Upper Carolina Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    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.
Two Sandals – A Boutique Hotel

Two Sandals – A Boutique Hotel

3.5 out of 5
Price was CA $2,247, price is now CA $1,645 per person
CA $1,645
per person
Apr 26 - May 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
8.8/10 Excellent! (469 reviews)
Our stay at Two Sandals – A Boutique Hotel was absolutely amazing. From the moment we arrived, the staff made us feel welcomed and genuinely cared for. Their energy, professionalism, and kindness truly set this place apart. Every question we had was answered with a smile, and they went above and beyond to make sure our stay was perfect. The hotel itself is beautiful — peaceful, clean, and felt like a true home away from home. Our room was spotless, comfortable, and thoughtfully prepared. What really touched me was how the staff helped with a last-minute decoration request — they made it happen so effortlessly and made the experience even more special. If you’re looking for a boutique stay with outstanding service and a relaxing atmosphere, this is it. I would absolutely stay here again!

Reviewed on Feb 17, 2026

Club Wyndham Elysian Beach Resort

Club Wyndham Elysian Beach Resort

3.5 out of 5
Price was CA $3,194, price is now CA $2,219 per person
CA $2,219
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to St. Thomas (STT)
7.8/10 Good! (173 reviews)
Chaniesha and her team that work their was so polite and kind I love the experience I’m coming back .

Reviewed on Oct 31, 2025

Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
Price was CA $2,871, price is now CA $2,004 per person
CA $2,004
per person
Apr 26 - May 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
8/10 Very Good! (2,299 reviews)
El hotel muy lindo. Cuarto espacioso y limpio.

Reviewed on Feb 21, 2026

Limetree Beach Resort by Club Wyndham

Limetree Beach Resort by Club Wyndham

3.5 out of 5
Price was CA $2,781, price is now CA $1,978 per person
CA $1,978
per person
Apr 26 - May 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
8.2/10 Very Good! (202 reviews)
Super clean, staff was really nice. Loved that the pool closed at 10pm. Food was really good.

Reviewed on Jan 17, 2026

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 $4,316, price is now CA $3,299 per person
CA $3,299
per person
Apr 26 - May 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
9.2/10 Wonderful! (33 reviews)

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 $291 per night from Mar 24 to Mar 25
CA $291
CA $391 total
Mar 24 - Mar 25
includes taxes & fees
8.8/10 Excellent! (93 reviews)
Clean room, staff was very helpful and friendly. The view of the island is beautiful from the resort.

Reviewed on Feb 18, 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 $762 per night from Feb 23 to Feb 24
CA $762
CA $857 total
Feb 23 - Feb 24
includes taxes & fees
7.8/10 Good! (2,366 reviews)
The grounds and room were gorgeous. Staff were mostly courteous, however the restaurant staff were not kind at times and were not organized.

Reviewed on Feb 17, 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 $1,088 per night from Mar 1 to Mar 2
CA $1,088
CA $1,353 total
Mar 1 - Mar 2
includes taxes & fees
8.2/10 Very Good! (1,095 reviews)
Beautiful property. Room was cleaned well daily. Service was terrible at the pool restaurant. We paid a high daily rate for a room that was basically in the basement. Chickens and roosters were very loud and aggressive.

Reviewed on Feb 18, 2026

The Westin St. Thomas Beach Resort & Spa
See all 3,708 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
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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 $1,645. 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. Thomas: Guided Sea Lion Encounter

St. Thomas: Guided Sea Lion Encounter

CA $162
per adult
100% of travellers recommend
St. Thomas: Guided Sea Lion Encounter
Snorkel Cat All Inclusive Adventure - 9:45 am

Snorkel Cat All Inclusive Adventure

CA $239
per adult
94% of travellers recommend
Snorkel Cat All Inclusive Adventure
St. John Full-Day Lime Out Snorkel Taco Lunch & Open Bar - Westin

St. John Full-Day Lime Out Snorkel Taco Lunch & Open Bar - Westin

CA $244
per adult
96% of travellers recommend
St. John Full-Day Lime Out Snorkel Taco Lunch & Open Bar - Westin
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.