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
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,254 reviews)
The staff were friendly. Check in was quick and smooth and the wait time for our room was minimal. I especially loved that there was house keeping every day.

Reviewed on Aug. 3, 2025

La Playa Orient Bay

La Playa Orient Bay

4 out of 5
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9.4/10 Exceptional! (577 reviews)
We loved everything about the property. 10 out of 10 The staff was amazing from front desk to house keeping and dining! Would definitely go back again.

Reviewed on Aug. 4, 2025

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,218 reviews)
Lovely had a great time

Reviewed on Aug. 4, 2025

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (946 reviews)
Wonderful customer service

Reviewed on Aug. 3, 2025

Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.6/10 Excellent! (906 reviews)
Needs more food options, and updates to the property.

Reviewed on Aug. 3, 2025

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, Maho Bay, Lowlands
The price is CA $323 per night from Aug 18 to Aug 19
CA $323
CA $390 total
Aug 18 - Aug 19
includes taxes & fees
7.8/10 Good! (2,452 reviews)
"Just beautiful"

Reviewed on Aug. 3, 2025

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
Fully refundableReserve now, pay when you stay
The price is CA $284 per night from Aug 10 to Aug 11
CA $284
CA $380 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (1,790 reviews)
"Convenient, but crowded area, great for young adults"

Reviewed on Aug. 2, 2025

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 $90 per night from Aug 18 to Aug 19
CA $90
CA $109 total
Aug 18 - Aug 19
includes taxes & fees
8.8/10 Excellent! (1,263 reviews)
"Beautiful location, rooms are spacious and food was AMAZING!"

Reviewed on Jul. 31, 2025

Simpson Bay Resort, Marina & Spa
See all 3,577 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
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
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Frequently asked questions

How much does a Middle Region vacation package cost?
From as low as CA $1,059. 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.