Vineyard Vacations from $623

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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

$623

per person

Dec 7 - Dec 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9.2/10 Wonderful! (1,000 reviews)

The Villas at Simpson Bay Resort

Pelican Key

$858

per person

Nov 12 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9.2/10 Wonderful! (1,549 reviews)

Simpson Bay Resort, Marina & Spa

Pelican Key

$1,400

per person

Dec 13 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9/10 Wonderful! (2,057 reviews)

The Morgan Resort Spa Village

Save 100% on your flight

$877

per person

Dec 7 - Dec 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9/10 Wonderful! (2,409 reviews)

The resort was amazing!! The staff was very friendly and helpful. The front desk staff Shavonne and concierge were helpful in planning activities to do on the island. Carlos, the doorman was amazing and friendly. Gabby and Nick were great bartenders. The room was clean.

Reviewed on Sep 27, 2026

Panorama Residences at Monte Vista

Point Blanche

Save 100% on your flight

$787

per person

Dec 7 - Dec 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9.6/10 Exceptional! (93 reviews)

I a wonderful stay! The place was clean, comfortable, and exactly as described. The location was convenient, and everything we needed was provided. The host was friendly, responsive, and made the whole experience easy and enjoyable. We really appreciated the attention to detail and would definitely stay here again. Highly recommend!

Reviewed on Sep 23, 2026

Where to stay in Vineyard

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

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 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 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.

Hope Estate

While Hope Estate might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Front Street District and Guana Bay Beach.

Vineyard Hotel Deals

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37 Simpson Bay

Fully refundableReserve now, pay when you stay

$183 nightly

$191 total

Oct 12 - Oct 13

Total with taxes and fees

Sonesta Maho Beach All Inclusive Resort Casino & Spa

1 Rhine Road Lowlands

$346 nightly

$398 total

Oct 20 - Oct 21

Total with taxes and fees

8/10 Very Good! (3,234 reviews)

"The establishment was nice. Was a little sad they advertise an additional restaurant that they dont currently have. Other than that everything was good."

Reviewed on Sep 28, 2026

The Morgan Resort Spa Village

2 Beacon Hill Road Simpson Bay

Fully refundableReserve now, pay when you stay

$449 nightly

$471 total

Oct 28 - Oct 29

Total with taxes and fees

9/10 Wonderful! (2,409 reviews)

"The resort was amazing!! The staff was very friendly and helpful. The front desk staff Shavonne and concierge were helpful in planning activities to do on the island. Carlos, the doorman was amazing and friendly. Gabby and Nick were great bartenders. The room was clean."

Reviewed on Sep 27, 2026

See all 3,594 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.