Upper Prince's Quarter Vacation Packages
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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.
Top Upper Prince's Quarter Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Villas at Simpson Bay Resort
Pelican Key
CA $1,713
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,484 reviews)
Just stayed here solo for three nights it was clean and perfect location lived the swim up bar and there are a couple restaurants on site and others right within walking distance this is the best side to stay on right on the heart of everything and not far from everything else! Great resort it looks a bit dated in the rooms but very spacious and comfortable!
Reviewed on Aug 10, 2026
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
CA $1,528
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,003 reviews)
This property is nice.. it almost felt deserted as we didn’t see anyone at night. It was very clean, comfortable and we had everything needed. My only complaint was the room needed more light. I’d stay here again .
Reviewed on Aug 8, 2026
Holland House Beach Hotel
Downtown Philipsburg
CA $1,615
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,006 reviews)
Very nice hotel, centrally located. The staff were very nice. My only complaint, the bathroom was very nice looking, but not functional.
Reviewed on Aug 10, 2026
La Playa Orient Bay
CA $1,230
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.4/10 Exceptional! (768 reviews)
The overall property was nice. There was mold on the ceiling from water leaking in the unit above. The shower leaks a lot of water onto the floor and the toilet rocks and needs tightened to the floor. The light above the kitchen sink only stays on a few seconds. The room was clean and overall resort was nice.
Reviewed on Aug 6, 2026
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 0.64 kilometres 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.
Ready to book your vacation to Upper Prince's Quarter?
Upper Prince's Quarter Hotel Deals
Oyster Bay Beach Resort
10 Emerald Merit Rd Oyster Pond
Fully refundableReserve now, pay when you stay
CA $229
CA $275 total
Aug 11 - Aug 12
includes taxes & fees
8.8/10 Excellent! (1,011 reviews)
"My stay was good. The staff is helpful. The food is good. The pool is big and deep. Loved the hot tub. I was able to get a car to rent on the property and the bed was very comfortable. I would definitely return."
Reviewed on Aug 10, 2026
JW Marriott St. Maarten Beach Resort & Spa
144 Oyster Pond Resort Oyster Pond Sint Maarten
CA $500
CA $645 total
Aug 11 - Aug 12
includes taxes & fees
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond Road No 156 Oyster Pond
Fully refundableReserve now, pay when you stay
CA $207
CA $248 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (1,010 reviews)
"This property is nice.. it almost felt deserted as we didn’t see anyone at night. It was very clean, comfortable and we had everything needed. My only complaint was the room needed more light. I’d stay here again ."
Reviewed on Aug 8, 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.
Stay 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
Half Day Snorkeling Adventure
CA $91
per adult
100% of travellers recommend
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
CA $190
per adult
90% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
CA $120
per adult
94% of travellers recommend
Frequently asked questions
How much does an Upper Prince's Quarter vacation package cost?
Offering great value package deals from CA $1,077 on Expedia, you'll be pleasantly surprised at how much a vacation to Upper Prince's Quarter costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Upper Prince's Quarter?
If you're hoping to score a cheap Upper Prince's Quarter vacation package, consider planning a trip in September, October and November. You'll typically find better rates on hotels and airfares during these months — perfect for budget-conscious travellers.
How many days is enough for Upper Prince's Quarter?
We'd suggest booking an Upper Prince's Quarter vacation for a minimum of 5 days. This will allow you enough time to visit top attractions including Sint Maarten Park and Guana Bay Beach, and also explore neighbourhoods like Little Bay and Madame's Estate. You might even be able to fit in a day trip (or two) from Upper Prince's Quarter.
How to find the best Upper Prince's Quarter package deals?
Landing a cheap Upper Prince's Quarter package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, add a couple of filters and browse what's available. You can fine-tune your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Upper Prince's Quarter package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book an Upper Prince's Quarter vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component individually. And you'll still have the freedom to create a customized Upper Prince's Quarter vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Upper Prince's Quarter?
Score amazing discounts by booking your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Upper Prince's Quarter trip.
How to plan a trip to Upper Prince's Quarter?
- Choose when to travel: Check your schedule and get packing. Your preferred time of year and the available activities will also help you decide when to escape to Upper Prince's Quarter.
- Budget wisely: As well as the price of your hotel, you'll need to consider other expenses. These include food, transportation and flights. Also, set aside a little extra for unexpected costs that may come up during your trip to Upper Prince's Quarter.
- Determine how many days away: Start by making a list of all the attractions and activities you'd like to get to in Upper Prince's Quarter. Then, estimate how long you'll need at each, along with any travel time.
- Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to pick an Upper Prince's Quarter vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
