Photo by Third Avenue Lady
Reserve a Upper Princes Quarter vacation package and prepare to experience everything this city has to offer. Think about staying in the neighborhood of Maho, which is great for dining, golfing and coastal beaches. You'll want to do some exploring during your trip to Upper Princes Quarter. Don't miss major attractions such as Little Bay Beach, Sint Maarten Park and Guana Bay Beach. Expedia is here to help you escape the everyday. Tailor your vacation to Upper Princes Quarter to match your travel style, whatever that may look like.
Price found within the past 48 hours. Click for updated prices.
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Feb 5 - Feb 9
Simpson Bay
4 nights
9.0/10 - Wonderful (2,426 reviews)
Roundtrip • Boston (BOS) - Saint Martin (SXM)
BOS - SXM • 1 stop SXM - BOS • 1 stop
Save 100% on your flight
$1,036
per traveler
found 1 day ago
Jan 20 - Jan 25
Pelican Key
5 nights
9.2/10 - Wonderful (1,616 reviews)
"I wish I would have dug deeper on this resort. I have spent all week trying to figure out how in the world they have good reviews. Then my group and I figured out, they have the employees make comments and reviews. Well let me tell you, they charge you $10 to use the gym per day, there is no food anywhere. You have to venture out and try to find it on the resort. This place is like a nursing home and all that is here is 80 years old and older. I watched two geriatrics this week get taken out in..."
Reviewed November 14, 2026
Roundtrip • Boston (BOS) - Saint Martin (SXM)
BOS - SXM • 1 stop SXM - BOS • 1 stop
$1,573
per traveler
found 1 day ago
Jan 19 - Jan 23
Pelican Key
4 nights
9.0/10 - Wonderful (2,185 reviews)
Roundtrip • New York (NYC) - Saint Martin (SXM)
JFK - SXM • Nonstop SXM - LGA • 1 stop
$1,133
per traveler
found 2 days ago
Jan 2 - Jan 8
Oyster Pond
6 nights
9.2/10 - Wonderful (1,000 reviews)
Roundtrip • Boston (BOS) - Saint Martin (SXM)
BOS - SXM • 1 stop SXM - BOS • 2 stops
$1,249
per traveler
found 1 day ago
Dec 22 - Dec 26
Philipsburg
4 nights
8.2/10 - Very good (1,002 reviews)
"The beach is stunning! The beds suck, you feel every coil in the king beds. We had multiple rooms booked in our party and everyone had the same complaints. Bar staff was not friendly upon learning we had the all inclusive option with staff often telling us they were going on break or serving us last. Food was fresh and delicious but the buffet for dinner never opened and was Italian every single night despite the sign representing every night was a different theme. Plenty of beach and pool..."
Reviewed November 14, 2026
Roundtrip • Boston (BOS) - Saint Martin (SXM)
BOS - SXM • Nonstop SXM - BOS • Nonstop
$1,686
per traveler
found 1 day ago
Rating: 9.0/10 (92 reviews)
The picturesque shores of this tranquil bay provide a great opportunity to escape the crowds and jump in the crystal clear water for surfing or swimming.
Explore the waterfront in Philipsburg with a trip to Port of St. Maarten.
Rating: 8.0/10 (27 reviews)
Why not spend a lazy afternoon at Gibb's Bay Beach during your trip to Upper Prince's Quarter?
$65
per adult
100% of travelers recommend
$77
per adult
94% of travelers recommend
$135
per adult
86% of travelers recommend
See all activities in Upper Prince's Quarter
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.
See all properties in Upper Prince's Quarter
You'll find cheap prices from $1,036 on Expedia for your Upper Prince's Quarter break. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Upper Prince's Quarter costs.
You're likely to find lower rates and greater availability in July, October and December. Browse our cheap Upper Prince's Quarter vacation packages and you could land some great off-season deals.
With a well-organized schedule, you can easily tick off the main Upper Prince's Quarter sights in a few days. But if you want to explore off the beaten track or take day trips, consider booking your Upper Prince's Quarter vacation for longer.
Begin your search for an Upper Prince's Quarter package deal by entering your destination and travel dates under our "Packages" tab. Then select some filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Upper Prince's Quarter package deal straight away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Upper Prince's Quarter escape underway.
You can enjoy significant savings on your Upper Prince's Quarter break by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to view the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
Land amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Upper Prince's Quarter getaway.
If you're anything like us, you love traveling but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Upper Prince's Quarter vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.