Skytop Vacation Packages

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Top Holiday Package Deals in Skytop

Price found within the past 48 hours. Click for updated prices.
Pirates Pension at Bluebeard's Castle

Pirates Pension at Bluebeard's Castle

3 out of 5
Price was CA $1,847, price is now CA $1,442 per person
CA $1,442
per person
Nov 19 - Nov 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to St. Thomas (STT)
8.4/10 Very Good! (744 reviews)
Nice place for the price. Only thing rent a car. Taxis add up

Reviewed on Aug. 27, 2025

Limetree Beach Resort by Club Wyndham

Limetree Beach Resort by Club Wyndham

3.5 out of 5
Price was CA $2,472, price is now CA $1,666 per person
CA $1,666
per person
Oct 14 - Oct 21
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
8.2/10 Very Good! (194 reviews)
Room very cute and accommodating. Me and my husband brought our 21 yr old daughter and it was nice that our king size bed was in the loft area so our daughter had the downstairs area with the pull out sofa and balcony to give her space as well. The only negative of the room was the carpet had a couple of stains that should have been treated/cleaned.

Reviewed on Aug. 18, 2025

Great Bay Condominiums located at The Ritz-Carlton Club, St Thomas

Great Bay Condominiums located at The Ritz-Carlton Club, St Thomas

4.5 out of 5
Price was CA $4,255, price is now CA $2,997 per person
CA $2,997
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Thomas (STT)
9.2/10 Wonderful! (33 reviews)
Hilltop Villas at Bluebeard's Castle

Hilltop Villas at Bluebeard's Castle

3 out of 5
Price was CA $1,927, price is now CA $1,545 per person
CA $1,545
per person
Nov 19 - Nov 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to St. Thomas (STT)
8.6/10 Excellent! (1,712 reviews)
The room was clean, spacious and we loved the view of the bay. The ladies at the front desk were nice and gave us suggestions on where to dine. Also Tevin at the entrance was extremely nice.

Reviewed on Aug. 26, 2025

Sapphire Sanctuary by the Sea

Sapphire Sanctuary by the Sea

3 out of 5
Price was CA $2,062, price is now CA $1,662 per person
CA $1,662
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Thomas (STT)
9/10 Wonderful! (44 reviews)
The property was very nice, we had everything we needed. We appreciated that there were restaurants available if we didn’t choose to drive anywhere. The beach was beautiful and it was so convenient that there were lounge chairs available on the beach.

Reviewed on Jul. 14, 2025

Where to stay in Skytop

Find the best Skytop areas and neighborhoods for the activities you enjoy most. Learn more about Skytop
Cinnamon Bay showing forest scenes

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

Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
6080 Estate Smith Bay, St. Thomas
The price is CA $321 per night from Sep 1 to Sep 2
CA $321
CA $361 total
Sep 1 - Sep 2
includes taxes & fees
8/10 Very Good! (2,201 reviews)
"Loved everything about it , especially the breakfast in the store"

Reviewed on Aug. 23, 2025

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, Po Box 7100, St. Thomas, St. Thomas
Fully refundableReserve now, pay when you stay
The price is CA $344 per night from Sep 11 to Sep 12
CA $344
CA $499 total
Sep 11 - Sep 12
includes taxes & fees
8.2/10 Very Good! (1,025 reviews)
"The property was beautiful and clean. Comfortable room with a beautiful view"

Reviewed on Aug. 25, 2025

The Westin St. Thomas Beach Resort & Spa
Windward Passage Hotel

Windward Passage Hotel

3.5 out of 5
Veterans Drive Charlotte Amali, Po Box 640, St. Thomas, St. Thomas
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from Aug 29 to Aug 30
CA $233
CA $285 total
Aug 29 - Aug 30
includes taxes & fees
7/10 Good! (1,380 reviews)
"Windward was a great choice for my stay on the beautiful Island of St Thomas. I've enjoyed the love resort stafff, amenities, free breakfast, convience of being able to walk and fulfil all of my shopping needs."

Reviewed on Aug. 27, 2025

Windward Passage Hotel
See all 3,709 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.
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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 $1,442. 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.