Middle Region Vacations from ￥392,911

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The Latest Middle Region Vacation Packages

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 ￥435,824, price is now ￥392,911 per person
￥392,911
per person
Aug 7 - Aug 10
found 22 hours ago
Roundtrip flight included
Tokyo (TYO) to Philipsburg (SXM)
9.2/10 Wonderful! (1,009 reviews)
The staff and room were excellent. The daily breakfast was wonderful. The BEST croissants anywhere!! It was nice to have the guest laundry; the appliances need to be updated though. The only thing we can think of is a propane bbq(s) would be very much appreciated. Charcoal takes much too long to wait be fire you can cook your meal. Thank you PH for a fantastic stay.

Reviewed on Jun 18, 2026

Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was ￥469,985, price is now ￥425,208 per person
￥425,208
per person
Aug 7 - Aug 10
found 22 hours ago
Roundtrip flight included
Tokyo (TYO) to Philipsburg (SXM)
8.2/10 Very Good! (436 reviews)
Clean and well maintained!

Reviewed on Jun 24, 2026

Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was ￥458,274, price is now ￥416,956 per person
￥416,956
per person
Aug 7 - Aug 10
found 22 hours ago
Roundtrip flight included
Tokyo (TYO) to Philipsburg (SXM)
8.2/10 Very Good! (1,027 reviews)
Property was relaxing and well kept. Everyone very friendly and a great trip

Reviewed on Jun 22, 2026

La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was ￥457,502, price is now ￥416,511 per person
￥416,511
per person
Aug 7 - Aug 10
found 22 hours ago
Roundtrip flight included
Tokyo (TYO) to Philipsburg (SXM)
9.4/10 Exceptional! (733 reviews)
This is a a great hotel - very clean, beautiful beach views and right in the middle of Orient Village. Excellent restaurant and just steps away from your room. And the staff is amazing. They are so kind and helpful. One day we needed a cab for a short ride and a hotel staffer said “it willl take ten minutes for a cab to get here. I will drive you myself.” I can’t say enough good things about the hotel staff.

Reviewed on Jun 22, 2026

Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Point Blanche
Price was ￥473,686, price is now ￥431,663 per person
￥431,663
per person
Aug 7 - Aug 10
found 22 hours ago
Roundtrip flight included
Tokyo (TYO) to Philipsburg (SXM)
9.6/10 Exceptional! (61 reviews)
Great place to stay with an amazing view.

Reviewed on Jun 19, 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 ￥56,846 per night from Jul 13 to Jul 14
￥56,846
￥70,937 total
Jul 13 - Jul 14
includes taxes & fees
9/10 Wonderful! (2,238 reviews)
"I would highly recommend this resort. The property was clean, well-maintained, and the staff was exceptionally friendly and welcoming throughout our stay. While the food on-site was a bit expensive, it was delicious. We chose to dine at local restaurants most evenings and enjoyed exploring the area. ..."

Reviewed on Jun 24, 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 ￥66,074 per night from Jul 13 to Jul 14
￥66,074
￥79,950 total
Jul 13 - Jul 14
includes taxes & fees
8/10 Very Good! (2,985 reviews)
"I like some of the staff were friendly and knowledgeable. I didn’t like that I had to wait an hour for my room to be ready after the check-in time."

Reviewed on Jun 24, 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
Fully refundableReserve now, pay when you stay
The price is ￥38,681 per night from Jul 7 to Jul 8
￥38,681
￥47,573 total
Jul 7 - Jul 8
includes taxes & fees
9/10 Wonderful! (1,816 reviews)
"The villa was amazing and exceeded our expectations! There was so much room for everyone!"

Reviewed on Jun 24, 2026

Simpson Bay Resort, Marina & Spa
See all 3,585 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.

Frequently asked questions

How much does a Middle Region vacation package cost?
From as low as ￥392,911. 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.