Vineyard Vacations from $698
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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 $1,318, price is now $795 per person
$795
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (966 reviews)
The room was clean and very comfortable and the decor was simple and modern. The staff was excellent. We were brought to our room and shown the compounds by the front office. The oceanview was absolutely breathtaking and breakfast being brought to us every morning to enjoy on the balcony was another unexpected treat! I would definitely stay here again if I ever get the chance to return to St. Maarten!
Reviewed on Nov 3, 2025
Oceans at Divi Little Bay
Save 100% on your flight
Price was $1,936, price is now $1,239 per person
$1,239
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
8.4/10 Very Good! (262 reviews)
The balcony had a ocean view that was very relaxing. The room was clean and the staff was professional and accommodating.
Reviewed on Oct 23, 2025
Divi Little Bay Beach Resort
Save 100% on your flight
Price was $1,830, price is now $1,186 per person
$1,186
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
8.4/10 Very Good! (1,001 reviews)
The facility and the rooms were great and very well kept up with. However, the food was terrible.
Reviewed on Oct 31, 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
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 Sint Maarten Park.
Vineyard Hotel Deals
Sonesta Maho Beach All Inclusive Resort Casino & Spa
1 Rhine Road, Maho Bay, Lowlands
$362 nightly
The price is $378 total per night from Nov 12 to Nov 13
$378 total
Nov 12 - Nov 13
Total with taxes and fees
7.8/10 Good! (2,710 reviews)
Staff was awesome, especially Angela thank you very much for your service.
Reviewed on Nov 3, 2025
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37, Simpson Bay
Fully refundableReserve now, pay when you stay
$154 nightly
The price is $160 total per night from Nov 24 to Nov 25
$160 total
Nov 24 - Nov 25
Total with taxes and fees
8.8/10 Excellent! (1,438 reviews)
Great location excellent Service
Reviewed on Nov 2, 2025
The Morgan Resort Spa Village
2 Beacon Hill Road, Simpson Bay
Fully refundable
$340 nightly
The price is $354 total per night from Nov 18 to Nov 19
$354 total
Nov 18 - Nov 19
Total with taxes and fees
8.8/10 Excellent! (1,858 reviews)
Very nuce
Reviewed on Oct 31, 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
4.5/5(88 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
Edge Ferry Tickets to St. Barts
$100
per adult
84% of travellers recommend
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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.