Exclusive Hollywood Casino Vacation Deals

Hollywood Casino vacation package deals

Price found within the past 48 hours. Click for updated prices.
Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

4 out of 5
Save 100% on your flight
Price was $1,083, price is now $650 per person
$650
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free aparthotel. Enjoy the gym and perks like free self parking and free WiFi. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was $2,561, price is now $1,206 per person
$1,206
per person
Dec 18 - Dec 24
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
Price was $1,800, price is now $894 per person
$894
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,243, price is now $783 per person
$783
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Families will appreciate the onsite laundry facilities and babysitting. Relax with a drink at the beach bar and enjoy free perks like English breakfast and free self parking.
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Save 100% on your flight
Price was $5,862, price is now $3,693 per person
$3,693
per person
Dec 26 - Jan 2
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was $3,214, price is now $2,072 per person
$2,072
per person
Dec 26 - Jan 2
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) 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.

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 $650 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
$121 nightly
The price is $126 total per night
$126 total
Oct 19 - Oct 20
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
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $119 total per night
$119 total
Oct 13 - Oct 14
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
$148 nightly
The price is $155 total per night
$155 total
Oct 8 - Oct 9
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.