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
Price was $1,047, price is now $605 per person
$605
per person
Jul 8 - Jul 13
found 1 day 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.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was $1,543, price is now $682 per person
$682
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip non-stop 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
Pelican Key
Save 100% on your flight
Price was $2,160, price is now $1,070 per person
$1,070
per person
Jul 19 - Jul 24
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.
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Point Blanche
Save 100% on your flight
Price was $1,361, price is now $861 per person
$861
per person
Jul 8 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
An outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A terrace, a garden, and a virtual front desk are also on offer.
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,460, price is now $963 per person
$963
per person
Jul 19 - Jul 24
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. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Families will appreciate the onsite laundry facilities and in-room childcare.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Save 100% on your flight
Price was $950, price is now $638 per person
$638
per person
Jul 8 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
This resort features a full-service spa, a marina, and 2 restaurants. Families will appreciate the children's pool, onsite laundry facilities, and in-room childcare. Enjoy the outdoor pool and perks like free WiFi.

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 $605 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
$239 nightly
The price is $250 total per night
$250 total
May 14 - May 15
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
$144 nightly
The price is $151 total per night
$151 total
May 18 - May 19
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
$283 nightly
The price is $297 total per night
$297 total
May 17 - May 18
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.