Vineyard Vacations from $650

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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

$650

per person

Sep 14 - Sep 18

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Philipsburg (SXM)

9.2/10 Wonderful! (1,003 reviews)

This property is nice.. it almost felt deserted as we didn’t see anyone at night. It was very clean, comfortable and we had everything needed. My only complaint was the room needed more light. I’d stay here again .

Reviewed on Aug 8, 2026

The Villas at Simpson Bay Resort

Pelican Key

$828

per person

Oct 13 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Philipsburg (SXM)

9.2/10 Wonderful! (1,484 reviews)

Seul bémol pour moi est le bruit occasionné le soir par les Bar aux alentour de la baie. il ne vaut pas être un couche tôt. La vue est belle face aux bateaux amarrés, Bon choix de resto aux alentours. Juste à coté du casino pour ceux et celles qui aiment bien alle dépenser un petit 20 le soir.

Reviewed on Aug 13, 2026

Simpson Bay Resort, Marina & Spa

Pelican Key

Save 100% on your flight

$678

per person

Oct 13 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Philipsburg (SXM)

9/10 Wonderful! (1,922 reviews)

La Playa Orient Bay

Save 100% on your flight

$804

per person

Oct 15 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Philipsburg (SXM)

9.4/10 Exceptional! (773 reviews)

The Morgan Resort Spa Village

Save 100% on your flight

$1,146

per person

Oct 13 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Philipsburg (SXM)

9/10 Wonderful! (2,341 reviews)

Where to stay in Vineyard

Find the best Vineyard areas and neighborhoods for the activities you enjoy most. Learn more about Vineyard

A coastal town with buildings, a clear blue sea, and mountains in the background.

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.

A coastal cityscape with a marina, residential buildings, and a mountainous backdrop.

Indigo Bay

While Indigo Bay isn't home to many top sights, Little Bay Beach and Indigo Beach are some notable places to visit nearby.

A large cruise ship docked at a pier with a mountainous coastline and sailboats in the background.

Point Blanche

1 out of top 10 points of interest in this area

While visiting Point Blanche, you might make a stop by sights like Port of St. Maarten and Harbour Point Village.

A coastal town with a marina, mountains, and a bay.

Belair

While Belair isn't home to many top sights, Little Bay Beach and Great Bay Beach are some notable places to visit nearby.

A marina with boats and a mountainous backdrop.

Sucker Garden

Sucker Garden might not have many top sights, but Guana Bay Beach and Dawn Beach are two attractions nearby that you can check out.

Vineyard Hotel Deals

The Morgan Resort Spa Village

2 Beacon Hill Road Simpson Bay

Fully refundableReserve now, pay when you stay

$513 nightly

$539 total

Sep 12 - Sep 13

Total with taxes and fees

Sonesta Maho Beach All Inclusive Resort Casino & Spa

1 Rhine Road Lowlands

$523 nightly

$545 total

Sep 7 - Sep 8

Total with taxes and fees

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37 Simpson Bay

Fully refundableReserve now, pay when you stay

$160 nightly

$168 total

Sep 9 - Sep 10

Total with taxes and fees

See all 3,668 properties in Vineyard

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.