Vineyard Vacations from $884
Book a Hotel + Flight or Car together to unlock savings
Your Vineyard Vacation
Our Vineyard vacation packages are a fast and convenient way to organize and book your next escape. Get to know the essence of this unique neighborhood without the stress of planning everything yourself. Not sure what to do and see during your trip to Vineyard? Nearby attractions like Sint Maarten Park, Little Bay Beach and University of St. Martin are great places to start. Don't just dream it — do it! Lock in your ideal Vineyard vacation with Expedia and enjoy traveling your way.
The Latest Vineyard Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Villas at Simpson Bay Resort
Pelican Key
Price was $4,423, price is now $1,820 per person
$1,820
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,584 reviews)
The property is beautiful and well maintained. The staff was friendly. The rooms are nicely kept and very clean. We had cleaning service every day which was greatly appreciated. The only thing I would complaint about is the hard mattress, very difficult to fall asleep a time.
Reviewed on Nov 12, 2026
Where to stay in Vineyard
Find the best Vineyard areas and neighborhoods for the activities you enjoy most. Learn more about Vineyard
Downtown Philipsburg
2 out of top 10 points of interest in this area
While visiting Downtown Philipsburg, you might make a stop by sights like Great Bay Beach and Front Street District.
Vineyard Hotel Deals
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
Fully refundableReserve now, pay when you stay
$223 nightly
The price is $233 total per night from Dec 11 to Dec 12
$233 total
Dec 11 - Dec 12
Total with taxes and fees
The Morgan Resort Spa Village
2 Beacon Hill Road Simpson Bay
Fully refundableReserve now, pay when you stay
$558 nightly
The price is $582 total per night from Nov 15 to Nov 16
$582 total
Nov 15 - Nov 16
Total with taxes and fees
Sonesta Maho Beach All Inclusive Resort Casino & Spa
1 Rhine Road Lowlands
$462 nightly
The price is $482 total per night from Nov 23 to Nov 24
$482 total
Nov 23 - Nov 24
Total with taxes and fees
8/10 Very Good! (3,315 reviews)
"Great location, but overpriced"
Reviewed on Nov 12, 2026
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.
Things to do
Tango Sunset Cruise with Caribbean Dinner & Open Bar
$77
per adult
94% of travellers recommend
ATV/UTV Guided Tour to Maho Beach – Cruise Passengers
$800
per traveler
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.