Title: Upper Prince's Quarter Vacation Packages & Trips 2026 from CA $1,218 | Expedia.ca

[Upper Prince's Quarter Travel Guide](https://expedia.ca/Upper-Princes-Quarter.dx553248635976384612)[Hotels in Upper Prince's Quarter](https://expedia.ca/Upper-Princes-Quarter-Hotels.d553248635976384612.Travel-Guide-Hotels)[Vacation Rentals in Upper Prince's Quarter](https://expedia.ca/Upper-Princes-Quarter-Vacation-Rentals.d553248635976384612.Travel-Guide-VacationRentals)[Upper Prince's Quarter Car Rentals](https://expedia.ca/Car-Rentals-In-Upper-Princes-Quarter.d553248635976384612.Car-Rental-Guide)

![](https://images.trvl-media.com/place/6131289/f7ca3e9d-42ab-4e62-9ff0-f351eb8867c8.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# 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](https://www.expedia.ca/Little-Bay-Beach-Philipsburg.d553248621532873750.Vacation-Attraction), [Sint Maarten Park](https://www.expedia.ca/Sint-Maarten-Park-Philipsburg.d553248621533158276.Vacation-Attraction) and [Guana Bay Beach](https://www.expedia.ca/Guana-Bay-Beach-Philipsburg.d506436.Vacation-Attraction). 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](https://images.trvl-media.com/lodging/1000000/570000/561400/561365/3eb207bd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

CA $1,218

per person

Apr 17 - Apr 23

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Philipsburg (SXM)

9.2/10 Wonderful! (973 reviews)

Very nice rooms, pool and workout room. Staff was very nice, friendly and accommodating.

Reviewed on Feb 10, 2026

![Simpson Bay Resort, Marina & Spa](https://images.trvl-media.com/lodging/2000000/1260000/1256900/1256868/30f27be9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Simpson Bay Resort, Marina & Spa

Pelican Key

CA $2,144

per person

Apr 1 - Apr 8

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Philipsburg (SXM)

9/10 Wonderful! (1,463 reviews)

Room was dark, and view was a parking lot. Certainly not what pictures showed.

Reviewed on Feb 13, 2026

![The Villas at Simpson Bay Resort](https://images.trvl-media.com/lodging/5000000/4560000/4553800/4553784/7e74429d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Villas at Simpson Bay Resort

Pelican Key

CA $1,831

per person

Apr 17 - Apr 23

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Philipsburg (SXM)

9.2/10 Wonderful! (1,309 reviews)

The room was clean and the staff was great.

Reviewed on Feb 13, 2026

![Oyster Bay Beach Resort](https://images.trvl-media.com/lodging/2000000/1100000/1095400/1095348/00eb22aa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Oyster Bay Beach Resort

Oyster Pond

CA $1,249

per person

Apr 17 - Apr 23

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Philipsburg (SXM)

8.6/10 Excellent! (952 reviews)

Every one was courteous and helpful. Place was very clean

Reviewed on Feb 13, 2026

![Panorama Residences at Monte Vista](https://images.trvl-media.com/lodging/121000000/120450000/120440200/120440175/89140f9f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Panorama Residences at Monte Vista

Point Blanche

CA $1,636

per person

Apr 17 - Apr 23

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Philipsburg (SXM)

10/10 Exceptional! (1 review)

Like others have stated I was hesitant to book at first with it being a new property and limited reviews but we are glad we did. The whole complex is very modern, secure and as beautiful as the pictures show. The view from the location is amazing. The pool was great and got sun all day, most of the time we had the pool to ourselves. You will definitely want a car as its a 5 minute drive down the hill to any restaurants or stores. Communication could have been better and being a new place there is a lack of kitchen supplies if you are planning to cook in a lot. Overall it was a great stay and we would stay here again.

Reviewed on Feb 8, 2026

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

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[Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_553248635976384612)

## 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

- If your idea of the perfect vacation includes luxuries like staying just steps from the beach, the scent of salty air drifting through your window and crashing waves lulling you to sleep, browse our [Upper Prince's Quarter beach hotels](https://www.expedia.ca/d553248635976384612-tBeachHotel.Travel-Guide-Filter-Hotels?lang=en&rfrr=ATG.LP.BodyContent).
- Another type of place to stay is villas. Look up [JW Marriott St. Maarten Beach Resort & Spa](https://www.expedia.ca/Oyster-Pond-Hotels-The-Westin-Dawn-Beach-Resort-Spa.h93231967.Hotel-Information) and [Princess Heights Luxury Boutique Condo Hotel](https://www.expedia.ca/Oyster-Pond-Hotels-Princess-Heights-Luxury-Boutique-Condo-Hotel.h561365.Hotel-Information) and see which suits your style.

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

Choose your dates

## Upper Prince's Quarter Hotel Deals

![Oyster Bay Beach Resort](https://images.trvl-media.com/lodging/2000000/1100000/1095400/1095348/00eb22aa_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Oyster Bay Beach Resort

10 Emerald Merit Rd Oyster Pond 

CA $355

CA $426 total

Mar 1 - Mar 2

includes taxes & fees

8.6/10 Excellent! (1,007 reviews)

The room, the views, the accommodations… it was all super great!

Reviewed on Feb 7, 2026

[](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=1095348&PinnedHotelID=1095348&HadPinnedHotel=true&regionId=553248635976384612)

![JW Marriott St. Maarten Beach Resort & Spa](https://images.trvl-media.com/lodging/94000000/93240000/93232000/93231967/fd639aa3_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

JW Marriott St. Maarten Beach Resort & Spa

144 Oyster Pond Resort Oyster Pond Sint Maarten

CA $1,020

CA $1,241 total

Feb 26 - Feb 27

includes taxes & fees

8.6/10 Excellent! (247 reviews)

4 star hotel. Outrageous $50 USD per day resort charge added (this is a hotel hidden fee not a government tourist tax). Expensive to get to and travel from by taxi. Lack of breakfast included is a down side. Meals are over priced. $200 USD for a beach/pool bed (these are free at Excellent hotels). ...

Reviewed on Feb 10, 2026

[](https://expedia.ca/Hotel-Search?startDate=26%2F02%2F2026&endDate=27%2F02%2F2026&selected=93231967&PinnedHotelID=93231967&HadPinnedHotel=true&regionId=553248635976384612)

![Princess Heights Luxury Boutique Condo Hotel](https://images.trvl-media.com/lodging/1000000/570000/561400/561365/3eb207bd_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond Road No 156 Oyster Pond 

Fully refundableReserve now, pay when you stay

CA $398

CA $477 total

Mar 1 - Mar 2

includes taxes & fees

9.2/10 Wonderful! (1,000 reviews)

Very nice rooms, pool and workout room. Staff was very nice, friendly and accommodating.

Reviewed on Feb 10, 2026

[](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=561365&PinnedHotelID=561365&HadPinnedHotel=true&regionId=553248635976384612)

[See all 3,515 properties in Upper Prince's Quarter](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&regionId=553248635976384612)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### 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](https://images.trvl-media.com/place/6338950/46fc7f61-e6f6-4086-89f2-a96dde0b265c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Great Bay Beach

4/5(20 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. 

[](https://expedia.ca/Great-Bay-Beach-Philipsburg.d6338950.Vacation-Attraction)

![Fort Amsterdam which includes château or palace, a ruin and military items](https://images.trvl-media.com/place/502879/46df681c-cee4-49e7-9752-6835b75738b4.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Fort Amsterdam

5/5(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.

[](https://expedia.ca/Fort-Amsterdam-Philipsburg.d502879.Vacation-Attraction)

![Museum of Sint Maarten which includes art and interior views](https://images.trvl-media.com/place/502882/af4a98aa-fc42-4d6e-8fcd-2f2ca2c3ed45.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Museum of Sint Maarten

Discover where the native population originally came from and learn about major events in the island’s colonial, social and natural past.

[](https://expedia.ca/Museum-Of-Sint-Maarten-Downtown-Philipsburg.d502882.Vacation-Attraction)

### What to do in Upper Prince's Quarter

![High-Speed Ferry to St. Barths](https://mediaim.expedia.com/localexpert/176989/803f204c-e59b-47d1-9a40-1a59056c3ffb.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### High-Speed Ferry to St. Barths

CA $102

per adult

**80%** of travellers recommend

[](https://expedia.ca/things-to-do/high-speed-ferry-to-st-barths.a176989.activity-details)

![Panoramic view of vibrant St. Martin ](https://mediaim.expedia.com/localexpert/413439/1889a377-cdfa-4a6e-bdf7-cb7a36cef979.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Edge Ferry Tickets to St. Barts

CA $136

per adult

**84%** of travellers recommend

[](https://expedia.ca/things-to-do/edge-ferry-tickets-to-st-barts.a413439.activity-details)

![Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line](https://mediaim.expedia.com/localexpert/466226/f1e62739-a072-49a6-976a-ce1a3facd837.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

CA $184

per adult

**90%** of travellers recommend

[](https://expedia.ca/things-to-do/sky-explorer-flying-dutchman-schooner-sentry-hill-line.a466226.activity-details)

[See all activities in Upper Prince's Quarter](https://expedia.ca/things-to-do/search?rid=553248635976384612)

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