Oyster Pond Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in Oyster Pond

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 $1,691, price is now CA $1,139 per person
CA $1,139
per person
Oct 3 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.8/10 Excellent! (1,021 reviews)
No beach for an oceanfront trip. I couldn’t be more disappointed.

Reviewed on Jul 20, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was CA $2,765, price is now CA $1,244 per person
CA $1,244
per person
Oct 3 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,887 reviews)
The rooms were very clean, the lobby is beautiful and clean. The washcloths and sheets were scratchy though. If you stay in the B building, the hills are very steep to walk up to the building. The entire complex is huge and it takes a bit of time to figure out how to walk to places. there are numerous pools and bars. most of the staff were nice but some staff seemed uninterested and were just doing their jobs. The mexican restaurant was very good. The beach was great and the water was perfect. there is some snorkling right off the beach.

Reviewed on Jul 21, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was CA $3,417, price is now CA $1,557 per person
CA $1,557
per person
Oct 9 - Oct 14
found 18 hours ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,473 reviews)
Every was brilliant, ideal location for all restaurants, beach, bars and nightlife. I was only a little disappointed thwt we had to change rooms on the last night. The change only was seamless. The food was very good too. Enjoyed my trip to town, the was organised by a local jewellery store, should have been warned ahead of time as they are keen for you to buy things on there shop which took up a bit of the time we had. Apart from that excellent hotel.

Reviewed on Jul 21, 2026

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was CA $3,346, price is now CA $2,207 per person
CA $2,207
per person
Oct 3 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (2,287 reviews)

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Price was CA $2,175, price is now CA $1,524 per person
CA $1,524
per person
Oct 3 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,007 reviews)

Oyster Pond Hotel Deals

Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
10 Emerald Merit Rd Oyster Pond
Fully refundableReserve now, pay when you stay
The price is CA $231 per night from Aug 17 to Aug 18
CA $231
CA $277 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (1,017 reviews)
"No beach for an oceanfront trip. I couldn’t be more disappointed."

Reviewed on Jul 20, 2026

Oyster Bay Beach Resort
JW Marriott St. Maarten Beach Resort & Spa

JW Marriott St. Maarten Beach Resort & Spa

5 out of 5
144 Oyster Pond Resort Oyster Pond Sint Maarten
The price is CA $503 per night from Aug 17 to Aug 18
CA $503
CA $649 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (339 reviews)
"The property was kept in excellent condition. Staff was so welcoming and so helpful which made our stay even more enjoyable. The hotel we found was far away from most popular places to visit which is what we didn't like about the place. You definitely need a car to drive to places. The restaurants ..."

Reviewed on Jul 21, 2026

JW Marriott St. Maarten Beach Resort & Spa
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond Road No 156 Oyster Pond
Fully refundableReserve now, pay when you stay
The price is CA $321 per night from Aug 1 to Aug 2
CA $321
CA $385 total
Aug 1 - Aug 2
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"We truly enjoyed our stay at Princess Heights. The hotel was very clean and well kept. We had a broken microwave and when we called about it, it was switched out the next day. It was sometimes difficult to get in contact with the staff being that they usually left right after 5pm. I also would recommend, ..."

Reviewed on Jul 15, 2026

Princess Heights Luxury Boutique Condo Hotel
See all 7,822 properties in Oyster Pond
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 an Oyster Pond vacation package cost?
Starting from as low as CA $1,139, you can tailor make your Oyster Pond package the way you want. Simply combine hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Oyster Pond?
Bundle your hotels and flights with Expedia to save big on your next big adventure. With more than 550 air carriers and 1,000,000 properties across the globe, your Oyster Pond vacation package can be tailored exactly to suit your budget. With all those extra dollars, why not include a few interesting activities and tours? It's an easy way to unlock even more bargains. Your dream getaway to Oyster Pond is closer than you thought!
Where should I stay in Oyster Pond?
With so much to explore in Oyster Pond, it makes sense to lock in a hotel near its attractions. Dawn Beach, Oyster Bay Marina and Coralita Beach are some fascinating ones to put on your to-do list.
What are the top hotels in Oyster Pond?
Get your escape off to a great start by booking a stay at Literally Oceanfront Villa Alabaster. It's one of most popular properties in Oyster Pond. Another comfortable option is Les Balcons d'Oyster Pond.
How far in advance should I book my Oyster Pond vacation?
While not all air carriers advertise ticket prices early, you can usually look up international flights on Expedia up to a year in advance. This is the time you can nab some fantastic deals. If you're booking late, there's a chance you could get lucky. Low prices occasionally become available only weeks before departure.
What does an Expedia Oyster Pond travel package include?
It comes down to what sort of trip you're planning. Oyster Pond vacation deals can include car rentals, flights and hotels. You can mix and match to create the travel package that suits you. You can also add on experiences and activities after you've booked to pick up even bigger discounts.
What should I know before booking an Oyster Pond travel package?
A travel package can be easier on the hip pocket than individually booking all you need for your escape. For example, combine your flights, hotels and rental cars and save a packet. No matter your vacation goals, there's bound to be a package that best suits your budget.
Can I choose my airline with an Oyster Pond Expedia vacation package?
With a vacation package, the choice is in your hands. Whether you're looking to fly to Oyster Pond in economy or business class, simply choose from the available airline options. Expedia has access to more than 550 airline partners worldwide.
If I'm not able to travel, can I cancel my Oyster Pond vacation package?
It's impossible to predict what the future holds, so it's comforting to know that you can change or cancel your Oyster Pond vacation package. If you booked in the last 24 hours, you may be eligible for a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal for further details.

Stay near popular Oyster Pond attractions

A coastal landscape with clear turquoise waters, a sandy beach, and a cluster of houses on a hillside.

Dawn Beach

8.4/10 (222 reviews)
Why not spend a carefree afternoon at Dawn Beach during your travels in Oyster Pond? Stroll along the seaside in this relaxing area, or check out its top-notch restaurants.
See properties

Things to do

Sand Dollar Snorkeling Adventure

Half Day Snorkeling Adventure

CA $92
per adult
100% of travellers recommend
Half Day Snorkeling Adventure
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

CA $226
per adult
90% of travellers recommend
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
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
See all activities in Oyster Pond
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.