Vineyard Vacations from $867
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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 $2,873, price is now $1,333 per person
$1,333
per person
Apr 28 - May 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,387 reviews)
Nice room. Great view. Staff could be a bit friendlier overall - at the bar, beach staff putting out chairs, etc. overall nice stay
Reviewed on Mar 22, 2026
The Morgan Resort Spa Village
Save 100% on your flight
Price was $2,419, price is now $1,476 per person
$1,476
per person
Apr 28 - May 5
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (2,033 reviews)
We had a great stay on this incredible property. A few things that stood out were the kind staff, ideal location, and amazing facility.
Reviewed on Mar 24, 2026
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Save 100% on your flight
Price was $1,636, price is now $1,001 per person
$1,001
per person
Apr 28 - May 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,007 reviews)
We have had another wonderful stay at Princess Heights Luxury Hotel. We were there for 12 days and we love the location. We had the ocean view to wake up to every morning which was amazing and lovely to sit on the patio to wake up slowly.
Very quiet location, attentive staff, good restaurants within driving distance. Dawn Beach is close to walk to but small.
We were lucky to see some monkeys while there also.
We highly recommend this location, however, you do need a car or use a taxi to get around.
The pool was lovely and such a great way to relax at the end of a busy day of sightseeing.
Reviewed on Mar 26, 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
3 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 Museum of Sint Maarten.
Vineyard Hotel Deals
The Morgan Resort Spa Village
2 Beacon Hill Road Simpson Bay
Fully refundableReserve now, pay when you stay
$490 nightly
The price is $511 total per night from Apr 9 to Apr 10
$511 total
Apr 9 - Apr 10
Total with taxes and fees
9/10 Wonderful! (2,043 reviews)
We had a great stay on this incredible property. A few things that stood out were the kind staff, ideal location, and amazing facility.
Reviewed on Mar 24, 2026
Sonesta Maho Beach All Inclusive Resort Casino & Spa
1 Rhine Road Lowlands
$427 nightly
The price is $445 total per night from Apr 20 to Apr 21
$445 total
Apr 20 - Apr 21
Total with taxes and fees
8/10 Very Good! (2,897 reviews)
We loved our stay.
Reviewed on Mar 26, 2026
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
$280 nightly
The price is $294 total per night from Apr 20 to Apr 21
$294 total
Apr 20 - Apr 21
Total with taxes and fees
8.8/10 Excellent! (1,631 reviews)
We were on the 5th floor on top of the hill dacing ocean. The view is breath taking. It was an amazing place. We can’t wait go back!!
Reviewed on Mar 26, 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.
Discover the most popular places to visit in Vineyard
Great Bay Beach
4.5/5(90 reviews)
If a restful vacation is part of your travel plans, Great Bay Beach might be the perfect place to seek out during your trip to Philipsburg. Check out the shops and top-notch restaurants in this romantic area.
Philipsburg Boardwalk
Philipsburg Boardwalk is just one of the places to see in Philipsburg, so why not enjoy the other things to explore during your travels? Stroll along the area's beaches or simply enjoy its restaurants.
Fort Amsterdam
2/5(2 reviews)
The remains of the first Dutch military base in the Caribbean offer stunning views across the ocean and over the town of Philipsburg behind it.
Things to do
Sint Maarten: World's First Caribbean Carnival Experience
$40
per adult
100% of travellers recommend
Edge Ferry Tickets to St. Barts
$100
per adult
84% of travellers recommend
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- Museum of Sint Maarten
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- Philipsburg Vacations
- Visit Philipsburg
- Sint Maarten Park
- Visit Upper Prince's Quarter
- Great Bay Beach
- Visit Sucker Garden
- Guana Bay Beach
- Sint Maarten Vacations
- Fort Amsterdam
- Little Bay Beach
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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.