Cay Bay Hill Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Cay Bay Hill Vacation

When a fun city break is calling, answer it with a Cay Bay Hill vacation package. The neighborhood of Upper Princes Quarter, which is great for shopping, coastal beaches and nature, makes an awesome base for your adventures. Fill your spare time with visits to Little Bay Beach, Sint Maarten Park and Guana Bay Beach, some of the attractions you shouldn't miss during your trip to Cay Bay Hill. A couple of quick clicks is all it takes to create your perfect Cay Bay Hill vacation on Expedia.

Top Cay Bay Hill Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
per person
Sep. 3 - Sep. 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Philipsburg (SXM)
8.8/10 Excellent! (1,000 reviews)
Love it, will definitely come back before the year out!

Reviewed on Jun. 17, 2024

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
per person
Jul. 17 - Jul. 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
9.2/10 Wonderful! (1,000 reviews)
Great hotel, located in a great area. The pool area and bar were nice, however, the pool does not have a shallow area to hangout. The rooms were updated and clean, only thing that was missing was a long mirror but otherwise it’s a great hotel for a great price !

Reviewed on Jun. 16, 2024

La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
per person
Jul. 17 - Jul. 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
9.4/10 Exceptional! (408 reviews)
Close proximity to restaurants, shops and beach were great!

Reviewed on Jun. 8, 2024

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
per person
Jul. 17 - Jul. 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
9.2/10 Wonderful! (784 reviews)
Just wish the hotel had a restaurant on the property.

Reviewed on Jun. 8, 2024

Coral Beach Club Villas & Marina

Coral Beach Club Villas & Marina

4 out of 5
Oyster Pond
Save 100% on your flight
per person
Jul. 17 - Jul. 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
9.2/10 Wonderful! (104 reviews)
We stayed in the "penthouse" villa, which was fantastic. Clean, modern, well-appointed, large. Great housekeeping, friendly staff, convenient amenities. The area itself is a bit away from things so you have to want that, which we did.

Reviewed on Apr. 1, 2024

Cay Bay Hill Hotel Deals

Sonesta Maho Beach All Inclusive Resort Casino & Spa
Sonesta Maho Beach All Inclusive Resort Casino & Spa
4 out of 5
1 Rhine Road, Maho Bay, Lowlands
The price is CA $309 per night from Jun. 18 to Jun. 19
CA $309
CA $374 total
includes taxes & fees
Jun 18 - Jun 19
7.8/10 Good! (1,729 reviews)
"Had a problem with construction noise on the sixth floor but “Oneca” fixed the problem by moving us to the other side of the floor. Dining options for the wife was great. She doesn’t eat seafood and a lot of the resorts food in our travels she has a dislike for. Yet here she found that the food was ..."

Reviewed on Jun. 15, 2024

Sonesta Maho Beach All Inclusive Resort Casino & Spa
The Morgan Resort Spa Village
The Morgan Resort Spa Village
4 out of 5
2 Beacon Hill Road, Simpson Bay
Fully refundableReserve now, pay when you stay
The price is CA $387 per night from Jun. 30 to Jul. 1
CA $387
CA $492 total
includes taxes & fees
Jun 30 - Jul 1
9/10 Wonderful! (1,274 reviews)
"The property was beautiful. Looks like just the pictures on their website. The location is perfect. Bars, restaurants, casino and beach within walking distance."

Reviewed on Jun. 13, 2024

The Morgan Resort Spa Village
Simpson Bay Resort, Marina & Spa
Simpson Bay Resort, Marina & Spa
4 out of 5
Billy Folly Road 37, Simpson Bay
Fully refundableReserve now, pay when you stay
The price is CA $160 per night from Jun. 24 to Jun. 25
CA $160
CA $193 total
includes taxes & fees
Jun 24 - Jun 25
8.6/10 Excellent! (1,005 reviews)
"Privacy Friendly front desk staff"

Reviewed on Jun. 16, 2024

Simpson Bay Resort, Marina & Spa
See all 3,565 properties in Cay Bay Hill
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Cay Bay Hill vacation package cost?
Create unforgettable memories with our Cay Bay Hill vacation packages, which start from only CA $1,208. Choose the hotels and flights that fit your travel plans. Then, add on some sightseeing tours to cap off your unique adventure.
How do I get a cheap travel package to Cay Bay Hill?
Combine your hotels and flights, add on extras such as activities, and save with a Cay Bay Hill vacation package. You won’t just enjoy awesome discounts on your escape — you’ll have loads of choice at your fingertips too. When you book through Expedia, you can choose from more than 550 airlines and 1,000,000 properties across the globe. Your affordable vacation begins right here, right now!
Where should I stay in Cay Bay Hill?
We recommend staying near the action. Many people favor hotels in the vicinity of top attractions, such as Sint Maarten Park, Little Bay Beach and Fort Amsterdam.
What are the top hotels in Cay Bay Hill?
Lock in a room at Modern Tropical Villa. It’s one of the neighborhood’s most sought-after hotels. Another top-rated option in Cay Bay Hill is Villa Ocean - Indulge Yourself In Paradise.
How far in advance should I book my Cay Bay Hill vacation?
It can be hard to know when is the ideal time to book your Cay Bay Hill vacation. But usually the earlier you book, the cheaper the prices. In some cases, you can book your flights and hotels nearly a year before departure. If you’re hoping for a last-minute getaway, no need to stress! There are plenty of fantastic bargains announced on Expedia every day.
What does an Expedia Cay Bay Hill travel package include?
That depends on you. You can select from a range of Cay Bay Hill packages, such as a flight, hotel and rental car. You can also book a flight with a hotel, or a flight and a rental car. Once you’ve made your booking, you can add the fun stuff like experiences and tours. Whatever your ideal Cay Bay Hill vacation looks like, get ready to save!
Can I choose my airline with a Cay Bay Hill Expedia vacation package?
Expedia has access to more than 550 partner airlines globally, so you certainly can. Simply choose the airline you want and create the perfect Cay Bay Hill escape.
If I'm not able to travel, can I cancel my Cay Bay Hill vacation package?
Yes, you can. We realize life happens, so we’re happy to help if you have to make changes to your Cay Bay Hill vacation package. You may be able to amend or cancel your itinerary for free if you’ve booked within 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Take a look at our Customer Service Portal for further information. Also, check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Cay Bay Hill

Image for Great Bay Beach

Great Bay Beach

4/5(20 reviews)

If a restful vacation is part of your travel plans, Great Bay Beach might be the perfect place to seek out during your trip to Philipsburg. Check out the shops and top-notch restaurants in this romantic area.

Great Bay Beach
Image for Philipsburg Boardwalk

Philipsburg Boardwalk

Philipsburg Boardwalk is just one of the places to see in Philipsburg, so why not enjoy the other things to explore during your travels? Stroll along the area's beaches or simply enjoy its restaurants.

Philipsburg Boardwalk
Image for Guana Bay Beach

Guana Bay Beach

5/5(2 reviews)

The picturesque shores of this tranquil bay provide a great opportunity to escape the crowds and jump in the crystal clear water for surfing or swimming.

Guana Bay Beach

What to do in Cay Bay Hill

Image for Sunset Champagne Cruise in St. Maarten

Sunset Champagne Cruise in St. Maarten

CA $68
Per adult
100% of travellers recommend
Sunset Champagne Cruise in St. Maarten
Image for Catamaran Day Sail / Snorkel / Cruise in St Maarten / St Martin

Catamaran Day Sail / Snorkel / Cruise in St Maarten / St Martin

CA $172
Per adult
Catamaran Day Sail / Snorkel / Cruise in St Maarten / St Martin
See all activities in Cay Bay Hill
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.