Vineyard Vacations from $824
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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.
Oyster Bay Beach Resort
Oyster Pond
Save 100% on your flight
Price was $1,465, price is now $824 per person
$824
per person
Apr 13 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
8.6/10 Excellent! (952 reviews)
Great stay. Good property and good restaurants choices.
Reviewed on Feb 5, 2026
The Villas at Simpson Bay Resort
Pelican Key
Price was $2,750, price is now $1,279 per person
$1,279
per person
Apr 13 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,309 reviews)
It was our 2nd time there. It was great. We love being able to walk to restaurants and live music. Staff is always friendly and funny!
Reviewed on Feb 6, 2026
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Price was $1,799, price is now $873 per person
$873
per person
Apr 13 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (973 reviews)
Room was very clean and staff was friendly. The room was spacious and elegant and had a great view.
Reviewed on Feb 5, 2026
Simpson Bay Resort, Marina & Spa
Pelican Key
Save 100% on your flight
Price was $1,623, price is now $850 per person
$850
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (1,463 reviews)
Room was spacious and spotless. Staff was friendly and helpful. The pools were perfect!
Reviewed on Feb 6, 2026
Panorama Residences at Monte Vista
Point Blanche
Save 100% on your flight
Price was $2,005, price is now $1,158 per person
$1,158
per person
Apr 13 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
10/10 Exceptional! (1 review)
We had such a wonderful stay! The apartment was spotless, stylish, and felt like home. Nicky and Edsel went above and beyond as concierge. so helpful, kind, and generous throughout our trip. Truly made the experience special. Highly recommend staying here!
Reviewed on Feb 4, 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
$479 nightly
The price is $500 total per night from Feb 15 to Feb 16
$500 total
Feb 15 - Feb 16
Total with taxes and fees
8.8/10 Excellent! (1,988 reviews)
Nice rooms. Friendly staff. Great food. Wonderful pool. Great restaurants near by. Would definitely come again.
Reviewed on Feb 3, 2026
Sonesta Maho Beach All Inclusive Resort Casino & Spa
1 Rhine Road Lowlands
$657 nightly
The price is $685 total per night from Feb 9 to Feb 10
$685 total
Feb 9 - Feb 10
Total with taxes and fees
7.8/10 Good! (2,864 reviews)
Amazing Location, Excellent food, and clean room. Staff was ok ok in compare to overall other experiences in Caribbean.
Reviewed on Feb 4, 2026
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
$381 nightly
The price is $398 total per night from Mar 7 to Mar 8
$398 total
Mar 7 - Mar 8
Total with taxes and fees
8.8/10 Excellent! (1,592 reviews)
The staff were extremely helpful and attentive everywhere across the resort. From the front desk staff to the bartenders (especially Sofia at the beach bar) and everyone in between. We will definitely be coming back for a MUCH longer stay!
Reviewed on Feb 4, 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
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
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
$135
per adult
90% of travellers recommend
Edge Ferry Tickets to St. Barts
$100
per adult
84% of travellers recommend
Explore a world of travel with Expedia
- Hotels near University of St. Martin
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- Museum of Sint Maarten
- Cyrus Wathey Square
- Philipsburg Courthouse
- 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
- Car rentals near University of St. Martin
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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.