Vineyard Vacations from $1,093
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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.
Simpson Bay Resort, Marina & Spa
Pelican Key
Price was $2,482, price is now $1,093 per person
$1,093
per person
Jun 13 - Jun 20
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Philipsburg (SXM)
9/10 Wonderful! (1,695 reviews)
Perfect place to stay. 100% recommended. It got pool, beach, restaurants, shuttles within the resort area.
Reviewed on May 13, 2026
The Villas at Simpson Bay Resort
Pelican Key
Save 100% on your flight
Price was $2,916, price is now $1,411 per person
$1,411
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philipsburg (SXM)
9.2/10 Wonderful! (1,383 reviews)
Not available, we had only a kitchenette
Reviewed on May 13, 2026
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Price was $1,775, price is now $1,250 per person
$1,250
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philipsburg (SXM)
9.2/10 Wonderful! (1,002 reviews)
Suzanna and Hattie front desk ladies were fantastic! They helped me out so much! The driver was wonderful all the staff were so friendly! Love them. I will say if you’re not ready to walk up & down stairs, or don’t have a rental car, it was a little tough. Other than that no issues here friends and I enjoyed ourselves.
Reviewed on May 12, 2026
La Playa Orient Bay
Price was $2,148, price is now $1,541 per person
$1,541
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philipsburg (SXM)
9.4/10 Exceptional! (701 reviews)
The breakfast has so many delicious options! It’s not your usual continental breakfast. They go above and beyond. The staff are all friendly and very accommodating. We have stayed there 3 times and always look forward to seeing the staff. They must be doing something right to keep the staff. Love having the chairs and umbrellas. Would definitely recommend.
Reviewed on May 10, 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 Front Street District.
Vineyard Hotel Deals
The Morgan Resort Spa Village
2 Beacon Hill Road Simpson Bay
Fully refundableReserve now, pay when you stay
$370 nightly
The price is $385 total per night from Jun 7 to Jun 8
$385 total
Jun 7 - Jun 8
Total with taxes and fees
9/10 Wonderful! (2,133 reviews)
Was so good in February, I had to come back for carnival!!! Many food choices and a grocery store in waking distance. The staff are helpful and friendly so check your own energy first to keep the vibes up. Speaking of vibes, the pool vibes are just what you're looking for; aestetically awesome, food ...
Reviewed on May 12, 2026
Sonesta Maho Beach All Inclusive Resort Casino & Spa
1 Rhine Road Lowlands
$391 nightly
The price is $407 total per night from May 19 to May 20
$407 total
May 19 - May 20
Total with taxes and fees
8/10 Very Good! (2,965 reviews)
Very clean, staff is friendly and helpful. Food was good. Only thing I didn’t care for were the kids next to use moving furniture and running and screaming at 5:30 in the morning.
Reviewed on May 12, 2026
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
Fully refundableReserve now, pay when you stay
$244 nightly
The price is $256 total per night from May 14 to May 15
$256 total
May 14 - May 15
Total with taxes and fees
9/10 Wonderful! (1,722 reviews)
Perfect place to stay. 100% recommended. It got pool, beach, restaurants, shuttles within the resort area.
Reviewed on May 13, 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
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
$159
per adult
90% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
$85
per adult
94% of travellers recommend
Explore a world of travel with Expedia
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- Museum of Sint Maarten
- Cyrus Wathey Square
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- Yoda Guy Movie Exhibit
- 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
- All inclusive Vacation Packages Sint Maarten
- Visit Sint Maarten
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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.