Exclusive Hollywood Casino Vacation Deals

Hollywood Casino vacation package deals

Price found within the past 48 hours. Click for updated prices.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was CA $3,008, price is now CA $1,331 per person
CA $1,331
per person
Jul 23 - Jul 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was CA $3,128, price is now CA $1,364 per person
CA $1,364
per person
Aug 3 - Aug 10
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was CA $2,306, price is now CA $1,483 per person
CA $1,483
per person
Jun 30 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Philipsburg (SXM)
Book a stay at this family-friendly hotel in Oyster Pond. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grand Case Beach and Dawn Beach are located nearby.
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was CA $2,300, price is now CA $1,484 per person
CA $1,484
per person
Jul 23 - Jul 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
Book a stay at this beach hotel in Orient Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Grand Case Beach and Green Cay are located nearby.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Price was CA $2,108, price is now CA $1,461 per person
CA $1,461
per person
Jun 30 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Philipsburg (SXM)
Book a stay at this beach resort in Oyster Pond. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Grand Case Beach and Oyster Bay Marina are located nearby.
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was CA $2,418, price is now CA $1,678 per person
CA $1,678
per person
Jul 23 - Jul 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
Book a stay at this spa resort in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.

Frequently asked questions

How much are vacation packages to Hollywood Casino?
Let Travelocity take all the stress out of organizing your next big trip to Hollywood Casino. Book our awesome CA $1,331 package deal and save both money and time. With your hotel and flights sorted, you can concentrate on the fun parts of your adventure — like visiting those must-do attractions!
Where can I get the best vacation package deals for Hollywood Casino?
Travelocity has endless ways to score an awesome Hollywood Casino package deal. Select from as many as 400 partner airlines and 665,000 properties around the globe and craft a vacation package that's suited to you. With almost endless choice, it's time to start planning your next big adventure.
Why should I purchase my Hollywood Casino vacation package with Travelocity?
By booking your flights, hotel, activities and car rental altogether, you'll save time and money. We have a dedicated team of experts available 24/7, and you'll know that you're always getting the lowest price possible with our Price Match Guarantee. So, what's stopping you? Book the vacation of your dreams today and get packing!
Can I go on vacation to Hollywood Casino at this time?
We have the local knowledge to help make your vacation dreams come true, so before arranging your trip to Hollywood Casino, take a look at our Covid-19 Travel Advisor. Here you'll discover up-to-date info on quarantine policies, travel restrictions and much more.

Top Hollywood Casino hotel deals

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Billy Folly Road 37 Simpson Bay
Free cancellation
Reserve now, pay when you stay
The price is CA $300 per night
CA $300
CA $367 total
Jun 15 - Jun 16
includes taxes & fees
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
On private beach
Pool
Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

4 out of 5
Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay
The price is CA $174 per night
CA $174
CA $219 total
Jun 14 - Jun 15
includes taxes & fees
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
Pool
Parking included
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Billy Folly Road No. 37A Simpson Bay
Free cancellation
Reserve now, pay when you stay
The price is CA $357 per night
CA $357
CA $438 total
Jun 15 - Jun 16
includes taxes & fees
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
Pool
Parking included
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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.