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.
Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

4 out of 5
Price was CA $2,408, price is now CA $1,757 per person
CA $1,757
per person
Nov 1 - Nov 8
found 21 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9/10 Wonderful! (1,084 reviews)
The staff was very friendly and professional. They made us feel welcome. The view from our room was breathtaking and the beach was beautiful. The only thing I didn't like was the restaurant. No many options an a bit pricey. But it didn't matter since the hotel is close to many dining options. Looking forward to my next trip!

Reviewed on Aug. 30, 2025

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was CA $2,920, price is now CA $1,853 per person
CA $1,853
per person
Nov 1 - Nov 8
found 21 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9.2/10 Wonderful! (1,227 reviews)
Family friendly and staff are exceptional.

Reviewed on Aug. 31, 2025

La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was CA $2,725, price is now CA $1,854 per person
CA $1,854
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
9.4/10 Exceptional! (587 reviews)
Great location, clean property

Reviewed on Aug. 26, 2025

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Price was CA $3,687, price is now CA $2,615 per person
CA $2,615
per person
Nov 1 - Nov 8
found 21 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) 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

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was CA $3,291, price is now CA $2,438 per person
CA $2,438
per person
Nov 1 - Nov 8
found 21 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9/10 Wonderful! (1,838 reviews)
Beautiful stay and wonderful people! Thank you

Reviewed on Aug. 29, 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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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

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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 $210 per night from Sep 1 to Sep 2
CA $210
CA $252 total
Sep 1 - Sep 2
includes taxes & 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
The price is CA $342 per night from Sep 1 to Sep 2
CA $342
CA $462 total
Sep 1 - Sep 2
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 $153 per night from Sep 1 to Sep 2
CA $153
CA $184 total
Sep 1 - Sep 2
includes taxes & 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.
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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.