Vineyard Vacation Packages
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- Oyster Bay Beach Resort
Aug 12 - Aug 18Oyster Bay Beach Resort + Flight
Oyster Pond5 nights8.8/10 - Excellent (1,016 reviews)"The hotel is fine- it is safe, etc. But it is just 'mid'. If you are looking for absolute luxury, look elsewhere! I think this is a good option for those who don't want to break the bank, the area it is in though isn't great and a drive to get anywhere."Reviewed May 24, 2026Roundtrip • Halifax (YHZ) - Saint Martin (SXM)YHZ - SXM • 2 stops SXM - YHZ • 2 stopsCA $1,517CA $1,090found 1 day agoper traveller - The Villas at Simpson Bay Resort
Aug 12 - Aug 19The Villas at Simpson Bay Resort + Flight
Pelican Key7 nights9.2/10 - Wonderful (1,402 reviews)"Can't beat this place for anything!!!!! Location-10, Amenities-9, Food nearby, less than a five minute walk.... EXCELLANT!!!!! Catch the bus in front of the area airport, and BAM!!!! 12 minutes later you're at Simpson Bay. Everyone was beyond accommodating and extra nice. The views were incredible and the steady breeze off the bay at night is something you see on "Netflix" !!!!!! All around the best value on the island!!!!!"Reviewed May 25, 2026Roundtrip • Toronto (YYZ) - Saint Martin (SXM)YYZ - SXM • 2 stops SXM - YYZ • 2 stopsCA $3,998CA $1,826found 1 day agoper traveller - Simpson Bay Resort, Marina & Spa
Jul 12 - Jul 19Simpson Bay Resort, Marina & Spa + Flight
Pelican Key7 nights9.0/10 - Wonderful (1,751 reviews)"Good location to town but huge property. Be prepared to walk!"Reviewed May 25, 2026Roundtrip • Montreal (YUL) - Saint Martin (SXM)YUL - SXM • 1 stop SXM - YUL • 1 stopCA $3,767CA $1,792found 1 day agoper traveller - La Playa Orient Bay
Aug 8 - Aug 15La Playa Orient Bay + Flight
Orient Bay7 nights9.4/10 - Exceptional (718 reviews)"Breakfast was very good,room was cleaned everyday,not to much noise where room was located. There are a good amount of restaurants close by for eating out. Beach chairs and beach was maintained good,only problem which has been posted sea weed has to be removed everyday. Transportation to and from airport was handled good by Expedia with vendor provided. The not so good and this goes to Expedia,do not offer room upgrades at Hotels that are not likely to fill the request for frequent Expedia..."Reviewed May 24, 2026Roundtrip • Montreal (YUL) - Saint Martin (SXM)YUL - SXM • 1 stop SXM - YUL • 1 stopCA $2,766CA $1,792found 1 day agoper traveller - Princess Heights Luxury Boutique Condo Hotel
Aug 12 - Aug 18Princess Heights Luxury Boutique Condo Hotel + Flight
Oyster Pond5 nights9.2/10 - Wonderful (1,002 reviews)"We stayed it a studio. It was ok. Room needs updating but clean. Facility very high up so be prepared for that drive. Was a little scary if you not used to mountain driving actually. Checking in building was very confusing to get to so good luck."Reviewed May 23, 2026Roundtrip • Halifax (YHZ) - Saint Martin (SXM)YHZ - SXM • 2 stops SXM - YHZ • 2 stopsCA $1,658CA $1,127found 1 day agoper traveller
Where to stay in Vineyard
Find the best Vineyard areas and neighborhoods for the activities you enjoy most. Learn more about Vineyard
Indigo Bay
While Indigo Bay isn't home to many top sights, Indigo Beach and Little Bay Beach are some notable places to visit nearby.
Vineyard Hotel Deals
The Morgan Resort Spa Village
2 Beacon Hill Road Simpson Bay
Fully refundableReserve now, pay when you stay
The price is CA $343 per night from Jun 25 to Jun 26
CA $343
CA $447 total
Jun 25 - Jun 26
includes taxes & fees
9/10 Wonderful! (2,171 reviews)
"Perfect location right in walking distance to Maho Beach and Mullet Bay Beach! So cute and the staff was very friendly!"
Reviewed on May 24, 2026
Sonesta Maho Beach All Inclusive Resort Casino & Spa
1 Rhine Road Lowlands
The price is CA $510 per night from Jun 16 to Jun 17
CA $510
CA $617 total
Jun 16 - Jun 17
includes taxes & fees
8/10 Very Good! (2,948 reviews)
"Clean, friendly and accessible"
Reviewed on May 24, 2026
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
Fully refundableReserve now, pay when you stay
The price is CA $284 per night from Jun 15 to Jun 16
CA $284
CA $348 total
Jun 15 - Jun 16
includes taxes & fees
9/10 Wonderful! (1,751 reviews)
"Good location to town but huge property. Be prepared to walk!"
Reviewed on May 25, 2026
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.
Frequently asked questions
Discover the most popular places to visit in Vineyard
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.
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.
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.
Things to do
Half Day Snorkeling Adventure
CA $89
per adult
100% of travellers recommend
High-Speed Ferry to St. Barths
CA $103
per adult
80% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
CA $116
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.