Cole Bay Vacations from ￥77,171

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The Latest Cole Bay Vacation Packages

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
Save 100% on your flight
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Philipsburg (SXM)
8.6/10 Excellent! (906 reviews)
Needs more food options, and updates to the property.

Reviewed on Aug 3, 2025

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Save 100% on your flight
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Philipsburg (SXM)
9.2/10 Wonderful! (946 reviews)
Wonderful customer service

Reviewed on Aug 3, 2025

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Philipsburg (SXM)
9.2/10 Wonderful! (1,218 reviews)
Lovely had a great time

Reviewed on Aug 4, 2025

Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

4 out of 5
Save 100% on your flight
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Philipsburg (SXM)
9/10 Wonderful! (1,062 reviews)
We had such a great time during our stay! From the moment we arrived, the front desk staff made us feel so welcome—friendly, professional, and incredibly helpful. The food was absolutely amazing, with every meal exceeding our expectations. The location couldn’t have been more perfect—convenient, scenic, and close to everything we needed. Every staff member we interacted with was warm and genuinely friendly, which made the entire experience even better. We truly can’t wait to come back!

Reviewed on Aug 5, 2025

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Save 100% on your flight
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Philipsburg (SXM)
9.2/10 Wonderful! (1,000 reviews)
Holland House was a good stay and great location.I traveled solo and everyone was nice and friendly. I really appreciated how helpful the two lady receptionist at the front were and Forbes who worked on the beach and at the restaurant. Room was nice.My only suggestion is that the cleaning staff take time to look over certain details when cleaning the rooms. Other than that I enjoyed myself.

Reviewed on Aug 4, 2025

Where to stay in Cole Bay

Find the best Cole Bay areas and neighborhoods for the activities you enjoy most. Learn more about Cole Bay
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Indigo Bay

1 out of top 10 points of interest in this area

While Indigo Bay isn't home to many top sights, Little Bay Beach and Indigo Beach are some notable places to visit nearby.

Find hotels in Indigo Bay

Find the Best Cole Bay Vacation Packages

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 ￥16,089 per night from Aug 11 to Aug 12
￥16,089
￥16,893 total
Aug 11 - Aug 12
includes taxes & fees
7.6/10 Good! (644 reviews)
"Everything was awesome. Quiet and peaceful. Only let down was the pool. Needs some repairs"

Reviewed on Jul 14, 2025

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 ￥12,936 per night from Aug 24 to Aug 25
￥12,936
￥15,779 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (59 reviews)
"A very good option due to price, location, and amenities. Owner is very friendly. Would definitely stay there again."

Reviewed on Jul 12, 2025

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 ￥13,985 per night from Aug 8 to Aug 9
￥13,985
￥17,062 total
Aug 8 - Aug 9
includes taxes & fees
8.6/10 Excellent! (346 reviews)
"Great place. Very convenient."

Reviewed on Jul 27, 2025

Carls Unique Inn
See all 3,587 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.

What to do in Cole Bay

Tango Sunset Dinner Cruise

Tango Sunset Cruise with Caribbean Dinner & Open Bar

￥12,554
per adult
94% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
Lunch at Meads BAy

Ultimate Prickly Pear and Anguilla Experience

￥22,006
per adult
82% of travellers recommend
Ultimate Prickly Pear and Anguilla Experience
High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

￥11,077
per adult
76% 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'll find cheap prices from ￥77,171 on Expedia for your Cole Bay escape. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Cole Bay costs.
What are the cheapest months to go to Cole Bay?
You can usually find lower prices and greater availability in September, October and November. Explore our cheap Cole Bay vacation packages and you could land some excellent off-season deals.
How many days is enough for Cole Bay?
The ideal length of your Cole Bay vacation depends on what you'd like to see. Typically, a handful of days to a week will give you time to visit all the major attractions and discover some hidden spots along the way.
How to find the best Cole Bay package deals?
Finding a cheap Cole Bay package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply a couple of filters and see what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to view the most economical Cole Bay package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Cole Bay vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Cole Bay vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Cole Bay?
If you're planning a spontaneous Cole Bay vacation, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to Cole Bay?

  1. Choose your travel dates: What you'd like to do in Cole Bay and your favorite season will help you decide when to get away.
  2. Budget wisely: As well as the cost of your accommodations, you'll need to factor in other expenses. These include transportation, food and flights. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Cole Bay.
  3. Decide how long to go away for: Now that you know more about Cole Bay, you can work out the perfect length of your vacation. Put together a draft itinerary and give yourself enough time for all the things you want to do.
  4. Bundle your accommodations and airfare: Once you've nailed down your dates and duration, book the ideal Cole 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.