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.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Price was CA $2,543, price is now CA $1,714 per person
CA $1,714
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,010 reviews)
I genuinely want to personally Thank Jeremy and Nelson for their hospitality! They went above and beyond to make sure my wife and I were extremely comfortable. We felt completely safe and catered to with the care they showed us! I can’t forget what felt like our personal driver, Leticia! She’s absolutely amazing! I highly recommend requesting her if you need taxi services! You really made us feel at home! You guys are the best! Thank you so much! We can’t wait to come back and visit again! Much Love & Respect - Kela & Lany

Reviewed on Nov 7, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was CA $4,353, price is now CA $2,134 per person
CA $2,134
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,584 reviews)

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was CA $3,327, price is now CA $1,790 per person
CA $1,790
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
9/10 Wonderful! (2,129 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 on Nov 8, 2026

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was CA $3,009, price is now CA $1,759 per person
CA $1,759
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,001 reviews)
I loved the warm staff and the help they provided me during my stay

Reviewed on Nov 6, 2026

Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

5 out of 5
Price was CA $4,718, price is now CA $3,130 per person
CA $3,130
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
8.8/10 Excellent! (1,002 reviews)
Trip was wonderful… Rooms clean and nice. Food choices and quality good to excellent

Reviewed on Nov 8, 2026

Ready to book your vacation to Cole Bay?

 

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Cole Bay Hotel Deals

Port de Plaisance Resort, Trademark Collection by Wyndham

Port de Plaisance Resort, Trademark Collection by Wyndham

3.5 out of 5
155 Union Rd Cole Bay Sint Maarten
Fully refundableReserve now, pay when you stay
The price is CA $424 per night from Nov 9 to Nov 10
CA $424
CA $445 total
Nov 9 - Nov 10
includes taxes & fees
Port de Plaisance Resort, Trademark Collection by Wyndham
Carls Unique Inn

Carls Unique Inn

2 out of 5
18 Orange Grove Rd Cole Bay
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Nov 10 to Nov 11
CA $142
CA $175 total
Nov 10 - Nov 11
includes taxes & fees
Carls Unique Inn
Diamond Gem Residence

Diamond Gem Residence

3 out of 5
Peter John Rd Cole Bay Sint Maarten
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from Nov 20 to Nov 21
CA $118
CA $145 total
Nov 20 - Nov 21
includes taxes & fees
Diamond Gem Residence
See all 3,619 properties in Cole Bay
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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?
See properties

What to do in Cole Bay

Sand Dollar Snorkeling Adventure

Half Day Snorkeling Adventure

CA $92
per adult
100% of travellers recommend
Half Day Snorkeling Adventure
Tango Sunset Dinner Cruise

Tango Sunset Cruise with Caribbean Dinner & Open Bar

CA $108
per adult
94% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
Sky Explorer & 360 Views

Sky Explorer & 360 Views

CA $83
per adult
78% of travellers recommend
Sky Explorer & 360 Views
See all activities in Cole Bay

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 $1,714 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.