Middle Region Vacations from $629
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The Latest Middle Region Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa
Pelican Key
Save 100% on your flight
Price was $1,416, price is now $762 per person
$762
per person
Jan 22 - Jan 25
just found
Roundtrip flight included
New York (NYC) to Philipsburg (SXM)
9/10 Wonderful! (1,398 reviews)
Air conditioning was good and the room was clean and spacious.
Reviewed on Nov 5, 2025
Sapphire Beach Club Resort
Maho
Save 100% on your flight
Price was $1,492, price is now $859 per person
$859
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
7/10 Good! (681 reviews)
Great place to stay for the price. Its a little dated. But we there for the beach more than the room. There is no major beach onsite. But a cool small opening to the ocean. I woukd stay again
Reviewed on Nov 7, 2025
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Save 100% on your flight
Price was $1,732, price is now $1,013 per person
$1,013
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (966 reviews)
Amazing wonderful staff, friendly kind and warm very inviting. They answer right away if you have any question and more. I have amazing stay for my Birhday vacation. It’s safe quite and peaceful and very clean. I will return again and is children friendly.
Reviewed on Nov 7, 2025
Middle Region Hotel Deals
Sonesta Maho Beach All Inclusive Resort Casino & Spa
1 Rhine Road, Maho Bay, Lowlands
$362 nightly
The price is $378 total per night from Nov 12 to Nov 13
$378 total
Nov 12 - Nov 13
Total with taxes and fees
7.8/10 Good! (2,710 reviews)
Staff was awesome, especially Angela thank you very much for your service.
Reviewed on Nov 3, 2025
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37, Simpson Bay
Fully refundableReserve now, pay when you stay
$141 nightly
The price is $147 total per night from Nov 23 to Nov 24
$147 total
Nov 23 - Nov 24
Total with taxes and fees
8.8/10 Excellent! (1,438 reviews)
Great location excellent Service
Reviewed on Nov 2, 2025
The Morgan Resort Spa Village
2 Beacon Hill Road, Simpson Bay
Fully refundable
$332 nightly
The price is $345 total per night from Nov 10 to Nov 11
$345 total
Nov 10 - Nov 11
Total with taxes and fees
8.8/10 Excellent! (1,858 reviews)
Very nuce
Reviewed on Oct 31, 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.