Middle Region Vacations from $663
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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
Oyster Pond
Save 100% on your flight
Price was $1,097, price is now $663 per person
$663
per person
Nov 9 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (960 reviews)
Its a beautiful property and the customer service experience is wonderful
Reviewed on Aug 30, 2025
Simpson Bay Resort, Marina & Spa
Pelican Key
Save 100% on your flight
Price was $1,636, price is now $808 per person
$808
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (1,291 reviews)
The property is beautiful, service reps were great. Food on the resort was delicious, excursions provided were very nice. It was affordable, but you do get what you pay for. I chose the least expensive room, and it was very nice, but the furthest away from everything, except its own pool, so lots of walking in the heat. The toilet and sink leaked. I called twice and no one came and it was never fixed. I ended up putting towels on the floor behind the toilet and next to the sink to absorb the water. We were leaving 2 1/2 days later, so I didn’t pursue it. Hopefully it’s fixed for the next customer. If I ever go back to St Martin, I would stay again in a different section of the resort.
Reviewed on Sep 2, 2025
The Villas at Simpson Bay Resort
Save 100% on your flight
Price was $1,603, price is now $882 per person
$882
per person
Nov 9 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,227 reviews)
No welcome drinks when we arrived. Limited excursions on certain days.
Reviewed on Sep 2, 2025
Holland House Beach Hotel
Downtown Philipsburg
Save 100% on your flight
Price was $2,384, price is now $1,454 per person
$1,454
per person
Nov 9 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,003 reviews)
Wonderful stay. Only issue is the WiFi for the TV wasn’t stable but all else was amazing!
Reviewed on Aug 27, 2025
Hilton Vacation Club Royal Palm St. Maarten
Save 100% on your flight
Price was $1,088, price is now $664 per person
$664
per person
Nov 9 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (1,084 reviews)
Bar staff was the best from Morgan and her team.
Reviewed on Sep 2, 2025
Middle Region Hotel Deals
Sonesta Maho Beach All Inclusive Resort Casino & Spa
1 Rhine Road, Maho Bay, Lowlands
$241 nightly
The price is $252 total per night from Sep 3 to Sep 4
$252 total
Sep 3 - Sep 4
Total with taxes and fees
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37, Simpson Bay
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $99 total per night from Sep 4 to Sep 5
$99 total
Sep 4 - Sep 5
Total with taxes and fees
8.8/10 Excellent! (1,289 reviews)
"Loved It"
Reviewed on Aug 31, 2025
The Morgan Resort Spa Village
2 Beacon Hill Road, Simpson Bay
$278 nightly
The price is $289 total per night from Sep 7 to Sep 8
$289 total
Sep 7 - Sep 8
Total with taxes and fees
8.8/10 Excellent! (1,830 reviews)
"Amazing - make sure to check out the observation deck!"
Reviewed on Sep 1, 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.