Upper Prince's Quarter Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was CA $1,834, price is now CA $1,162 per person
CA $1,162
per person
Nov 20 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) 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
Price was CA $2,857, price is now CA $1,403 per person
CA $1,403
per person
Nov 20 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,227 reviews)
No welcome drinks when we arrived. Limited excursions on certain days.

Reviewed on Sep. 2, 2025

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was CA $2,476, price is now CA $1,279 per person
CA $1,279
per person
Nov 16 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,291 reviews)
The property is beautiful, service reps were great. Food on the resort was delicious, excursions provided were very nice. It was affordable, but you do get what you pay for. I chose the least expensive room, and it was very nice, but the furthest away from everything, except its own pool, so lots of walking in the heat. The toilet and sink leaked. I called twice and no one came and it was never fixed. I ended up putting towels on the floor behind the toilet and next to the sink to absorb the water. We were leaving 2 1/2 days later, so I didn’t pursue it. Hopefully it’s fixed for the next customer. If I ever go back to St Martin, I would stay again in a different section of the resort.

Reviewed on Sep. 2, 2025

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Price was CA $3,040, price is now CA $1,757 per person
CA $1,757
per person
Nov 20 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) 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

Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

4 out of 5
Price was CA $1,815, price is now CA $1,170 per person
CA $1,170
per person
Nov 20 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,084 reviews)
Bar staff was the best from Morgan and her team.

Reviewed on Sep. 2, 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
Default Image

Point Blanche

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

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

Ready to book your vacation to Upper Prince's Quarter?

 

Choose your dates

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
The price is CA $211 per night from Sep 4 to Sep 5
CA $211
CA $253 total
Sep 4 - Sep 5
includes taxes & fees
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
The price is CA $343 per night from Sep 4 to Sep 5
CA $343
CA $464 total
Sep 4 - Sep 5
includes taxes & 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
The price is CA $154 per night from Sep 4 to Sep 5
CA $154
CA $184 total
Sep 4 - Sep 5
includes taxes & fees
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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

Great Bay Beach

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
Fort Amsterdam which includes château or palace, a ruin and military items

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, landscape views and a sandy beach

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

CA $103
per adult
76% of travellers recommend
High-Speed Ferry to St. Barths
Lunch at Meads BAy

Ultimate Prickly Pear and Anguilla Experience

CA $205
per adult
82% 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

CA $77
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.