Vineyard Vacations from $764
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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.
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Save 100% on your flight
Price was $1,227, price is now $764 per person
$764
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (973 reviews)
I had an amazing stay. Peaceful Quite and beautiful the staff was amazing. Breakfast delivery every morning. If I had any questions or needed help they answered and helped me right away. I will definitely stay again.
Reviewed on Dec 18, 2025
Simpson Bay Resort, Marina & Spa
Pelican Key
Price was $2,797, price is now $1,252 per person
$1,252
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (1,463 reviews)
Older hotel and ammenities. Well kept and overall great staff.
Reviewed on Dec 23, 2025
The Villas at Simpson Bay Resort
Price was $4,085, price is now $1,893 per person
$1,893
per person
Feb 8 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,309 reviews)
Great accommodations and ocean view from the balcony. Close to great restaurants and bars. Overall a wonderful vacation.
Reviewed on Dec 20, 2025
Divi Little Bay Beach Resort
Save 100% on your flight
Price was $1,805, price is now $1,153 per person
$1,153
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
8.4/10 Very Good! (1,002 reviews)
We paid more to book a beachfront room. We did not receive beachfront rooms due to remodeling. We were not informed prior to arrival that there would be a change nor did we get any compensation for the change. The manager we spoke with was unconcerned about the change and made us feel like we should be glad we got a room with a view. The facility and other staff were nice. Food options were good. This review would have been 5 stars if we had received the room we booked or a refund in the difference of price.
Reviewed on Dec 21, 2025
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 Sint Maarten Park and Great Bay Beach.
Vineyard Hotel Deals
The Morgan Resort Spa Village
2 Beacon Hill Road Simpson Bay
Fully refundableReserve now, pay when you stay
$394 nightly
The price is $411 total per night from Jan 11 to Jan 12
$411 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
8.8/10 Excellent! (1,906 reviews)
Beautiful hotel. Very clean and modern. Food very pricey and just ok.
Reviewed on Dec 18, 2025
Sonesta Maho Beach All Inclusive Resort Casino & Spa
1 Rhine Road Lowlands
$500 nightly
The price is $522 total per night from Dec 24 to Dec 25
$522 total
Dec 24 - Dec 25
Total with taxes and fees
7.8/10 Good! (2,787 reviews)
Excellent
Reviewed on Dec 20, 2025
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
$338 nightly
The price is $352 total per night from Jan 7 to Jan 8
$352 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
8.8/10 Excellent! (1,535 reviews)
The room was spotless clean smelling good ,and beautiful. The staff were nice. I loke that they had room service. I will definitely come back.
Reviewed on Dec 18, 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.
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
Edge Ferry Tickets to St. Barts
$100
per adult
84% of travellers recommend
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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
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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.