Cole Bay Vacations from $706

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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.

The Latest Cole Bay vacation packages

Price found within the past 48 hours. Click for updated prices.
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Price was $1,014, price is now $706 per person
$706
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,003 reviews)
Wonderful stay. Only issue is the WiFi for the TV wasn’t stable but all else was amazing!

Reviewed on Aug 27, 2025

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Save 100% on your flight
Price was $2,669, price is now $1,492 per person
$1,492
per person
Nov 22 - Nov 29
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (1,291 reviews)
I have stayed at Simpson bay a few times. This time the room felt like a cave. Dark and lonely at the end of the building. The hotel is clean and staff very nice though. Did not have a chance to use the pool this time, but it was always crowded, which means the place is popular. Overall I enjoyed the stay.

Reviewed on Aug 31, 2025

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
Price was $1,299, price is now $750 per person
$750
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,227 reviews)
Family friendly and staff are exceptional.

Reviewed on Aug 31, 2025

Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Price was $1,053, price is now $736 per person
$736
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
8.6/10 Excellent! (922 reviews)
Everything was very nice. The free breakfast was very limited- contintental breakfast. The hotel shuttle was a local taxi & cost $35. We needed an accommodation for our big anniv. celebration but nobody seemed to help us nor provide for us, which was a bottle of cider instead of alcohol. That was supposed to be gà

Reviewed on Aug 25, 2025

Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was $1,304, price is now $954 per person
$954
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
8.6/10 Excellent! (464 reviews)
Nice having semi-private pool. All of the staff very friendly and helpful. Including at L'Astrolabe for breakfast and dinner.

Reviewed on Jun 13, 2025

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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

Discover the most popular places to visit in Cole Bay

Indigo Beach

Why not spend a lazy afternoon at Indigo Beach during your trip to Cole Bay?

Indigo Beach

Seaside Nature Park

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.

Seaside Nature Park

What to do in Cole Bay

St. Maarten Maho Beach Tour

St. Maarten Maho Beach Tour

$40
per adult
80% of travellers recommend
St. Maarten Maho Beach Tour
Boomerang’s Best of Anguilla: Swim with Turtles Adventure

Boomerang’s Best of Anguilla: Swim with Turtles Adventure

$170
per adult
100% of travellers recommend
Boomerang’s Best of Anguilla: Swim with Turtles Adventure
Zipline Experience: Sentry hill Zip & Flying Dutchman

Zipline Experience: Sentry hill Zip & Flying Dutchman

$110
per adult
Zipline Experience: Sentry hill Zip & Flying Dutchman
See all activities in Cole Bay

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
$110 nightly
The price is $115 total per night from Sep 1 to Sep 2
$115 total
Sep 1 - Sep 2
Total with taxes and fees
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
$93 nightly
The price is $98 total per night from Sep 2 to Sep 3
$98 total
Sep 2 - Sep 3
Total with taxes and fees
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
$111 nightly
The price is $116 total per night from Sep 2 to Sep 3
$116 total
Sep 2 - Sep 3
Total with taxes and fees
Carls Unique Inn
See all 3,596 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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Frequently asked questions

How much does a Cole Bay vacation package cost?
You'll find cheap prices from $706 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 generally find reduced prices and greater availability in April, July and December. Check out our cheap Cole Bay vacation packages and you could score some great off-season discounts.
How many days is enough for Cole Bay?
With a well-organized itinerary, you can easily visit the most popular Cole Bay sights in a few days. But if you'd like to discover lesser-known spots or go on day trips, consider booking your Cole Bay vacation for longer.
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 the right time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to travel to Cole Bay.
  2. Budget wisely: Besides the price of your hotel, you'll need to factor in other expenses. These include flights, food and transportation. Also, put aside some extra funds for unexpected costs that may arise during your trip to Cole Bay.
  3. Use our trip planning tool to discover Cole Bay: Research every part of your trip to Cole Bay with this comprehensive planner. Invite friends or family to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Work out your trip length: Think about how long you want to spend discovering Cole Bay. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  5. Bundle your airfare and accommodations: After you've nailed down your travel dates and duration, book the ideal Cole Bay vacation package for you.
  6. Add on experiences and excursions: Take a look at our dedicated travel guide to find some incredible things to do in Cole Bay. Book tickets or make reservations in advance to save time and avoid the stress of searching for activities once you arrive.

Does Expedia offer Book Now, Pay Later Cole Bay vacation packages?
Set off on your perfect trip to Cole Bay with help from Expedia's Book Now, Pay Later vacations. No need to save up or wait until your next paycheck — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily budget for your trip and snap up bargains before they disappear.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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