Upper Carolina Vacation Packages

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Top Holiday Package Deals in Upper Carolina

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 20 hours 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

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 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Thomas (STT)
9.2/10 Wonderful! (33 reviews)
Limetree Beach Resort by Club Wyndham

Limetree Beach Resort by Club Wyndham

3.5 out of 5
Price was CA $3,638, price is now CA $2,588 per person
CA $2,588
per person
Nov 1 - Nov 8
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) 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

Calichi at Picture Point

Calichi at Picture Point

4 out of 5
Price was CA $4,947, price is now CA $3,933 per person
CA $3,933
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Thomas (STT)
9.8/10 Exceptional! (71 reviews)
Absolutely incredible! Stunning, breathtaking views! Tiffany was great with communication. Most perfect spot for our 10 year anniversary! Quiet, peaceful, secluded mountain top resort. 10/10 recommend!

Reviewed on Aug. 23, 2025

Virgin Islands Campground

Virgin Islands Campground

2 out of 5
Price was CA $1,706, price is now CA $1,450 per person
CA $1,450
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Thomas (STT)
9.4/10 Exceptional! (115 reviews)
I thoroughly enjoyed my stay at the Camp grounds! This trip was a solo trip for me and I used it just for a little me time. Great place to relax and do exactly nothing. The cabin was nice and cozy. Open to nature and you will hear it as you rest and relax. I realize no place is perfect and perfection was not what I was in need for. This place was more for self therapy and peace. I would do it again if possible or if my health allows

Reviewed on May 6, 2025

Where to stay in Upper Carolina

Find the best Upper Carolina areas and neighborhoods for the activities you enjoy most. Learn more about Upper Carolina
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

Upper Carolina 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 $322 per night from Sep 1 to Sep 2
CA $322
CA $363 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 $345 per night from Sep 26 to Sep 27
CA $345
CA $501 total
Sep 26 - Sep 27
includes taxes & fees
8.2/10 Very Good! (1,010 reviews)
"Everything was amazing at the hotel especially the staff."

Reviewed on Aug. 22, 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 $234 per night from Aug 28 to Aug 29
CA $234
CA $286 total
Aug 28 - Aug 29
includes taxes & fees
Windward Passage Hotel
See all 3,702 properties in Upper Carolina
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 an Upper Carolina vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Upper Carolina from just CA $1,442. And the more you bundle, the more money you save. Your dream vacation has never been more affordable.
How do I get a cheap travel package to Upper Carolina?
Bundle your hotels and flights with Expedia to save on your next getaway. With more than 550 partner airlines and 1,000,000 hotel options across the world, your Upper Carolina vacation package can be customized exactly to suit your budget. With all that extra money, why not add one or two interesting experiences and tours? It's an easy way to unlock even more savings. That dream vacation to Upper Carolina is closer than you thought!
Where should I stay in Upper Carolina?
Upper Carolina is home to a number of interesting places to discover, like Ajax Peak. Lock in a hotel close by and make sightseeing a breeze.
What are the top hotels in Upper Carolina?
Book a room at Magical Mystic Ridge, 10 Min To North Shore Beachs. It's one of the neighborhood's most popular hotels. Another highly rated option in Upper Carolina is Endless Views From This Perfect Pool Villa Just Minutes From Maho Bay.
How far in advance should I book my Upper Carolina vacation?
Reserving your spot early with Expedia means one less thing to worry about. Most carriers advertise prices up to 12 months prior to take off. This is generally the cheapest time to book. If circumstances have left you booking late, discount tickets to Upper Carolina sometimes occur just a few weeks before departure.
What does an Expedia Upper Carolina travel package include?
Expedia has everything you need to lock in Upper Carolina trip, but how you structure your package is up to you. Select from a combination of hotels, flights and rental cars. After some activities to keep you on the move? Once you've made your booking, you can add them on too. No matter your style or budget, there's a package deal to suit your needs.
What should I know before booking an Upper Carolina travel package?
Get ready to save with an Expedia travel package. Combine your flights, rental cars and hotels and land great discounts. You're not restricted to hotels, however. Book with us and select from beachside condos, cabins in the mountains and everything in between!
Can I choose my airline with an Upper Carolina Expedia vacation package?
You can, and with over 550 airlines to select from globally, you have loads of choice. Look through the available options and find out which airline suits your needs and budget.
If I'm not able to travel, can I cancel my Upper Carolina vacation package?
Because we know life can be unpredictable, the answer is yes. For further details, check out our Customer Service Portal. But generally speaking, if you've made your booking in the last 24 hours, you may be able to change or cancel it free of charge. Your hotel, airline or car rental company may charge a fee if your booking is older than that.

Things to do

St John Island and Trunk Bay Beach Tour From St Thomas

St John Island and Trunk Bay Beach Tour From St Thomas

CA $110
per traveller
St John Island and Trunk Bay Beach Tour From St Thomas
St John Island and Trunk Bay Beach Tour

St John Island and Trunk Bay Beach Tour

CA $103
per traveller
St John Island and Trunk Bay Beach Tour
St John Island Sightseeing Tour from St John

St John Island Sightseeing Tour from St John

CA $95
per adult
St John Island Sightseeing Tour from St John
See all activities in St. John
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.