Upper Prince's Quarter Vacations from $771

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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.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Save 100% on your flight
Price was $1,261, price is now $771 per person
$771
per person
May 15 - May 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
8.6/10 Excellent! (952 reviews)
Room was clean, and service was good. Pretty expensive and return on value is lacking.

Reviewed on Feb 20, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was $2,179, price is now $933 per person
$933
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (1,463 reviews)
Friendly staff, all inclusive resort, decent restaurants, beach and ocean swimming.

Reviewed on Feb 20, 2026

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Save 100% on your flight
Price was $1,669, price is now $842 per person
$842
per person
May 15 - May 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (973 reviews)
Room was quite clean and commodious. Staff was accessible and friendly.

Reviewed on Feb 21, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Save 100% on your flight
Price was $2,605, price is now $1,474 per person
$1,474
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,309 reviews)
*Modern clean rooms. *Having a few dishes, microwave, mini-fridge turned out to be handy. *Staff was very friendly. *Breakfast buffet was excellent. *Onsite restaurants and many nearby was nice. *Broad selection at the Replay Restaurant & Bar. It was the only one we ate at twice.

Reviewed on Feb 21, 2026

La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,788, price is now $1,083 per person
$1,083
per person
May 15 - May 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.4/10 Exceptional! (604 reviews)
Amenities were excellent, the staff was very courteous.

Reviewed on Feb 19, 2026

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Discover the most popular places to visit in Upper Prince's Quarter

Great Bay Beach showing general coastal views, a sandy beach and a coastal town

Great Bay Beach

If a restful vacation is part of your travel plans, Great Bay Beach might be the perfect place to seek out during your trip to Philipsburg. Check out the shops and top-notch restaurants in this romantic area.

Great Bay Beach
Captain Hodge Pier in Philipsburg, Saint Martin, Caribbean

Philipsburg Boardwalk

Philipsburg Boardwalk is just one of the places to see in Philipsburg, so why not enjoy the other things to explore during your travels? Stroll along the area's beaches or simply enjoy its restaurants.

Philipsburg Boardwalk
Fort Amsterdam showing building ruins, military items and a castle

Fort Amsterdam

The remains of the first Dutch military base in the Caribbean offer stunning views across the ocean and over the town of Philipsburg behind it.

Fort Amsterdam

What to do in Upper Prince's Quarter

Panoramic view of vibrant St. Martin

Edge Ferry Tickets to St. Barts

$100
per adult
84% of travellers recommend
Edge Ferry Tickets to St. Barts
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

$135
per adult
90% of travellers recommend
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
Sand Dollar Snorkeling Adventure

Half Day Snorkeling Adventure

$65
per adult
100% of travellers recommend
Half Day Snorkeling Adventure
See all activities in Upper Prince's Quarter

Upper Prince's Quarter Hotel Deals

Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
10 Emerald Merit Rd Oyster Pond
Fully refundableReserve now, pay when you stay
$300 nightly
The price is $313 total per night from Mar 1 to Mar 2
$313 total
Mar 1 - Mar 2
Total with taxes and fees
8.6/10 Excellent! (1,008 reviews)
Room was clean, and service was good. Pretty expensive and return on value is lacking.

Reviewed on Feb 20, 2026

Oyster Bay Beach Resort
JW Marriott St. Maarten Beach Resort & Spa

JW Marriott St. Maarten Beach Resort & Spa

5 out of 5
144 Oyster Pond Resort Oyster Pond Sint Maarten
$817 nightly
The price is $854 total per night from Mar 20 to Mar 21
$854 total
Mar 20 - Mar 21
Total with taxes and fees
8.6/10 Excellent! (255 reviews)
Great staff, spotless resort. Day manager, she was awesome.

Reviewed on Feb 21, 2026

JW Marriott St. Maarten Beach Resort & Spa
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond Road No 156 Oyster Pond
Fully refundableReserve now, pay when you stay
$336 nightly
The price is $351 total per night from Mar 1 to Mar 2
$351 total
Mar 1 - Mar 2
Total with taxes and fees
9.2/10 Wonderful! (1,005 reviews)
Room was quite clean and commodious. Staff was accessible and friendly.

Reviewed on Feb 21, 2026

Princess Heights Luxury Boutique Condo Hotel
See all 3,512 properties 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.

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

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 $771 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.