A white gate, a stone wall, and a pink building.
Photo by Third Avenue Lady
Open Photo by Third Avenue Lady

Upper Prince's Quarter Vacations from $817

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

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

The Latest Upper Prince's Quarter Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Oct 10 - Oct 14

    Simpson Bay Resort, Marina & Spa + Flight

    Pelican Key
    4 nights
    4.0 star property
    9.0/10 - Wonderful (1,908 reviews)
    "The resort is cute and close to everything, the shuttle was also a great help. The room is a little old, but I definitely recommend it."
    Reviewed July 27, 2026
    Roundtrip New York (EWR) - Saint Martin (SXM)
    EWR - SXM1 stop SXM - EWR1 stop
    Save 100% on your flight
    $1,695
    $817
    per traveler
    found 1 day ago
    Simpson Bay Resort, Marina & Spa
  • Oct 10 - Oct 14

    The Villas at Simpson Bay Resort + Flight

    Pelican Key
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,489 reviews)
    "Room was very nice with a great view (junior suite - oceanfront). The bathroom however needs a renovation (room PM203B). It is dated. The bath tap was hanging off the wall and the old & worn out plug/drain wasn’t the most pleasing to the eye. Plenty pools to choose from for kids or adults and great access to the beach. Conveniently located shop within surroundings which has all the supplies you could need. Staff were mainly friendly however there were a few who came across very..."
    Reviewed July 28, 2026
    Roundtrip New York (EWR) - Saint Martin (SXM)
    EWR - SXM1 stop SXM - EWR1 stop
    $2,068
    $921
    per traveler
    found 1 day ago
    The Villas at Simpson Bay Resort
  • Oct 11 - Oct 16

    The Morgan Resort Spa Village + Flight

    Simpson Bay
    5 nights
    4.0 star property
    9.0/10 - Wonderful (2,315 reviews)
    Roundtrip New York (EWR) - Saint Martin (SXM)
    EWR - SXM1 stop SXM - EWR1 stop
    Save 100% on your flight
    $1,821
    $1,146
    per traveler
    found 1 day ago
    The Morgan Resort Spa Village
  • Oct 11 - Oct 16

    Princess Heights Luxury Boutique Condo Hotel + Flight

    Oyster Pond
    5 nights
    3.5 star property
    9.2/10 - Wonderful (1,004 reviews)
    "L’hôtel est magnifique, avec une vue imprenable sur l’océan d’un côté et sur les montagnes de l’autre. Nous avions un appartement avec deux chambres, ce qui était parfait pour une famille de deux adultes et deux enfants. Chaque chambre avait sa propre salle de bain et il y avait deux balcons face à la mer. L’air climatisé était très efficace. L’hôtel était en parfait état et propre. Le gym était un bel atout pour les entraînements matinaux. La piscine était très agréable. Nous avons croisé des..."
    Reviewed July 23, 2026
    Roundtrip New York (EWR) - Saint Martin (SXM)
    EWR - SXM1 stop SXM - EWR1 stop
    Save 100% on your flight
    $1,235
    $818
    per traveler
    found 1 day ago
    Princess Heights Luxury Boutique Condo Hotel
  • Oct 11 - Oct 16

    Esmeralda Resort + Flight

    Orient Bay
    5 nights
    4.0 star property
    8.6/10 - Excellent (537 reviews)
    Roundtrip New York (EWR) - Saint Martin (SXM)
    EWR - SXM1 stop SXM - EWR1 stop
    $1,210
    $848
    per traveler
    found 1 day ago
    Esmeralda Resort

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 $817 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.