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.
Holland House Beach Hotel

Holland House Beach Hotel

Downtown Philipsburg
CA $1,435
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,000 reviews)
The View🏖️

Reviewed on Sep 1, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Pelican Key
CA $1,512
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,981 reviews)
Everything was wonderful! However, I did not like that a part of the resort

Reviewed on Sep 2, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
CA $1,505
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,519 reviews)
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

CA $1,888
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8/10 Very good! (3,182 reviews)
My stay at Sonesta All-Inclusive St. Maarten was an okay experience overall, but unfortunately, there were two incidents that significantly affected my impression of the resort. First, and most concerning, someone actually opened the door to my room while I was lying in bed. I immediately went downstairs and reported the incident to the staff. What was even more disappointing was the response from the person in charge of security. I was basically told to go back to my room and that they would review the security cameras in the morning to determine who had opened my door. Seriously? Someone had just gained access to my room while I was inside, and I was expected to simply return to the room and wait until the next morning for answers. I needed to know immediately who had access to my room and whether I was safe staying there. I was actually the one who had to suggest that they contact the other staff members working that evening to find out who had entered my room. For an all-inclusive resort, I expected a much more immediate and professional response to such a serious security concern. The second issue involved an ATV excursion that my wife and I paid for. We specifically paid for two ATVs so that we could each ride our own. Before the excursion even left the resort, another guest was involved in an accident. Afterward, my ATV was taken away and I was told that I had to ride together with my wife, even though we had already paid for two separate ATVs .

Reviewed on Sep 3, 2026

Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

Point Blanche
CA $1,820
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.6/10 Exceptional! (92 reviews)
The property was well maintained. The room was stunning and the views were spectacular! Ms Nicky referred me to a driver who was prompt and reliable. I would 100% recommend this property to anyone looking to vacay in St Maarten!!

Reviewed on Aug 27, 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

155 Union Rd Cole Bay Sint Maarten
Fully refundableReserve now, pay when you stay
CA $235
CA $247 total
Sep 8 - Sep 9
includes taxes & fees
7.6/10 Good! (776 reviews)
"The staff and hotel room view was amazing, bathroom a bit small though."

Reviewed on Aug 26, 2026

Port de Plaisance Resort, Trademark Collection by Wyndham
Diamond Gem Residence

Diamond Gem Residence

Peter John Rd Cole Bay Sint Maarten
Fully refundableReserve now, pay when you stay
CA $134
CA $161 total
Sep 4 - Sep 5
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

Diamond Gem Residence
Carls Unique Inn

Carls Unique Inn

18 Orange Grove Rd Cole Bay
Fully refundableReserve now, pay when you stay
CA $102
CA $127 total
Sep 8 - Sep 9
includes taxes & fees
8.6/10 Excellent! (446 reviews)
"The property was very nice and the rooms were very modern and clean. The breakfast was really good and the location of the hotel is really convenient as well."

Reviewed on Aug 27, 2026

Carls Unique Inn
See all 3,633 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.

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

Burgeaux Bay Beach

7.6/10 (9 reviews)
Why not spend a lazy afternoon at Burgeaux Bay Beach during your trip to Cay Bay?
See properties

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 beautiful beaches or discover the beautiful sunsets in this family-friendly area.
See properties

What to do in Cole Bay

Sand Dollar Snorkeling Adventure

Half Day Snorkeling Adventure

CA $90
per adult
100% of travellers recommend
Half Day Snorkeling Adventure
Tango Sunset Dinner Cruise

Tango Sunset Cruise with Caribbean Dinner & Open Bar

CA $106
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 $112
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 $1,435 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.