Upper Carolina Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Eric Sturgeon

  • 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 Upper Carolina

Price found within the past 48 hours. Click for updated prices.
At Home in the Tropics

At Home in the Tropics

3 out of 5
Price was CA $2,369, price is now CA $1,566 per person
CA $1,566
per person
Apr 21 - Apr 28
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
9.8/10 Exceptional! (149 reviews)
Very nice stay and close to eveerything.

Reviewed on Jan 31, 2026

Limetree Beach Resort by Club Wyndham

Limetree Beach Resort by Club Wyndham

3.5 out of 5
Price was CA $3,551, price is now CA $2,361 per person
CA $2,361
per person
Apr 21 - Apr 28
found 11 hours 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 $6,955, price is now CA $4,748 per person
CA $4,748
per person
Apr 11 - Apr 18
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to St. Thomas (STT)
9.2/10 Wonderful! (33 reviews)
Club Wyndham Elysian Beach Resort

Club Wyndham Elysian Beach Resort

3.5 out of 5
Price was CA $4,232, price is now CA $2,931 per person
CA $2,931
per person
Apr 11 - Apr 18
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) 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 $3,619, price is now CA $2,551 per person
CA $2,551
per person
Apr 11 - Apr 18
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to St. Thomas (STT)
8/10 Very Good! (2,299 reviews)
Rooms were good. No view and constant weed smoking that kept you off the deck. But yhe most irritating was the woman pushing to get you to attend time share. Total pressure job. Almost left.

Reviewed on Feb 7, 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

Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
6080 Estate Smith Bay St. Thomas
The price is CA $688 per night from Feb 9 to Feb 10
CA $688
CA $774 total
Feb 9 - Feb 10
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
Bluebeard's Castle Resort

Bluebeard's Castle Resort

4 out of 5
1331 Estate Taarneberg Charlotte Amalie Saint Thomas
The price is CA $286 per night from Feb 10 to Feb 11
CA $286
CA $385 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
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 28 to Mar 1
CA $991
CA $1,243 total
Feb 28 - Mar 1
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 3,735 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 $1,566. 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 Full-Day Lime Out Snorkel Taco Lunch & Open Bar - Westin

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

CA $249
per adult
96% of travellers recommend
St. John Full-Day Lime Out Snorkel Taco Lunch & Open Bar - Westin
Snorkel Cat All Inclusive Adventure - 9:45 am

Snorkel Cat All Inclusive Adventure

CA $243
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 $89
per adult
88% of travellers recommend
Saint Thomas: Shark Encounter at Coral World Ocean Park
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.