Cole Bay Vacation Packages
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Your Cole Bay Vacation
The lively atmosphere and beaches are just the start of the things Cole Bay has going for it. Experience the best of this city the way you want with a personalized Cole Bay vacation package. Fill your free time with visits to Maho Beach, Marigot Market and Fort St. Louis, some of the attractions you should see during your trip to Cole Bay. Check out Expedia's extensive range of travel options and start organizing your ideal vacation to Cole Bay now.
Top Cole Bay Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
CA $1,332
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Philipsburg (SXM)
9.2/10 Wonderful! (1,000 reviews)
The staff is very friendly and accommodating. Beautiful views. The only thing I would ask is that water be restocked daily because it is easy to get dehydrated even if you buy your own water.
Reviewed on Sep 14, 2026
Simpson Bay Resort, Marina & Spa
Pelican Key
CA $1,796
per person
Dec 12 - Dec 19
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9/10 Wonderful! (1,987 reviews)
The beach and the views from our room was amazing! The beach has clear calm water. It was a fantastic time!
Reviewed on Sep 23, 2026
Panorama Residences at Monte Vista
Point Blanche
CA $1,986
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Philipsburg (SXM)
9.6/10 Exceptional! (93 reviews)
I a wonderful stay! The place was clean, comfortable, and exactly as described. The location was convenient, and everything we needed was provided. The host was friendly, responsive, and made the whole experience easy and enjoyable. We really appreciated the attention to detail and would definitely stay here again. Highly recommend!
Reviewed on Sep 23, 2026
Ready to book your vacation to Cole Bay?
Cole Bay Hotel Deals
Port de Plaisance Resort, Trademark Collection by Wyndham
155 Union Rd Cole Bay Sint Maarten
Fully refundableReserve now, pay when you stay
CA $197
CA $207 total
Sep 25 - Sep 26
includes taxes & fees
Carls Unique Inn
18 Orange Grove Rd Cole Bay
Fully refundableReserve now, pay when you stay
CA $103
CA $129 total
Sep 26 - Sep 27
includes taxes & fees
8.6/10 Excellent! (448 reviews)
"This place is really cheap for it's quality. The rooms are about the same quality"
Reviewed on Sep 6, 2026
Diamond Gem Residence
Peter John Rd Cole Bay Sint Maarten
Fully refundableReserve now, pay when you stay
CA $124
CA $151 total
Sep 26 - Sep 27
includes taxes & fees
9/10 Wonderful! (76 reviews)
"Notre hôte gracieux s'est montré chaleureux et accueillant. Il s'exprime en anglais et en français. D'autant plus qu'il est réactif quant aux requêtes. La propriété se situe à mi chemin entre les 2 parties de l'île, à proximité de magasins et restaurants, et l'aéroport. La sécurité est à la pointe ..."
Reviewed on Aug 29, 2026
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 Cole Bay attractions
Indigo Beach
8.0/10 (23 reviews)
Why not spend a lazy afternoon at Indigo Beach during your trip to Cole Bay?
Burgeaux Bay Beach
7.6/10 (9 reviews)
Why not spend a lazy afternoon at Burgeaux Bay Beach during your trip to Cole Bay?
Seaside Nature Park
8.0/10 (14 reviews)
Explore the lovely green spaces of Seaside Nature Park and enjoy the boating in Cole Bay. Stroll along the seaside or discover the beautiful sunsets in this romantic area.
What to do in Cole Bay
Half Day Snorkeling Adventure
CA $90
per adult
100% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
CA $106
per adult
94% of travellers recommend
Mambo Catamaran Cruise to Rendezvous Bay Anguilla with Lunch
CA $187
per adult
86% of travellers recommend
Frequently asked questions
How much does a Cole Bay vacation package cost?
You can snap up a vacation package to this popular destination from CA $1,332 on Expedia. However, how much your vacation to Cole Bay costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Cole Bay?
September, October and November are the best times to search for cheap Cole Bay vacation packages. Opting to travel in quieter periods means you can typically find lower prices on hotels and flights.
How many days is enough for Cole Bay?
Allow at least 4 days for your Cole Bay vacation to really immerse yourself in all that makes this destination unique. Explore key neighbourhoods, including Pelican Key and Upper Prince's Quarter. Then check out top attractions like Great Bay Beach and Grand Case Beach. With a good itinerary, you can keep busy with room for some me-time too. Want to go beyond Cole Bay? Consider fitting in an excursion or two.
How to find the best Cole Bay package deals?
Begin your search for a Cole Bay package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Cole Bay package deal right away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Cole Bay escape underway.
Is it cheaper to book a Cole Bay vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and hotels individually. Better still, you can tailor your Cole Bay getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Cole Bay?
Land fantastic discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Cole Bay trip.
How to plan a trip to Cole Bay?
- Choose when to travel: Check your diary and get packing. Your preferred time of year and the type of activities on offer will also help you decide when to visit Cole Bay.
- Set your budget: Factor in costs like transportation, flights and meals when calculating how much to put aside for your trip to Cole Bay. Then, pick a property that matches your budget, whether that's an economical option or a more luxurious retreat.
- Set the duration of your trip: Start by compiling a list of the activities and sights you'd like to get to in Cole Bay. Then, estimate how long you'll need at each, as well as any travel time.
- Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customized Cole Bay vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
