Vineyard Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Vineyard Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Sapphire Beach Club Resort
Maho
Price was $1,175, price is now $814 per person
$814
per person
Mar 12 - Mar 18
found 17 hours ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
Book a stay at this beach resort in Lowlands. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
The Villas at Simpson Bay Resort
Price was $3,994, price is now $1,880 per person
$1,880
per person
Mar 12 - Mar 18
found 17 hours ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maho Beach and Orient Bay Beach are located nearby.
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Save 100% on your flight
Price was $2,061, price is now $1,069 per person
$1,069
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
Book a stay at this family-friendly hotel in Oyster Pond. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Orient Bay Beach and Grand Case Beach are located nearby.
Holland House Beach Hotel
Downtown Philipsburg
Save 100% on your flight
Price was $2,802, price is now $1,747 per person
$1,747
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
Book a stay at this beach hotel in Philipsburg. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Orient Bay Beach and Maho Beach are located nearby.
Divi Little Bay Beach Resort
Save 100% on your flight
Price was $2,887, price is now $1,946 per person
$1,946
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
Book a stay at this beach resort in Philipsburg. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maho Beach and Orient Bay Beach are located nearby.
Oceans at Divi Little Bay
Save 100% on your flight
Price was $2,472, price is now $1,685 per person
$1,685
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
Stay at this hotel in Philipsburg. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Maho Beach and Orient Bay Beach are located nearby.
Top Hotel Deals
The Morgan Resort Spa Village
2 Beacon Hill Road Simpson Bay
8.82 km from Vineyard
Book a stay at this spa resort in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. ...
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
6.17 km from Vineyard
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our ...
Sonesta Maho Beach All Inclusive Resort Casino & Spa
1 Rhine Road Lowlands
9.01 km from Vineyard
Book a stay at this beach property in Lowlands. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the clean rooms ...
Hilton Vacation Club Flamingo Beach St. Maarten
Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay
6.13 km from Vineyard
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. ...
The Villas at Simpson Bay Resort
Billy Folly Road No. 37A Simpson Bay
5.91 km from Vineyard
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our ...
Oyster Bay Beach Resort
10 Emerald Merit Rd Oyster Pond
4.12 km from Vineyard
Book a stay at this beach resort in Oyster Pond. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
Fourteen at Mullet Bay
2 University Drive, Cupecoy Lowlands
10.03 km from Vineyard
Book a stay at this beach aparthotel in Lowlands. Enjoy free WiFi, free parking, and a casino. Our guests praise the helpful staff in our reviews. Popular attractions ...
Hommage Hotel & Residences
Route des Terres Basses BP 172 Nettle Bay
9.14 km from Vineyard
Book a stay at this spa hotel in Nettle Bay. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our ...
Sonesta Ocean Point All Inclusive, Adults Only Resort
1A Rhine Rd. Lowlands
9.17 km from Vineyard
Book a stay at this luxury property in Lowlands. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in ...
Divi Little Bay Beach Resort
Little Bay Road Philipsburg
2.34 km from Vineyard
Book a stay at this beach resort in Philipsburg. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff and the clean rooms ...
Hilton Vacation Club Royal Palm St. Maarten
115 Welfare Road Simpson Bay
6.14 km from Vineyard
Book a stay at this beach aparthotel in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property ...
JW Marriott St. Maarten Beach Resort & Spa
144 Oyster Pond Resort Oyster Pond Sint Maarten
3.57 km from Vineyard
Book a stay at this luxury hotel in Oyster Pond. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
The Atrium Beach Resort and Spa, an Ascend Collection Resort
6 Billy Folly Road Simpson Bay
5.85 km from Vineyard
Book a stay at this beach hotel in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Dec 23 - Sat, Dec 27
FLL
Fort Lauderdale - Hollywood Intl.
SXM
Princess Juliana Intl.
$247 Roundtrip, found 1 day ago
$247
Roundtrip
found 1 day ago
Mon, Feb 9 - Wed, Feb 18
PHL
Philadelphia Intl.
SXM
Princess Juliana Intl.
$250 Roundtrip, found 5 days ago
$250
Roundtrip
found 5 days ago
Mon, Jan 19 - Thu, Jan 29
JFK
John F. Kennedy Intl.
SXM
Princess Juliana Intl.
$283 Roundtrip, found 1 day ago
$283
Roundtrip
found 1 day ago
Sun, Jan 18 - Sat, Jan 31
JFK
John F. Kennedy Intl.
SXM
Princess Juliana Intl.
$347 Roundtrip, found 1 day ago
$347
Roundtrip
found 1 day ago
Fri, Jan 16 - Sat, Jan 31
JFK
John F. Kennedy Intl.
SXM
Princess Juliana Intl.
$358 Roundtrip, found 1 day ago
$358
Roundtrip
found 1 day ago