Title: Cay Bay Hill Vacation Packages & Trips 2025/2026 from CA $1,329 | Expedia.ca [Hotels in Cay Bay Hill](https://expedia.ca/Cay-Bay-Hill-Hotels.d553248635976196227.Travel-Guide-Hotels)[Vacation Rentals in Cay Bay Hill](https://expedia.ca/Cay-Bay-Hill-Vacation-Rentals.d553248635976196227.Travel-Guide-VacationRentals)[Cay Bay Hill Car Rentals](https://expedia.ca/Car-Rentals-In-Cay-Bay-Hill.d553248635976196227.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Cay Bay Hill Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### 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](https://www.expedia.ca/Little-Bay-Beach-Philipsburg.d553248621532873750.Vacation-Attraction), [Sint Maarten Park](https://www.expedia.ca/Sint-Maarten-Park-Philipsburg.d553248621533158276.Vacation-Attraction) and [Guana Bay Beach](https://www.expedia.ca/Guana-Bay-Beach-Philipsburg.d506436.Vacation-Attraction), 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. ![Princess Heights Luxury Boutique Condo Hotel](https://images.trvl-media.com/lodging/1000000/570000/561400/561365/3eb207bd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Princess Heights Luxury Boutique Condo Hotel Oyster Pond CA $1,329 per person Jan 17 - Jan 22 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Philipsburg (SXM) 9.2/10 Wonderful! (966 reviews) Keep up your awesome work Team Princess Heghts! Your friends Anvar & Svetlana Reviewed on Sep 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-22/?FromAirport=YHM&Destination=SXM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=561365&paandie=true&dealMarker=Gs0ymm4P66-PQ86px8eTF8qNEPMvDw59yPZWzDOBQdMtNc0C90WE7kT-8KOoyCN6) ![The Villas at Simpson Bay Resort](https://images.trvl-media.com/lodging/5000000/4560000/4553800/4553784/7e74429d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Villas at Simpson Bay Resort CA $1,884 per person Jan 17 - Jan 22 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Philipsburg (SXM) 9.2/10 Wonderful! (1,268 reviews) Clean , quiet pool area as compared to all inclusive . Extremely well maintained , manicured . Clean rooms . First floor view was great and conveniently close to pool . Reviewed on Oct 27, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-22/?FromAirport=YHM&Destination=SXM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=4553784&paandie=true&dealMarker=QT9_blIa0KDT9DydLWSQxjwClbIpixZCdgtyoURv8EKThIKrN58YvyeHXhuslS4d) ![Simpson Bay Resort, Marina & Spa](https://images.trvl-media.com/lodging/2000000/1260000/1256900/1256868/30f27be9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Simpson Bay Resort, Marina & Spa Pelican Key CA $1,460 per person Jan 11 - Jan 16 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Philipsburg (SXM) 9/10 Wonderful! (1,398 reviews) Nice, clean, air conditioned rooms with working windows and sliders. Bathroom and kitchen well stocked. House keeping service was excellent. Pools and landscaping beautiful. Towel service. Lots of food choices. I enjoyed the resort very much. Reviewed on Oct 31, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-11/2026-01-16/?FromAirport=YTO&Destination=SXM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1256868&paandie=true&dealMarker=Gs0ymm4P66-PQ86px8eTF9PJt1n-MPCJHvNYVRjQ8ml8G4Rx8910dWb7QA1xKSvl) ![Oceans at Divi Little Bay](https://images.trvl-media.com/lodging/75000000/74270000/74267800/74267774/fee04e6c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Oceans at Divi Little Bay CA $2,128 per person Jan 17 - Jan 22 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Philipsburg (SXM) 8.4/10 Very Good! (262 reviews) The balcony had a ocean view that was very relaxing. The room was clean and the staff was professional and accommodating. Reviewed on Oct 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-22/?FromAirport=YHM&Destination=SXM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=74267774&paandie=true&dealMarker=Gs0ymm4P66-PQ86px8eTFyXbt6HP1y1E0mDx4TI_OAqjahz6xDl4YRLUvK2zMeNb) ![Holland House Beach Hotel](https://images.trvl-media.com/lodging/2000000/1170000/1160500/1160500/ef6e99b8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holland House Beach Hotel Downtown Philipsburg CA $1,656 per person Jan 17 - Jan 22 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Philipsburg (SXM) 9.2/10 Wonderful! (1,000 reviews) The room was spacious very well cleaned and the food was excellent Reviewed on Oct 29, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-22/?FromAirport=YHM&Destination=SXM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1160500&paandie=true&dealMarker=Gs0ymm4P66-PQ86px8eTF_Tl2cff76rEclQc4Isqh8V49XcogtEjEoAKW4x7-hP1) ## Ready to book your vacation to Cay Bay Hill? Choose your dates ## Cay Bay Hill Hotel Deals ![Sonesta Maho Beach All Inclusive Resort Casino & Spa](https://images.trvl-media.com/lodging/1000000/570000/565700/565666/45414036_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sonesta Maho Beach All Inclusive Resort Casino & Spa 1 Rhine Road, Maho Bay, Lowlands CA $437 CA $528 total Nov 17 - Nov 18 includes taxes & fees 7.8/10 Good! (2,692 reviews) Awesome staff. Reviewed on Oct 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=17%2F11%2F2025&endDate=18%2F11%2F2025&selected=565666&PinnedHotelID=565666&HadPinnedHotel=true®ionId=553248635976196227) ![Simpson Bay Resort, Marina & Spa](https://images.trvl-media.com/lodging/2000000/1260000/1256900/1256868/30f27be9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Simpson Bay Resort, Marina & Spa Billy Folly Road 37, Simpson Bay Fully refundableReserve now, pay when you stay CA $165 CA $199 total Nov 23 - Nov 24 includes taxes & fees 8.8/10 Excellent! (1,425 reviews) Yesb Reviewed on Oct 25, 2025 [](https://expedia.ca/Hotel-Search?startDate=23%2F11%2F2025&endDate=24%2F11%2F2025&selected=1256868&PinnedHotelID=1256868&HadPinnedHotel=true®ionId=553248635976196227) ![The Morgan Resort Spa Village](https://images.trvl-media.com/lodging/18000000/17530000/17525000/17524915/bf19cc27_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Morgan Resort Spa Village 2 Beacon Hill Road, Simpson Bay Fully refundable CA $410 CA $522 total Nov 10 - Nov 11 includes taxes & fees 8.8/10 Excellent! (1,855 reviews) Our stay was very nice! The staff were super nice and friendly. I have only one issue and thats with the shower, the bathroom can use an upgrade. Other than that everything else was Amazing. Reviewed on Oct 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=10%2F11%2F2025&endDate=11%2F11%2F2025&selected=17524915&PinnedHotelID=17524915&HadPinnedHotel=true®ionId=553248635976196227) [See all 3,595 properties in Cay Bay Hill](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=02%2F11%2F2025&endDate=03%2F11%2F2025®ionId=553248635976196227) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Discover the most popular places to visit in Cay Bay Hill ![Great Bay Beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/523000/523223-great-bay-beach.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.ca/Great-Bay-Beach-Philipsburg.d6338950.Vacation-Attraction) ![Fort Amsterdam which includes château or palace, a ruin and military items](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/48000/48448-Fort-Amsterdam.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Fort Amsterdam 5/5(2 reviews) The remains of the first Dutch military base in the Caribbean offer stunning views across the ocean and over the town of Philipsburg behind it. [](https://expedia.ca/Fort-Amsterdam-Philipsburg.d502879.Vacation-Attraction) ![Guana Bay Beach featuring cuddly or friendly animals, landscape views and a sandy beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/48000/48411-Guana-Bay-Beach.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.ca/Guana-Bay-Beach-Philipsburg.d506436.Vacation-Attraction) ### What to do in Cay Bay Hill ![Sand Dollar Snorkeling Adventure](https://mediaim.expedia.com/localexpert/253868/cee07738-52cd-498c-b693-2512d348c7bb.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Half Day Snorkeling Adventure CA $91 per adult **100%** of travellers recommend [](https://expedia.ca/things-to-do/half-day-snorkeling-adventure.a253868.activity-details) ![Panoramic view of vibrant St. Martin ](https://mediaim.expedia.com/localexpert/413439/1889a377-cdfa-4a6e-bdf7-cb7a36cef979.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Edge Ferry Tickets to St. Barts CA $140 per adult **84%** of travellers recommend [](https://expedia.ca/things-to-do/edge-ferry-tickets-to-st-barts.a413439.activity-details) ![Tango Sunset Dinner Cruise](https://mediaim.expedia.com/localexpert/253878/9105e861-0cf5-4207-8f5b-f751a25f46b2.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Tango Sunset Cruise with Caribbean Dinner & Open Bar CA $118 per adult **94%** of travellers recommend [](https://expedia.ca/things-to-do/tango-sunset-cruise-with-caribbean-dinner-open-bar.a253878.activity-details) [See all activities in Cay Bay Hill](https://expedia.ca/things-to-do/search?rid=553248635976196227) ## 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. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)