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
Price was $785, price is now $538 per person
$538
per person
Sep 6 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
This hotel features an outdoor pool and a 24-hour gym. Families will appreciate the waterslide, onsite laundry facilities, and in-room childcare. Guests will appreciate free perks like free self parking and WiFi in public areas.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Save 100% on your flight
Price was $1,508, price is now $728 per person
$728
per person
Sep 5 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
A marina, 3 restaurants, and 6 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. There's fun for all ages with a children's pool and a waterslide, and barbecue grills are available on site.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Save 100% on your flight
Price was $1,256, price is now $649 per person
$649
per person
Sep 5 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
This smoke-free resort features a private beach, a full-service spa, and a marina. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site.
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Save 100% on your flight
Price was $1,296, price is now $863 per person
$863
per person
Sep 17 - Sep 22
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
A restaurant and a bar/lounge are featured at this hotel. Dine at the beachfront restaurant and relax with beach umbrellas. WiFi in public areas is free.
Hotel La Plantation

Hotel La Plantation

4 out of 5
Price was $960, price is now $664 per person
$664
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
This hotel's 3 restaurants, 3 bars/lounges, and outdoor pool are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and airport pick-up service. Relax with a drink at the poolside bar and enjoy free perks like self-serve breakfast and free self parking.
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,006, price is now $735 per person
$735
per person
Sep 6 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
This hotel's 4 restaurants and 3 outdoor pools are some of the featured amenities. Guests will appreciate free perks like free self parking and WiFi in public areas. Dry cleaning, luggage storage, and concierge services are also on offer.

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 $538 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 1,000,000 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!

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
$272 nightly
The price is $285 total per night
$285 total
Jul 1 - Jul 2
Total with taxes and fees
This smoke-free resort features a private beach, a full-service spa, and a marina. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site.
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
$135 nightly
The price is $142 total per night
$142 total
Jul 19 - Jul 20
Total with taxes and fees
This resort features a bar/lounge, a poolside bar, and an outdoor pool. Enjoy the gym and perks like free self parking and free WiFi. A 24-hour business center, a snack bar/deli, and laundry facilities are also on offer.
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
$316 nightly
The price is $331 total per night
$331 total
Jul 23 - Jul 24
Total with taxes and fees
A marina, 3 restaurants, and 6 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. There's fun for all ages with a children's pool and a waterslide, and barbecue grills are available on site.
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.