Upper Prince's Quarter Vacations from $853
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Your Upper Princes Quarter Vacation
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.
The Latest Upper Prince's Quarter vacation packages
Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
$1,007
per person
Oct 24 - Oct 31
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,000 reviews)
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
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See all available trips from Columbus to Upper Prince's Quarter
View all tripsStay near popular Upper Prince's Quarter attractions
Guana Bay Beach
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.
Port of St. Maarten
Explore the waterfront in Philipsburg with a trip to Port of St. Maarten.
Gibb's Bay Beach
8.0/10 (27 reviews)
Why not spend a lazy afternoon at Gibb's Bay Beach during your trip to Upper Prince's Quarter?
What to do in Upper Prince's Quarter
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
$159
per adult
90% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
$77
per adult
94% of travellers recommend
Upper Prince's Quarter Hotel Deals
Oyster Bay Beach Resort
10 Emerald Merit Rd Oyster Pond
Fully refundableReserve now, pay when you stay
$202 nightly
$211 total
Sep 17 - Sep 18
Total with taxes and fees
JW Marriott St. Maarten Beach Resort & Spa
144 Oyster Pond Resort Oyster Pond Sint Maarten
$443 nightly
$463 total
Sep 17 - Sep 18
Total with taxes and fees
8.8/10 Excellent! (401 reviews)
"Spacious property all and all and staff members were all kind and courteous. I already recommended to friends and family. It is a little out of the way but the island is small so average 15 to 20 mins."
Reviewed on Sep 15, 2026
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond Road No 156 Oyster Pond
Fully refundableReserve now, pay when you stay
$199 nightly
$208 total
Sep 17 - Sep 18
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
"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
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.
Find the Best Upper Prince's Quarter Vacation Packages
Upper Prince's Quarter Beach Vacation
Listen to the sound of waves crashing onto the shore and kick back by the shimmering waters on your Upper Prince's Quarter vacation. If you just need to get away, a trip to Upper Prince's Quarter will work wonders. We have a great range of Upper Prince's Quarter vacation deals to select from. Snap up one close to Guana Bay Beach, just 0.4 miles from the downtown area, and live out your vacation fantasies without hurting your budget.
Things You Should Know About Upper Prince's Quarter
- If your idea of the perfect vacation includes luxuries like staying just steps from the beach, the scent of salty air drifting through your window and crashing waves lulling you to sleep, browse our Upper Prince's Quarter beach hotels.
- Another type of place to stay is villas. Look up JW Marriott St. Maarten Beach Resort & Spa and Princess Heights Luxury Boutique Condo Hotel and see which suits your style.
Upper Princes Quarter Essential Information
Language | Dutch |
|---|---|
Currency | Netherlands Antillean guilders |
Local Welcome | Hallo |
Local Goodbye | Dag |
Closest Airport | Princess Juliana Intl. Airport (SXM) |
Top Sights | Sint Maarten Park, Little Bay Beach and Guana Bay Beach |
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Frequently asked questions
How much does an Upper Prince's Quarter vacation package cost?
You'll find cheap prices from $853 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.
What are the cheapest months to go to Upper Prince's Quarter?
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.
How many days is enough for Upper Prince's Quarter?
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.
How to find the best Upper Prince's Quarter package deals?
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.
Is it cheaper to book an Upper Prince's Quarter vacation as a package?
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.
When to book a vacation package to Upper Prince's Quarter?
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.
How to plan a trip to Upper Prince's Quarter?
- Choose your travel dates: The things you plan to do in Upper Prince's Quarter and your favorite season will help you decide when to get away.
- Calculate your budget: Ensure you have enough money to cover everything from transportation and meals to activities and flights. Your accommodations will probably be the largest expense during your trip to Upper Prince's Quarter.
- Use our trip planning tool to discover Upper Prince's Quarter: Research every aspect of your trip to Upper Prince's Quarter with this comprehensive planner. Invite family or friends to collaborate on a group trip, search for hotels or things to do and make bookings.
- Decide your trip length: Think about how much time you'd like to spend discovering Upper Prince's Quarter. Plan your days so you can get to all the activities and attractions you're interested in at a leisurely pace.
- Combine your airfare and accommodations: Once you've nailed down your trip dates and duration, lock in the perfect Upper Prince's Quarter vacation package for you.
- Book experiences or activities ahead of time: Whether it's entrance to a big attraction or a day trip in nature, you won't have to worry about missing out on Upper Prince's Quarter's best offerings. Find all the fun things to do in Upper Prince's Quarter in Upper Prince's Quarter with our dedicated travel guide.
Does Expedia offer Book Now, Pay Later Upper Prince's Quarter vacation packages?
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.
