Upper Prince's Quarter Holidays

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Top Flight + Hotel Deals in Upper Prince's Quarter

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
per person
19 Oct - 26 Oct
found 1 day ago
Return direct flight included
Lyon (LYS) to Philipsburg (SXM)
8.6/10 Excellent! (891 reviews)
Parking not much parking and very tight spaces

Reviewed on 29 Jul 2025

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
per person
19 Oct - 26 Oct
found 1 day ago
Return direct flight included
Lyon (LYS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,192 reviews)
Food options were good, beds were comfortable, Internet access was good for the most part, and access to transportation was good. It was easy to get a taxi right outside of the resort. The staff at the restaurants and bars were absolutely amazing.

Reviewed on 29 Jul 2025

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
per person
19 Oct - 26 Oct
found 1 day ago
Return direct flight included
Lyon (LYS) to Philipsburg (SXM)
9.2/10 Wonderful! (938 reviews)
The hotel was a great place to stay. The staff was great and the place is beautiful.

Reviewed on 28 Jul 2025

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
per person
19 Oct - 26 Oct
found 1 day ago
Return direct flight included
Lyon (LYS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,000 reviews)
This is in the area of cruises so everything closes around 5. A taxi is definitely needed to go places in the evening

Reviewed on 26 Jul 2025

Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
per person
19 Oct - 26 Oct
found 1 day ago
Return direct flight included
Lyon (LYS) to Philipsburg (SXM)
8.4/10 Very Good! (1,003 reviews)
The hotel was not what was advertised. First of all, pictures showed a giant pool when there were three pools, each smaller than the next. Then, it was pathetic an all-inclusive. The breakfast buffet was tiny. There was little to no fruit available at any meal. There was no water in the room. You had to ask for it at the bar. Unlike any other all inclusive where I have stayed any all inclusive benefits ended at breakfast even if you were departing in the afternoon. The bartender at the pool bar was exceptional as was the woman who cleaned my room 330. Some other employees seemed disinterested and did not even make eye contact.

Reviewed on 25 Jul 2025

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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Dawn Beach Estates

When in Dawn Beach Estates, you can plan a visit to Dawn Beach and Oyster Bay Marina, some noteworthy sights in the nearby area.

Find hotels in Dawn Beach Estates

Upper Prince's Quarter Beach Holiday

Listen to the sound of waves crashing onto the shore and kick back by the shimmering waters on your Upper Prince's Quarter holiday. 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 holiday deals to select from. Snap up one close to Guana Bay Beach, just 0.64 kilometres from the downtown area, and live out your holiday fantasies without hurting your budget.

Things You Should Know About Upper Prince's Quarter

Top hotels in Upper Prince's Quarter

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
The price is €375 per night from 31 Jul to 1 Aug
€375
31 Jul - 1 Aug
includes taxes & fees
8.8/10 Excellent! (192 reviews)
"From the moment I arrived, I was enveloped in an atmosphere of warmth and impeccable service. The staff greeted me with genuine smiles and were incredibly efficient during check-in. My room was not only spotless but also beautifully designed, offering a serene space to unwind after a long day. The ..."

Reviewed on 26 Jul 2025

JW Marriott St. Maarten Beach Resort & Spa
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
The price is €170 per night from 2 Aug to 3 Aug
€170
2 Aug - 3 Aug
includes taxes & fees
8.4/10 Very Good! (903 reviews)
"Parking not much parking and very tight spaces"

Reviewed on 29 Jul 2025

Oyster Bay Beach Resort
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
9.2/10 Wonderful! (943 reviews)
Wonderful stay!
"Wonderful stay! Front desk was excellent and room very spacious. Did find minor cleaning issues but would stay again. People complained about being too many stairs but I didn’t have that issue, guess it depends on what floor you are assigned to."

Reviewed on 29 Jul 2025

Get rates
Princess Heights Luxury Boutique Condo Hotel
See all 3,588 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.

Popular places to visit

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 heritage elements, building ruins 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
Guana Bay Beach featuring cuddly or friendly animals, tropical scenes and landscape views

Guana Bay Beach

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.

Guana Bay Beach

What to do in Upper Prince's Quarter

High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

€65
per adult
76% of travellers recommend
High-Speed Ferry to St. Barths
Lunch at Meads BAy

Ultimate Prickly Pear and Anguilla Experience

€128
per adult
82% of travellers recommend
Ultimate Prickly Pear and Anguilla Experience
At the border!

4-Hour Guided ATV/QUAD Tour of Sint Maarten/St. Martin

€86
per traveller
100% of travellers recommend
4-Hour Guided ATV/QUAD Tour of Sint Maarten/St. Martin
See all activities in Upper Prince's Quarter

Frequently asked questions

How much does an Upper Prince's Quarter holiday package cost?
You'll find cheap prices from €1,911 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 holiday to Upper Prince's Quarter costs.
What are the cheapest months to go to Upper Prince's Quarter?
If you'd like to snag a cheap Upper Prince's Quarter holiday package, consider planning a trip in September, October and November. You'll typically find better rates on flights and accommodation during these months — ideal for budget-conscious travellers.
How many days is enough for Upper Prince's Quarter?
The ideal length for your Upper Prince's Quarter holiday depends on what you'd like to see and do. Usually, a handful of days to a week will give you plenty of time to hit all the leading attractions and discover some hidden gems along the way.
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 holiday as a package?
You can enjoy significant savings on your Upper Prince's Quarter break by booking a tailored holiday 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 holiday 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 when to travel: Check your schedule and pack your bags. Your preferred time of year and the type of activities on offer will also help you decide when to escape to Upper Prince's Quarter.
  2. Budget wisely: In addition to the cost of your accommodation, you'll need to consider other expenses too. These include flights, food and transportation. Also, put aside a little extra for unexpected costs that could crop up during your trip to Upper Prince's Quarter.
  3. Set the duration of your trip: Start by listing all the activities and sights you'd like to experience in Upper Prince's Quarter. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a customised Upper Prince's Quarter holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.