking Trail. It's one of this neighborhood's most in-demand properties. Another highly rated option in Skytop is Villa Hermosa A Beautiful St. John Villa.
How far in advance should I book my Skytop vacation?
It's difficult to pick the ideal time for airfares, but we usually say the earlier, the better. Many international flights on Expedia become available up to a year in advance. If you're booking late, don't despair. Budget prices occasionally appear within a few weeks of departure dates.
What does an Expedia Skytop travel package include?
With Expedia, you can choose a combination of flights, car rentals and hotels to build your perfect Skytop package. Once you've made your booking, you can add on fun stuff like tours and activities. Don't forget — the more you bundle, the more dollars you'll save!
What should I know before booking a Skytop travel package?
So many places to go, so many things to see and do. With a package, you'll be able to cross more of them off your list. Bundle your flights, hotels and rental cars and score big savings.
Can I choose my airline with a Skytop Expedia vacation package?
Yes, you can. We have more than 550 partner airlines globally, so pick the carrier that best fits your budget and traveling style.
If I'm not able to travel, can I cancel my Skytop vacation package?
If your vacation plans in Skytop have been upended, it's comforting to know that you can cancel or amend your booking. If you made your booking less than 24 hours ago, you may be eligible for a refund. If your booking is older than that, your airline, hotel or car rental company may impose a fee. For more details, visit our Customer Service Portal.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.