Upper Carolina Vacation Packages

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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.
Windward Passage Hotel

Windward Passage Hotel

3.5 out of 5
per person
Oct 18 - Oct 22
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
7/10 Good! (1,390 reviews)
I didn't like that TV has no good working channels and rooms doesn't have a microwave

Reviewed on Jul. 29, 2025

At Home in the Tropics

At Home in the Tropics

3 out of 5
per person
Aug 30 - Sep 6
found 4 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Thomas (STT)
9.8/10 Exceptional! (145 reviews)
The property managers made me feel very welcomed and this property stays locked so me and my girlfriend felt very safe the entire trip. Planning on saving more money and will come back to visit asap. Would recommend to anyone and everyone visiting st Thomas

Reviewed on Jul. 21, 2025

Club Wyndham Elysian Beach Resort

Club Wyndham Elysian Beach Resort

3.5 out of 5
per person
Oct 18 - Oct 22
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
7.6/10 Good! (156 reviews)
Location is not bad, but is not wakable at surroundings area. A trolley to redhook could be a great option if available. The beach bistro Sangrias, if they open until at least 10 or 11pm can give guests a great alternative ro stay at rhe hotel instead of going out.

Reviewed on Jul. 6, 2025

Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
per person
Oct 18 - Oct 22
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
8.2/10 Very Good! (2,096 reviews)
The property it’s self is

Reviewed on Jul. 31, 2025

Limetree Beach Resort by Club Wyndham

Limetree Beach Resort by Club Wyndham

3.5 out of 5
per person
Sep 16 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Thomas (STT)
8.4/10 Very Good! (186 reviews)
Great resort. I chose it for having both ocean access and a great pool. The room was spacious for myself and two teens. Also, having a full size refrigerator AND laundry facilities available is also a huge perk!

Reviewed on Jul. 27, 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

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
The price is CA $483 per night from Aug 30 to Aug 31
CA $483
CA $659 total
Aug 30 - Aug 31
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
"Very nice hotel , could’ve stayed at a cheaper hotel and got the same experience gratuity is charged everytime u swipe ur card . The food options are limited after hours as everything shuts down by 10… if your a smoker this ain’t the place lol… property is well kept for the most part .. everyone ..."

Reviewed on Jul. 30, 2025

The Westin St. Thomas Beach Resort & Spa
Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
6080 Estate Smith Bay, St. Thomas
The price is CA $497 per night from Aug 5 to Aug 6
CA $497
CA $559 total
Aug 5 - Aug 6
includes taxes & fees
8/10 Very Good! (2,150 reviews)
"Wonderful stay. The seasonal seaweed flock smell was awful, preventing dining by the water, but out of your control. Appreciated the no extra fee for use of the washing machine and dryer. Loved seeing the stray chickens, cats, and dogs, that visited daily. Please get the cats and dogs vaccinated ..."

Reviewed on Jul. 28, 2025

Margaritaville Vacation Club - St. Thomas
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 $248 per night from Aug 1 to Aug 2
CA $248
CA $304 total
Aug 1 - Aug 2
includes taxes & fees
6.8/10 (1,402 reviews)
"I didn't like that TV has no good working channels and rooms doesn't have a microwave"

Reviewed on Jul. 29, 2025

Windward Passage Hotel
See all 3,746 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.
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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 $1,083. 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 $109
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 $102
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 $94
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.