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

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was CA $2,231, price is now CA $1,436 per person
CA $1,436
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,001 reviews)
This is my 2nd time staying at the property. The property & room are clean, I did not use the pool, but I could see it from my ocean view room. It does not appear that any other guest used it either. The breakfast was nothing much... my 1st stay we were given ham & cheese croissants, this time just plain ( I assume a budgeting issue). The Ham and cheese croissants is much preferred. Also came with coffee, creamer, chocolate croissant & orange juice (not fresh). The kitchenette was in great condition and super clean.

Reviewed on Jul 8, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was CA $4,204, price is now CA $1,965 per person
CA $1,965
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,442 reviews)
I loved everything about it. The comfort felt like home. No complaints

Reviewed on Jul 11, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was CA $3,507, price is now CA $1,744 per person
CA $1,744
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,837 reviews)
Beautiful resort, I will definitely recommend it, it can use a little maintenance in the rooms, maybe a little remodeling...very clean, I spoke with one of the supervisors (managers) and he was incredible, very pleasant and immediately try to see how he can fix things and make my stay better... The resort is so big that some buildings are too far from the lobby but the view is amazing I didn't even care no to be right next to the water... I will definitely comeback..

Reviewed on Jul 11, 2026

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was CA $4,162, price is now CA $2,773 per person
CA $2,773
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (2,255 reviews)
Staff very helpful and very nice

Reviewed on Jul 11, 2026

Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was CA $2,629, price is now CA $1,780 per person
CA $1,780
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.6/10 Excellent! (533 reviews)
Most of all, the peace and quiet here is fantastic and very close to the beach and restaurants.

Reviewed on Jul 6, 2026

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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 $255 per night from Jul 12 to Jul 13
CA $255
CA $268 total
Jul 12 - Jul 13
includes taxes & fees
7.6/10 Good! (760 reviews)
"The rooms are well kept and the BBQ restaurant is great"

Reviewed on Jul 11, 2026

Port de Plaisance Resort, Trademark Collection by Wyndham
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 $135 per night from Aug 8 to Aug 9
CA $135
CA $162 total
Aug 8 - Aug 9
includes taxes & fees
9/10 Wonderful! (75 reviews)
"The room was clean, comfortable and had all the amenities needed. The owner was very accommodating with my request for a noon check out which was greatly appreciated due to my flight departure. The place is located close to restaurants and grocery store."

Reviewed on Jun 20, 2026

Diamond Gem Residence
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 $118 per night from Jul 19 to Jul 20
CA $118
CA $148 total
Jul 19 - Jul 20
includes taxes & fees
8.6/10 Excellent! (438 reviews)
"Parking free breakfast"

Reviewed on Jul 6, 2026

Carls Unique Inn
See all 3,608 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.
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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 $121
per adult
94% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

CA $115
per adult
80% of travellers recommend
High-Speed Ferry to St. Barths
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 $1,436 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.