Vineyard Vacation Packages

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Top Holiday Package Deals in Vineyard

Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was CA $2,671, price is now CA $1,522 per person
CA $1,522
per person
May 4 - May 11
found 22 hours ago
Roundtrip non-stop flight included
Montreal Metropolitan Airport (YHU) to Philipsburg (SXM)
9.2/10 Wonderful! (1,007 reviews)
Very accommodating staff, beautiful area. A little bit of a trek down to the water but the trade off was an amazing view from our balcony.

Reviewed on Mar 13, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was CA $3,314, price is now CA $1,523 per person
CA $1,523
per person
May 24 - May 29
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,629 reviews)
Room was perfectly situated, good exercise walking up the hill. Never disappoints!

Reviewed on Mar 16, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was CA $3,443, price is now CA $1,618 per person
CA $1,618
per person
May 4 - May 11
found 22 hours ago
Roundtrip non-stop flight included
Montreal Metropolitan Airport (YHU) to Philipsburg (SXM)
9.2/10 Wonderful! (1,387 reviews)
Resort was clean and transportation was readily accessible

Reviewed on Mar 17, 2026

Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Point Blanche
Price was CA $2,867, price is now CA $1,799 per person
CA $1,799
per person
May 23 - May 30
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.6/10 Exceptional! (29 reviews)
Amazing property. This one is pretty new. At the time of our stay, the concierge (Nicky) said it had only been open for about 3 months. Nicky was amazing, always one message away and extremely helpful with planning. Did not get to use the pool but it looked beautiful, and it is open 24/7. The views are amazing. I would definitely stay here again, though, you should be wary that it is pretty high up in a hill. The traffic was pretty bad to the other areas but it may have been the time that we visited, which was peak season. I wish the water in the shower was a little more hot. Otherwise, amazing stay, amazing property! Will definitely book again.

Reviewed on Mar 13, 2026

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was CA $3,263, price is now CA $2,105 per person
CA $2,105
per person
May 4 - May 11
found 22 hours ago
Roundtrip non-stop flight included
Montreal Metropolitan Airport (YHU) to Philipsburg (SXM)
9/10 Wonderful! (2,033 reviews)
The people were friendly and nice, the grounds well kept and clean. The rooms were large, clean and comfortable. Stayed twice in six weeks for work and enjoyed both stays.

Reviewed on Mar 18, 2026

Where to stay in Vineyard

Find the best Vineyard areas and neighborhoods for the activities you enjoy most. Learn more about Vineyard
Philipsburg St Maarten panoramic cityscape.

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.

Find hotels in Downtown Philipsburg

Vineyard Hotel Deals

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
2 Beacon Hill Road Simpson Bay
Fully refundableReserve now, pay when you stay
The price is CA $570 per night from Apr 1 to Apr 2
CA $570
CA $700 total
Apr 1 - Apr 2
includes taxes & fees
9/10 Wonderful! (2,029 reviews)
The people were friendly and nice, the grounds well kept and clean. The rooms were large, clean and comfortable. Stayed twice in six weeks for work and enjoyed both stays.

Reviewed on Mar 18, 2026

The Morgan Resort Spa Village
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
1 Rhine Road Lowlands
The price is CA $554 per night from Apr 6 to Apr 7
CA $554
CA $670 total
Apr 6 - Apr 7
includes taxes & fees
8/10 Very Good! (2,898 reviews)
My Sonesta Maho vacation was amazing! From the check-in to the actual 6 night stay to the check-out, no issues or complaints. Our room was cleaned daily, the food was good, the gym was sufficient for my use and I had a great time using the pool daily. The entire staff was friendly and helpful. I ...

Reviewed on Mar 18, 2026

Sonesta Maho Beach All Inclusive Resort Casino & Spa
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Billy Folly Road 37 Simpson Bay
The price is CA $426 per night from Apr 15 to Apr 16
CA $426
CA $521 total
Apr 15 - Apr 16
includes taxes & fees
8.8/10 Excellent! (1,627 reviews)
No complaints

Reviewed on Mar 17, 2026

Simpson Bay Resort, Marina & Spa
See all 3,534 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.
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Frequently asked questions

How much does a Vineyard vacation package cost?
Get set to book, because a trip to Vineyard starts from an enticing CA $1,522. When you bundle your flights, hotels and more into a package, you'll pick up the biggest deals.
How do I get a cheap travel package to Vineyard?
Crafting your own Vineyard vacation package with Expedia is such a simple way to save. We have over 550 partner airlines and 1,000,000 hotel options across the globe. With such an amazing range to pick from, you'll have no issues pulling together your perfect adventure.
Where should I stay in Vineyard?
If you plan to visit Guana Bay Beach, maximize your time sightseeing and book a hotel room nearby. It's one of the top attractions in this area.
What are the top hotels in Vineyard?
When it comes to comfy and convenient places to stay in Vineyard, you can't go past Apartment With 4 Bedrooms In Philipsburg. Take a look at its deals and pick up a great price.
How far in advance should I book my Vineyard vacation?
Browse Expedia to compare international flights ASAP. In many cases, you can purchase a seat up to a year before departure. If you don't see your preferred carrier, or you're booking late, don't despair. The lowest prices to Vineyard sometimes occur a few weeks before departure.
What does an Expedia Vineyard travel package include?
That depends on what kind of getaway you're thinking about. Vineyard vacation deals can include hotels, car rentals and flights. You can mix and match to find the travel package that suits you. You can also add on activities and experiences after you've booked to get even bigger discounts.
What should I know before booking a Vineyard travel package?
You'll score terrific savings when you bundle your hotels, flights and rental cars into a travel package. Plus, booking everything together just makes things easier. So why waste time or money? Whether you're organizing a ritzy city getaway or a low-cost family break, take a look at our vacation packages today.
Can I choose my airline with a Vineyard Expedia vacation package?
You certainly can. Expedia has access to more than 550 airline partners around the world, so pick the carrier that's a good fit for your budget needs.
If I'm not able to travel, can I cancel my Vineyard vacation package?
If your vacation plans in Vineyard have been upended, it's comforting to know that you can amend or cancel your booking. If your booking was made less than 24 hours ago, you may be eligible to receive a refund. If your booking is older than that, your hotel, airline or car rental company may impose fees. To find out more, check our Customer Service Portal.

Discover the most popular places to visit in Vineyard

Great Bay Beach showing general coastal views, a sandy beach and a coastal town

Great Bay Beach

4/5(20 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.

Great Bay Beach
Fort Amsterdam which includes château or palace, a ruin and military items

Fort Amsterdam

5/5(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.

Fort Amsterdam
Museum of Sint Maarten which includes art and interior views

Museum of Sint Maarten

Discover where the native population originally came from and learn about major events in the island’s colonial, social and natural past.

Museum of Sint Maarten

Things to do

Panoramic view of vibrant St. Martin

Edge Ferry Tickets to St. Barts

CA $137
per adult
84% of travellers recommend
Edge Ferry Tickets to St. Barts
Sand Dollar Snorkeling Adventure

Half Day Snorkeling Adventure

CA $89
per adult
100% of travellers recommend
Half Day Snorkeling Adventure
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

CA $218
per adult
90% of travellers recommend
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
See all activities in Philipsburg
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.