Middle Region Vacation Packages

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Top Holiday Package Deals in Middle Region

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was CA $3,011, price is now CA $1,475 per person
CA $1,475
per person
Jun 22 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.8/10 Excellent! (1,635 reviews)
Perfect room with beach view and all necessary amenities on property. We will come back.

Reviewed on Apr 13, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was CA $3,425, price is now CA $1,613 per person
CA $1,613
per person
Jun 22 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,382 reviews)
Pool, Beach , restaurants , shops , coffee / snack bar , what’s there not to love! We used the very nice gym daily although an extra charge of 5/6$ per visit . Bartender at the main pool bar was fabulous ! Rolls weee comfortable , my boys loved the Murphy beds . Market close by , can walk to all the restaurants . Booked a second floor villa and it was perfect ! Loved this resort for our family spring break !

Reviewed on Apr 5, 2026

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was CA $2,812, price is now CA $1,619 per person
CA $1,619
per person
Jun 22 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,002 reviews)
Welcoming staff was wonderful

Reviewed on Apr 12, 2026

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was CA $2,533, price is now CA $1,657 per person
CA $1,657
per person
Jun 22 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (2,052 reviews)
we enjoyed our stay at the morgan. the staff was friendly and accommodating. anytime we needed a taxi, they would arrange for one within a few minutes. the pool side service was good, we enjoyed our veg impossible burgers and the bbq chicken. the drinks at the bar were consistently good. loved the espresso martinis. on our last day getting onto the airport shuttle, getting help with our luggages was much appreciated. i was apprehensive after i read a few negative reviews prior to coming here but it was a great time. we stayed in a 2 queen ocean view room with nice views. had a nice vacation with family =)

Reviewed on Apr 12, 2026

Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Point Blanche
Price was CA $2,318, price is now CA $1,535 per person
CA $1,535
per person
Jun 19 - Jun 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.6/10 Exceptional! (42 reviews)
The only improvement we would recommend is softer pillows. The pillows we had seemed like staging pillows and not comfortable.

Reviewed on Apr 7, 2026

Middle Region Hotel Deals

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
2 Beacon Hill Road Simpson Bay
Fully refundableReserve now, pay when you stay
The price is CA $382 per night from May 10 to May 11
CA $382
CA $490 total
May 10 - May 11
includes taxes & fees
9/10 Wonderful! (2,072 reviews)
we enjoyed our stay at the morgan. the staff was friendly and accommodating. anytime we needed a taxi, they would arrange for one within a few minutes. the pool side service was good, we enjoyed our veg impossible burgers and the bbq chicken. the drinks at the bar were consistently good. loved the ...

Reviewed on Apr 12, 2026

The Morgan Resort Spa Village
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 $509 per night from Apr 27 to Apr 28
CA $509
CA $616 total
Apr 27 - Apr 28
includes taxes & fees
8/10 Very Good! (2,930 reviews)
Staff is very friendly and accommodating to your needs. We had some issues with the cleaning of our bathroom even after leaving a generous tip on the first day of our stay. Ashanti at reception was very nice and took care of our issues. The breakfast food was ok the lunch and dinner food at the buffet ...

Reviewed on Apr 12, 2026

Sonesta Maho Beach All Inclusive Resort Casino & Spa
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Billy Folly Road 37 Simpson Bay
The price is CA $299 per night from May 14 to May 15
CA $299
CA $365 total
May 14 - May 15
includes taxes & fees
8.8/10 Excellent! (1,658 reviews)
Perfect room with beach view and all necessary amenities on property. We will come back.

Reviewed on Apr 13, 2026

Simpson Bay Resort, Marina & Spa
See all 3,546 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.
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Frequently asked questions

How much does a Middle Region vacation package cost?
From as low as CA $1,475. 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.