Upper Prince's Quarter Vacations from $825

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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

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Save 100% on your flight
Price was $1,471, price is now $825 per person
$825
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (960 reviews)
Its a beautiful property and the customer service experience is wonderful

Reviewed on Aug 30, 2025

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
Price was $1,785, price is now $920 per person
$920
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,227 reviews)
Nice place, close to a publuc beach, also has a private beach. Great weather even though it was hurricane season

Reviewed on Aug 31, 2025

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Save 100% on your flight
Price was $2,669, price is now $1,492 per person
$1,492
per person
Nov 22 - Nov 29
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (1,291 reviews)
Rough check in and check out process, overall good needs more staff. Rooms were nice this is a big property so be sure which side you are booking. 10am checkout is horrible especially with a 4pm check in time

Reviewed on Aug 31, 2025

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Save 100% on your flight
Price was $1,752, price is now $981 per person
$981
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,003 reviews)
Wonderful stay. Only issue is the WiFi for the TV wasn’t stable but all else was amazing!

Reviewed on Aug 27, 2025

La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $2,019, price is now $1,227 per person
$1,227
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.4/10 Exceptional! (587 reviews)
Great location, clean property

Reviewed on Aug 26, 2025

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Where to stay in Upper Prince's Quarter

Find the best Upper Prince's Quarter areas and neighborhoods for the activities you enjoy most. Learn more about Upper Prince's Quarter
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Point Blanche

4/5(5 area reviews)

While Point Blanche isn't home to many top sights, Great Bay Beach and Little Bay Beach are some notable places to visit nearby.

Find hotels in Point Blanche

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

4.5/5(88 reviews)

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
Philipsburg Boardwalk

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

2/5(2 reviews)

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

High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

$75
per adult
76% of travellers recommend
High-Speed Ferry to St. Barths
Lunch at Meads BAy

Ultimate Prickly Pear and Anguilla Experience

$149
per adult
84% of travellers recommend
Ultimate Prickly Pear and Anguilla Experience
Sightseeing Tour of the French and Dutch Sides of the Island

St-Martin and St Maarten: Sightseeing Tour of the French and Dutch Sides of the Island

$56
per adult
80% of travellers recommend
St-Martin and St Maarten: Sightseeing Tour of the French and Dutch Sides of the Island
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
$189 nightly
The price is $197 total per night from Sep 2 to Sep 3
$197 total
Sep 2 - Sep 3
Total with taxes and fees
8.4/10 Very Good! (917 reviews)
"Everything was very nice. The free breakfast was very limited- contintental breakfast. The hotel shuttle was a local taxi & cost $35. We needed an accommodation for our big anniv. celebration but nobody seemed to help us nor provide for us, which was a bottle of cider instead of alcohol. That was ..."

Reviewed on Aug 25, 2025

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, Building A, Oyster Pond, Sint Maarten
$319 nightly
The price is $336 total per night from Sep 2 to Sep 3
$336 total
Sep 2 - Sep 3
Total with taxes and fees
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, Dawn Beach, Oyster Pond
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $134 total per night from Sep 2 to Sep 3
$134 total
Sep 2 - Sep 3
Total with taxes and fees
9.2/10 Wonderful! (953 reviews)
"This property was very nice and astonishing. The area was quiet and lovely place to have a vacation at. The beds were so comfortable after a day of activities and excursions. The place is very peaceful and beautiful. The staff were amazing as well. The views were amazing. I would definitely ..."

Reviewed on Aug 15, 2025

Princess Heights Luxury Boutique Condo Hotel
See all 3,589 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.

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

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Frequently asked questions

How much does an Upper Prince's Quarter vacation package cost?
You'll find cheap prices from $825 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.