Upper Carolina Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in Upper Carolina

Price found within the past 48 hours. Click for updated prices.
Hotel 1829

Hotel 1829

4.5 out of 5
Price was CA $2,891, price is now CA $2,209 per person
CA $2,209
per person
May 25 - May 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
9.8/10 Exceptional! (17 reviews)
Air conditioning kept the room cool Our room was clean and comfortable. And we had a great meal at the restaurant on site. They did not offer any items that you may need for sale water as such. We would stay again. Hotels pretty neat being so old. Staff was exceptional

Reviewed on Mar 16, 2026

Villa Island Paradise

Villa Island Paradise

4 out of 5
Price was CA $3,530, price is now CA $2,727 per person
CA $2,727
per person
Apr 24 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to St. Thomas (STT)
9.4/10 Exceptional! (18 reviews)
Property was beautiful and loved the location. We were able to walk to a grocery store and restaurants. View was amazing and the decor was very boho. Loved it!

Reviewed on Mar 8, 2026

Calichi at Picture Point

Calichi at Picture Point

4 out of 5
Price was CA $5,826, price is now CA $4,513 per person
CA $4,513
per person
May 11 - May 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to St. Thomas (STT)
9.8/10 Exceptional! (80 reviews)
Gorgeous property. Amazing views. Well furnished. Great communication. Property management went out of their way for the little extras to make it a most memorable experience.

Reviewed on Feb 26, 2026

Limetree Beach Resort by Club Wyndham

Limetree Beach Resort by Club Wyndham

3.5 out of 5
Price was CA $2,950, price is now CA $2,296 per person
CA $2,296
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to St. Thomas (STT)
8.2/10 Very Good! (210 reviews)
Staff was excellent. Property an outdoor amenities like pool area were also great. Only negative was the Wi-Fi was extremely spotty, especially in the room.

Reviewed on Mar 18, 2026

Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
Price was CA $3,366, price is now CA $2,625 per person
CA $2,625
per person
Apr 24 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to St. Thomas (STT)
8/10 Very Good! (2,395 reviews)
Beautiful views, clean, helpful staff!

Reviewed on Mar 22, 2026

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 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

Upper Carolina 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 $355 per night from Apr 21 to Apr 22
CA $355
CA $478 total
Apr 21 - Apr 22
includes taxes & fees
9/10 Wonderful! (163 reviews)
There isn’t an airport shuttle, but the $20 a person taxi will take you there. The hill it sits on is steep, but you can walk it, we did several times. The staff is hit and miss, some are friendly, some make you feel like you’re a huge inconvenience to them (avoid the convenience store at all costs) ...

Reviewed on Mar 22, 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 $789 per night from Mar 24 to Mar 25
CA $789
CA $888 total
Mar 24 - Mar 25
includes taxes & fees
8/10 Very Good! (2,388 reviews)
Beautiful views, clean, helpful staff!

Reviewed on Mar 22, 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 $858 per night from Apr 19 to Apr 20
CA $858
CA $1,089 total
Apr 19 - Apr 20
includes taxes & fees
8.4/10 Very Good! (1,140 reviews)
Beautiful views of ocean all around the hotel. Stayed in Seacliff Tower - room was lovely, ocean view, comfy bed, rain shower head in bathroom. Recommend taking stairs as elevators can be slow. Employees always available in front of hotel to get you in the appropriate cab for where you want to go. ...

Reviewed on Mar 22, 2026

The Westin St. Thomas Beach Resort & Spa
See all 3,704 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
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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 $2,209. 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

Snorkel Cat All Inclusive Adventure - 9:45 am

Snorkel Cat All Inclusive Adventure

CA $219
per adult
94% of travellers recommend
Snorkel Cat All Inclusive Adventure
Saint Thomas: Shark Encounter at Coral World Ocean Park

Saint Thomas: Shark Encounter at Coral World Ocean Park

CA $88
per adult
88% of travellers recommend
Saint Thomas: Shark Encounter at Coral World Ocean Park
Lime Out

St. Thomas Lime Out Snorkel with Taco Bar Lunch & Swim-Up Bar - Ritz-Carlton

CA $259
per adult
84% of travellers recommend
St. Thomas Lime Out Snorkel with Taco Bar Lunch & Swim-Up Bar - Ritz-Carlton
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.