Exclusive Hollywood Casino Vacation Deals

Hollywood Casino vacation package deals

Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Save 100% on your flight
per person
Jul. 19 - Jul. 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Philipsburg (SXM)
Stay at this 3.5-star 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 Orient Bay Beach and Grand Case Beach are located nearby.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
per person
Jul. 19 - Jul. 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Philipsburg (SXM)
Stay at this 4-star 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 Orient Bay Beach are located nearby.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
per person
Jul. 21 - Jul. 25
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Philipsburg (SXM)
Stay at this 4-star 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.
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
per person
Jul. 19 - Jul. 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Philipsburg (SXM)
Stay at this 4-star 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.
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Save 100% on your flight
per person
Jul. 19 - Jul. 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Philipsburg (SXM)
Stay at this 4-star beach hotel in Philipsburg. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Orient Bay Beach and Maho Beach are located nearby.
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Save 100% on your flight
per person
Jul. 6 - Jul. 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Philipsburg (SXM)
Stay at this 4-star hotel in Philipsburg. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Maho Beach and Orient 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 $1,055 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 $158 per night
CA $158
CA $190 total
Jun 9 - Jun 10
includes taxes & fees
Stay at this 4-star 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

3.5 out of 5
Pelican Key, Simpson Bay, 6 Billy Folly, Simpson Bay
Free cancellation
Reserve now, pay when you stay
The price is CA $143 per night
CA $143
CA $186 total
May 29 - May 30
includes taxes & fees
Stay at this 3.5-star 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 $186 per night
CA $186
CA $224 total
May 18 - May 19
includes taxes & fees
Stay at this 4-star 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 Orient 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.

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