Little Bay Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Your Little Bay Vacation
The stress-free way to experience this exciting city is with a customized Little Bay vacation package. Stay in the neighborhood of Upper Princes Quarter, which is good for shopping, coastal beaches and nature or choose someplace else — our package deals are all about you. Make your trip to Little Bay even more exciting by including some sightseeing. Little Bay Beach, Sint Maarten Park and Guana Bay Beach are some of the major attractions you'll want to explore. Your ideal Little Bay vacation is just clicks away. Search hotels, airfares and more on Expedia for an adventure that's tailored to suit your style.
Top Little Bay Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Villas at Simpson Bay Resort
Pelican Key
CA $1,617
per person
Oct 9 - Oct 16
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,484 reviews)
Very nice property in a excellent location in Simpson Bay. Rooms are large, good kitchen set up in the rooms, excellent restaurants and great people. I'd certainly stay again with my only two complaints being that the gym carries a $6 per use cost (I was under the impression it was included in the room cost - $6 is cheap but a little annoying that it's not included) and the really awesome bar right on the water closes a little before sunset. It would be really fun if that bar stayed open an hour after sunset.
Reviewed on Aug 7, 2026
Sonesta Ocean Point All Inclusive, Adults Only Resort
CA $4,249
per person
Oct 9 - Oct 16
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
8.8/10 Excellent! (1,003 reviews)
Everyone was so friendly and accommodating. My husband and I will definitely be returning!
Reviewed on Aug 8, 2026
Ready to book your vacation to Little Bay?
Little Bay Hotel Deals
Divi Little Bay Beach Resort
Little Bay Road Philipsburg
Fully refundableReserve now, pay when you stay
CA $228
CA $301 total
Sep 8 - Sep 9
includes taxes & fees
Oceans at Divi Little Bay
Little Bay Road Philipsburg St. Maarten
Fully refundableReserve now, pay when you stay
CA $299
CA $390 total
Sep 8 - Sep 9
includes taxes & fees
8.2/10 Very good! (525 reviews)
"N/A"
Reviewed on Aug 8, 2026
Belair Beach Hotel
Little Bay Philipsburg
CA $286
CA $346 total
Aug 15 - Aug 16
includes taxes & fees
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.
Stay near popular Little Bay attractions
Fort Amsterdam
8.8/10 (245 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.
What to do in Little Bay
Half Day Snorkeling Adventure
CA $91
per adult
100% of travellers recommend
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
CA $190
per adult
90% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
CA $120
per adult
94% of travellers recommend
Frequently asked questions
How much does a Little Bay vacation package cost?
Offering great value package deals from CA $1,061 on Expedia, you'll be surprised at how little a vacation to Little Bay costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Little Bay?
You can typically find lower prices and greater availability in September, October and November. Take a look at our cheap Little Bay vacation packages and you could score some great off-season deals.
How many days is enough for Little Bay?
With around 5 days, you'll have plenty of time to enjoy popular neighbourhoods such as Upper Prince's Quarter and Madame's Estate during your Little Bay vacation. Be sure to also add Sint Maarten Park and Guana Bay Beach to your must-see list. Searching for more adventures? Consider venturing outside of Little Bay on day trips and tours.
How to find the best Little Bay package deals?
Use Expedia's filters to help you find some of the best Little Bay package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Little Bay package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Little Bay vacation as a package?
You can enjoy significant savings on your next Little Bay break by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to browse the best hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Little Bay?
If you've got your Little Bay travel dates locked in, book early to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are great for quick escapes.
How to plan a trip to Little Bay?
- Choose your dates: What you plan to do in Little Bay and your preferred season will help you decide when to get away.
- Budget wisely: On top of the price of your stay, you'll need to consider other expenses too. These include transportation, food and flights. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Little Bay.
- Decide your trip length: Consider how long you'd like to spend discovering Little Bay. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
- Bundle your accommodations and airfare: Once you've settled on your trip dates and duration, book the right Little Bay vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
