A white gate, a stone wall, and a pink building.
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Upper Prince's Quarter Vacations from $814

Book a Hotel + Flight or Car together to unlock savings

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.
  • Jan 8 - Jan 13

    Princess Heights Luxury Boutique Condo Hotel + Flight

    Oyster Pond
    5 nights
    3.5 star property
    9.2/10 - Wonderful (1,001 reviews)
    "I loved the warm staff and the help they provided me during my stay"
    Reviewed November 6, 2026
    Roundtrip • Boston (BOS) - Saint Martin (SXM)
    BOS - SXM • 1 stop SXM - BOS • 1 stop
    $1,639
    $814
    per traveler
    found 1 day ago
    Princess Heights Luxury Boutique Condo Hotel
  • Jan 8 - Jan 13

    The Villas at Simpson Bay Resort + Flight

    Pelican Key
    5 nights
    4.0 star property
    9.2/10 - Wonderful (1,606 reviews)
    Roundtrip • Boston (BOS) - Saint Martin (SXM)
    BOS - SXM • 1 stop SXM - BOS • 1 stop
    $3,246
    $1,570
    per traveler
    found 1 day ago
    The Villas at Simpson Bay Resort
  • Jan 21 - Jan 25

    Simpson Bay Resort, Marina & Spa + Flight

    Pelican Key
    4 nights
    4.0 star property
    9.0/10 - Wonderful (2,175 reviews)
    "Green flags: *gorgeous views *quiet while still near lots of restaurants/markets/nightlife *walkable beach *ample parking Pink flags: *disturbingly thin walls *paying for a deluxe balcony room w ocean view, then getting a random sealed room with a view to the buffet line RED FLAG: *the pregnant roach scurrying across the wall on our first night 😭"
    Reviewed November 8, 2026
    Roundtrip • Boston (BOS) - Saint Martin (SXM)
    BOS - SXM • Nonstop SXM - BOS • 1 stop
    $2,465
    $1,222
    per traveler
    found 1 day ago
    Simpson Bay Resort, Marina & Spa
  • Jan 8 - Jan 13

    The Morgan Resort Spa Village + Flight

    Simpson Bay
    5 nights
    4.0 star property
    9.0/10 - Wonderful (2,423 reviews)
    "Quiet, close to many restaurants and fun things to do. We had a driver- highly recommended"
    Reviewed November 7, 2026
    Roundtrip • Boston (BOS) - Saint Martin (SXM)
    BOS - SXM • 1 stop SXM - BOS • 1 stop
    $1,887
    $947
    per traveler
    found 1 day ago
    The Morgan Resort Spa Village
  • Jan 8 - Jan 13

    Panorama Residences at Monte Vista + Flight

    Point Blanche
    5 nights
    4.5 star property
    9.6/10 - Exceptional (105 reviews)
    "Super clean, beautiful location. Friendly staff. Safe place. Will book again"
    Reviewed October 24, 2026
    Roundtrip • Boston (BOS) - Saint Martin (SXM)
    BOS - SXM • 1 stop SXM - BOS • 1 stop
    $2,048
    $1,327
    per traveler
    found 1 day ago
    Panorama Residences at Monte Vista

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

What to do in Upper Prince's Quarter

Upper Prince's Quarter Hotel Deals

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.

Frequently Asked Questions

How much does an Upper Prince's Quarter vacation package cost?

You'll find cheap prices from $814 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.