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Upper Prince's Quarter flight + hotel packages

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
per person
Jun. 13 - Jun. 20
Roundtrip non-stop flight included
Montreal (YUL) to Philipsburg (SXM)
Stay at this 4-star beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby. Discover genuine guest reviews for The Villas at Simpson Bay Resort along with the latest prices and availability – book now.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
per person
Jun. 13 - Jun. 20
Roundtrip non-stop flight included
Montreal (YUL) to Philipsburg (SXM)
Stay at this 4-star beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby. Discover genuine guest reviews for Simpson Bay Resort, Marina & Spa, in Pelican Key neighborhood, along with the latest prices and availability – book now.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
per person
Jun. 13 - Jun. 20
Roundtrip non-stop flight included
Montreal (YUL) to Philipsburg (SXM)
Stay at this 3.5-star family-friendly hotel in Oyster Pond. Enjoy free WiFi, free parking, and breakfast. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Orient Bay Beach and Dawn Beach are located nearby. Discover genuine guest reviews for Princess Heights Luxury Boutique Condo Hotel, in Oyster Pond neighborhood, along with the latest prices and availability – book now.
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
per person
Jun. 13 - Jun. 20
Roundtrip non-stop flight included
Montreal (YUL) to Philipsburg (SXM)
Stay at this 4-star beach hotel in Orient Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Orient Bay Beach and Green Cay are located nearby. Discover genuine guest reviews for La Playa Orient Bay along with the latest prices and availability – book now.
Esmeralda Resort

Esmeralda Resort

4 out of 5
Save 100% on your flight
per person
May 26 - Jun. 2
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
Stay at this 4-star beach hotel in Orient Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Orient Bay Beach and Mont Vernon are located nearby. Discover genuine guest reviews for Esmeralda Resort along with the latest prices and availability – book now.
Prices and availability subject to change. Additional terms may apply.

Top Upper Prince's Quarter hotels deals

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 $341 per night
CA $341
per night
May 1 - May 2
Stay at this 5-star luxury hotel in Oyster Pond. Enjoy free WiFi, free parking, and 3 restaurants. Popular attractions Orient Bay Beach and Dawn Beach are located nearby. Discover genuine guest reviews for JW Marriott St. Maarten Beach Resort & Spa, in Oyster Pond neighborhood, along with the latest prices and availability – book now.
Pool
Spa
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
10 Emerald Merit Rd, Oyster Pond
Free cancellation
Reserve now, pay when you stay
The price is CA $201 per night
CA $201
per night
May 4 - May 5
Stay at this 4-star beach resort in Oyster Pond. Enjoy free WiFi, 2 restaurants, and a marina. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Orient Bay Beach and Oyster Bay Marina are located nearby. Discover genuine guest reviews for Oyster Bay Beach Resort, in Oyster Pond neighborhood, along with the latest prices and availability – book now.
Hot tub
Pool
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
Free cancellation
Reserve now, pay when you stay
The price is CA $217 per night
CA $217
per night
May 1 - May 2
Stay at this 3.5-star family-friendly hotel in Oyster Pond. Enjoy free WiFi, free parking, and breakfast. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Orient Bay Beach and Dawn Beach are located nearby. Discover genuine guest reviews for Princess Heights Luxury Boutique Condo Hotel, in Oyster Pond neighborhood, along with the latest prices and availability – book now.
Pet-friendly
Pool
Dawn Beach Club Resort Sint Maarten

Dawn Beach Club Resort Sint Maarten

4 out of 5
144 Oyster Pond Rd, Oyster Pond, Sint Maarten
Free cancellation
Reserve now, pay when you stay
The price is CA $871 per night
CA $871
per night
May 20 - May 21
Stay at this 4-star beach condo in Oyster Pond. Enjoy free parking, 2 restaurants, and a beach locale. Popular attractions Orient Bay Beach and Dawn Beach are located nearby. Discover genuine guest reviews for Dawn Beach Club Resort Sint Maarten, in Oyster Pond neighborhood, along with the latest prices and availability – book now.
Pool
Breakfast available
Luxury Villa w Spectacular Ocean Views, private pool/Hottub, Walk to Beach

Luxury Villa w Spectacular Ocean Views, private pool/Hottub, Walk to Beach

Get rates
Stay at this beach villa in Oyster Pond. Enjoy free WiFi, private pools, and a beach locale. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Orient Bay Beach and Dawn Beach are located nearby. Discover genuine guest reviews for Luxury Villa w Spectacular Ocean Views, private pool/Hottub, Walk to Beach, in Oyster Pond neighborhood, along with the latest prices and availability – book now.
Hot tub
Pet-friendly
LITERALLY OCEANFRONT VILLA ALABASTER, DAWN BEACH w private pool ~ Owners' site

LITERALLY OCEANFRONT VILLA ALABASTER, DAWN BEACH w private pool ~ Owners' site

Get rates
Stay at this beach villa in Oyster Pond. Enjoy free WiFi, private pools, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Orient Bay Beach and Oyster Bay Marina are located nearby. Discover genuine guest reviews for LITERALLY OCEANFRONT VILLA ALABASTER, DAWN BEACH w private pool ~ Owners' site , in Oyster Pond neighborhood, along with the latest prices and availability – book now.
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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.

Popular places to visit

Image for Great Bay Beach

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.

Great Bay Beach
Image for Guana Bay Beach

Guana Bay Beach

5/5(2 reviews)

If a restful vacation is part of your travel plans, Guana Bay Beach might be the perfect place to seek out during your trip to Upper Prince's Quarter.

Guana Bay Beach
Image for Philipsburg Boardwalk

Philipsburg Boardwalk

Philipsburg Boardwalk is just one of the places to see in Philipsburg, so why not enjoy the other things to explore during your travels? Stroll along the area's beaches or simply enjoy its restaurants.

Philipsburg Boardwalk

Frequently asked questions

How much are vacation packages to Upper Prince's Quarter?
Enjoy a memorable experience in Upper Prince’s Quarter with a vacation package starting at CA $1,594. Locking in your flights, tours and hotels with Travelocity is easy. On top of that, our package deals will leave you with more money in your pocket for plenty of fun activities.
Where can I get the best vacation package deals for Upper Prince's Quarter?
You can’t beat Travelocity when it comes to crafting your Upper Prince’s Quarter package deal. There are at least 400 air carriers and 665,000 worldwide properties to choose from. Secure your trip now and get ready to cross another amazing place off your must-visit list.
Why should I book my Upper Prince's Quarter vacation package via Travelocity?
Because life is one amazing journey, and we’ve got everything you need to help you on your way. With our high-quality service and Price Match Guarantee, you can organize your trip with confidence. What’s more, you can sleep easy on the road knowing we’ve got your back with our 24/7 customer support.
Can I save money on my Upper Prince's Quarter car rental if I book it with hotels and flights?
Absolutely. And our Upper Prince’s Quarter vacation packages are the ideal way to do it. With only a few clicks you can save cash as well as time by combining your bookings. Collect the keys to your rental car then set your own course. Need to fill your itinerary? Throw some tours or experiences into your package and save on those too.
What is the best time of year to go to Upper Prince's Quarter?
If you love to wander wisely, is a great time to do it. That’s when you’ll find hotel rates are at their most affordable. In contrast, prices skyrocket around . are the most popular months to visit Upper Prince’s Quarter, so expect long lines for major tourist sites. Prefer to avoid the busy season? You’ll find fewer visitors during .
What is there to do in Upper Prince's Quarter?
While wandering about Upper Prince’s Quarter, check out Dawn Beach and Museum of Sint Maarten. You won’t be bored here!
Where should I stay when visiting Upper Prince's Quarter?
Stay at the Oyster Bay Beach Resort (4.0 stars) or the Coral Beach Club Villas & Marina (4.0 stars). These plush options in Upper Prince’s Quarter go beyond clean rooms and cozy beds to offer you an outstanding travel experience.
Can I go on vacation to Upper Prince's Quarter at this time?
Don’t fly off to Upper Prince’s Quarter without up-to-date facts about quarantine policies and travel restrictions. Travelocity’s Covid-19 Travel Advisor can fill in the blanks. Our local experts have pulled together all the info you need to make your vacation plans as stress-free as possible.