Skytop Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 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.
Two Sandals – A Boutique Hotel

Two Sandals – A Boutique Hotel

3.5 out of 5
Price was CA $2,746, price is now CA $2,066 per person
CA $2,066
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to St. Thomas (STT)
8.8/10 Excellent! (469 reviews)
Our room was very large (Newport Room) and clean. The sofa could be replaced, the bed was comfortable and it was quiet around there. We had a view of RedHook Marina. A full, delicious breakfast was served to us on the deck each morning. The ladies were super sweet. Water pressure was low. Overall a great stay.

Reviewed on Feb 1, 2026

The Breeze St Thomas

The Breeze St Thomas

2 out of 5
Price was CA $2,769, price is now CA $2,120 per person
CA $2,120
per person
Mar 25 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
No reviews
The Saint Resort

The Saint Resort

3 out of 5
Price was CA $5,751, price is now CA $4,436 per person
CA $4,436
per person
Mar 29 - Apr 5
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
9.4/10 Exceptional! (23 reviews)
Clean room and facilities, friendly staff, peaceful setting. We had a great time and hope to return someday!

Reviewed on Jan 14, 2026

The Hideaway Hull Bay

The Hideaway Hull Bay

4 out of 5
Price was CA $7,763, price is now CA $6,063 per person
CA $6,063
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to St. Thomas (STT)
9.6/10 Exceptional! (54 reviews)
The room was incredible and the grounds beyond amazing. The property is a few steps from Hull Bay beach and the restaurant’s food is delicious. Highly recommend!

Reviewed on Jan 26, 2026

St John Inn

St John Inn

3 out of 5
Price was CA $3,233, price is now CA $2,586 per person
CA $2,586
per person
Mar 16 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to St. Thomas (STT)
9.2/10 Wonderful! (413 reviews)
St. John in never disappoints! From the clean rooms, to helpful staff it is alway a pleasure staying there. Rum punch happy hour & breakfast are always great! Love this place!

Reviewed on Feb 1, 2026

Where to stay in Skytop

Find the best Skytop areas and neighborhoods for the activities you enjoy most. Learn more about Skytop
Cinnamon Bay featuring tropical scenes and a sandy beach

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 $285 per night from Feb 10 to Feb 11
CA $285
CA $384 total
Feb 10 - Feb 11
includes taxes & fees
8.6/10 Excellent! (62 reviews)
Room was clean but had strong scent of cleaning chemicals. Location is best with a car. We did not have a car and could walk to town and cruise ship area, but coming back at night it’s best to use a taxi as the immediate area at the bottom of the hill is not well lit. Nice pool and bar area overlooking ...

Reviewed on Feb 5, 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
The price is CA $651 per night from Feb 10 to Feb 11
CA $651
CA $732 total
Feb 10 - Feb 11
includes taxes & fees
7.8/10 Good! (2,357 reviews)
Rooms were nice & spacious. Helpful staff

Reviewed on Feb 5, 2026

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 $991 per night from Feb 11 to Feb 12
CA $991
CA $1,243 total
Feb 11 - Feb 12
includes taxes & fees
8.2/10 Very Good! (1,072 reviews)
Clean room. Excellent service. Friendly helpful staff.

Reviewed on Feb 5, 2026

The Westin St. Thomas Beach Resort & Spa
See all 3,745 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 $2,066. 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.