Search Deals onCupecoy Vacation Packages
Cupecoy Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Oyster Bay Beach Resort
Price was $942, price is now $670 per person
$670
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Book a stay at this spa resort in Oyster Pond. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Orient Bay and Port of St. Maarten are located nearby.

Simpson Bay Resort, Marina & Spa
Save 100% on your flight
Price was $1,497, price is now $872 per person
$872
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 Mullet Bay Beach are located nearby.
Old resort being maintained.
Reviewed on Sep 15, 2026

Princess Heights Luxury Boutique Condo Hotel
Price was $1,140, price is now $739 per person
$739
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 Port of St. Maarten and Orient Bay are located nearby.
The staff is very friendly and accommodating. Beautiful views. The only thing I would ask is that water be restocked daily because it is easy to get dehydrated even if you buy your own water.
Reviewed on Sep 14, 2026

Panorama Residences at Monte Vista
Price was $1,344, price is now $932 per person
$932
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Book a stay at this luxury aparthotel in Philipsburg. Enjoy free WiFi, free parking, and in-room massages. Popular attractions Maho Beach and Port of St. Maarten are located nearby.

La Playa Orient Bay
Save 100% on your flight
Price was $2,089, price is now $1,518 per person
$1,518
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Book a stay at this beach hotel in Orient Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Orient Bay and Grand Case Beach are located nearby.
Fabulous stay! Beautiful resort right on Orient Bay!
Reviewed on Aug 26, 2026

Divi Little Bay Beach Resort
Price was $1,146, price is now $843 per person
$843
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 Port of St. Maarten are located nearby.

Holland House Beach Hotel
Price was $1,179, price is now $874 per person
$874
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 Maho Beach and Port of St. Maarten are located nearby.

Oceans at Divi Little Bay
Price was $1,239, price is now $931 per person
$931
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 Port of St. Maarten are located nearby.
We had a great stay at Divi Little Bay! Everyone we interacted with was incredibly friendly and welcoming, and overall we really enjoyed our time at the resort.
We visited over Labor Day weekend, so one thing I would definitely keep in mind is the time of year. September and October are considered low season in St. Maarten, so we didn’t necessarily get the full experience of the island or resort being super busy. Thankfully, there were still a good amount of people around during Labor Day weekend, so it never felt completely empty. We were told that the week after Labor Day, though, things get much quieter and quite a few restaurants around the island close temporarily for low season, so that is something I would consider when planning your trip.
The resort itself is a good size and very easy to get around. The rooms were also really nice, clean, and spacious, which made the stay very comfortable. I would describe the property as more of a smaller, relaxed Caribbean resort rather than the huge resort experience you might be used to in places like Mexico or the Dominican Republic. If you’re expecting a massive property with tons of restaurants, activities, and entertainment going on at all times, this isn’t really that type of resort. For us, though, the smaller size made it feel relaxed and convenient.
One thing I would recommend to the resort is adding more fans in some of the outdoor areas, especially around Gizmo’s Bar. It gets very hot, and since a lot of the common ar
Reviewed on Sep 14, 2026
Cupecoy Vacation Packages 3-4 Night Stays
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Cupecoy Vacation Packages 5-7 Night Stays
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Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Mon, Oct 26 - Wed, Oct 28
JFK
John F. Kennedy Intl.
SXM
Princess Juliana Intl.
$290 Roundtrip, found 8 hours ago
$290
Roundtrip
found 8 hours ago

Mon, Nov 16 - Fri, Dec 4
BOS
Logan Intl.
SXM
Princess Juliana Intl.
$295 Roundtrip, found 18 hours ago
$295
Roundtrip
found 18 hours ago

Mon, Jan 25 - Wed, Feb 3
YYZ
Pearson Intl.
SXM
Princess Juliana Intl.
$309 Roundtrip, found 2 days ago
$309
Roundtrip
found 2 days ago

Mon, Nov 2 - Thu, Nov 12
EWR
Newark Liberty Intl. Airport
SXM
Princess Juliana Intl.
$325 Roundtrip, found 4 days ago
$325
Roundtrip
found 4 days ago
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