Middle Region 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 Middle Region

Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was CA $2,374, price is now CA $1,240 per person
CA $1,240
per person
Apr 30 - May 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (973 reviews)
We enjoyed princess heights. Not super close to restaurants so keep that in mind. Being able to cook food for breakfast was a plus. Staff is very friendly and accommodating. Jetted tub was a highlight to end each day. Would be nice if there was a screen on balcony door so you could leave open without mosquitoes coming in. Bed was comfortable. Kitchen had essentials for cooking such as pans and dishware. Dish soap was appreciated.

Reviewed on Feb 23, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was CA $3,539, price is now CA $1,535 per person
CA $1,535
per person
Apr 30 - May 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,463 reviews)
Staff, amenities and staff perfect

Reviewed on Feb 25, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was CA $5,269, price is now CA $2,457 per person
CA $2,457
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Philipsburg (SXM)
9.2/10 Wonderful! (1,309 reviews)
*Modern clean rooms. *Having a few dishes, microwave, mini-fridge turned out to be handy. *Staff was very friendly. *Breakfast buffet was excellent. *Onsite restaurants and many nearby was nice. *Broad selection at the Replay Restaurant & Bar. It was the only one we ate at twice.

Reviewed on Feb 21, 2026

Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Point Blanche
Price was CA $3,447, price is now CA $2,067 per person
CA $2,067
per person
Apr 30 - May 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
10/10 Exceptional! (1 review)
Clean room and the view

Reviewed on Feb 26, 2026

Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Price was CA $2,300, price is now CA $1,441 per person
CA $1,441
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Philipsburg (SXM)
8.6/10 Excellent! (952 reviews)
yes very clean rooms and perfectly mannered staff

Reviewed on Feb 25, 2026

Middle Region Hotel Deals

Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
1 Rhine Road Lowlands
The price is CA $760 per night from Mar 4 to Mar 5
CA $760
CA $923 total
Mar 4 - Mar 5
includes taxes & fees
8/10 Very Good! (2,891 reviews)
Excellent location, friendly staff, wonderful food, very clean.

Reviewed on Feb 25, 2026

Sonesta Maho Beach All Inclusive Resort Casino & Spa
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
2 Beacon Hill Road Simpson Bay
The price is CA $596 per night from Mar 1 to Mar 2
CA $596
CA $730 total
Mar 1 - Mar 2
includes taxes & fees
9/10 Wonderful! (1,999 reviews)
The bathroom and shower was covered with mold.

Reviewed on Feb 25, 2026

The Morgan Resort Spa Village
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Billy Folly Road 37 Simpson Bay
The price is CA $360 per night from Mar 3 to Mar 4
CA $360
CA $445 total
Mar 3 - Mar 4
includes taxes & fees
9/10 Wonderful! (1,611 reviews)
Very courteous

Reviewed on Feb 25, 2026

Simpson Bay Resort, Marina & Spa
See all 3,499 properties in Middle Region
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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Beach Vacations
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Frequently asked questions

How much does a Middle Region vacation package cost?
From as low as CA $1,240. Yes, you read that correctly. Our Middle Region packages are a simple way to make your dollar go further. Bundle your favorite hotels, flights and car rentals and get out and explore this top destination.
How do I get a cheap travel package to Middle Region?
Bundle your flights and hotels with Expedia to save on your next exciting adventure. With over 550 partner airlines and 1,000,000 hotel options worldwide, your Middle Region vacation package can be tailored exactly to suit your budget. With all that extra money, why not include a few exciting tours and experiences? It's an easy way to unlock even more bargains. That vacation you've always dreamed of in Middle Region is much closer than you thought!
How far in advance should I book my Middle Region vacation?
Savvy travelers often reserve their seats as early as possible. You can usually start comparing international airfares on Expedia up to 12 months before your flight. If you're purchasing tickets last minute, there's no need to worry. Low prices occasionally occur just weeks before departure dates.
What does an Expedia Middle Region travel package include?
It comes down to what you want. If you're traveling alone, you might decide to bundle hotels and flights. Bringing the whole family to Middle Region? A travel package including flights, hotels and rental cars might be a better fit. Expedia gives you the flexibility and freedom to tailor your travel package.
What should I know before booking a Middle Region travel package?
Bundling your bookings into a Middle Region vacation package is the most convenient way to organize your trip. Not only that, you'll get great discounts when you combine your hotels, flights and car rentals. Once you've booked, why not add on an activity or a tour?
Can I choose my airline with a Middle Region Expedia vacation package?
Yes, and with more than 550 airlines to select from around the world, you have plenty of choice. Look through the available options and find out which airline best suits your budget and needs.
If I'm not able to travel, can I cancel my Middle Region vacation package?
You can. We totally understand that life happens, so we're happy to help if you have to make changes to your Middle Region vacation package. You may be able to cancel or change your itinerary for free if you've booked in the last 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Look up our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.