Vacations Close To Hollywood Casino

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Hollywood Casino Flight + Hotel packages

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 $1,599, price is now $874 per person
$874
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Philipsburg (SXM)

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $2,464, price is now $1,028 per person
$1,028
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Philipsburg (SXM)
This resort was amazing. Walking distance to many restaurants and club. They call taxis for you 24/7 to where ever and back. Property is also very beautiful. I only tried one restaurant on property, Juliettes Bistro for breakfast, it was really good and the staff were really nice. I will definitely be back.

Reviewed on Sep 12, 2026

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $2,452, price is now $1,411 per person
$1,411
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Philipsburg (SXM)

La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,693, price is now $1,155 per person
$1,155
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Philipsburg (SXM)
Fabulous stay! Beautiful resort right on Orient Bay!

Reviewed on Aug 26, 2026

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Save 100% on your flight
Price was $1,578, price is now $1,125 per person
$1,125
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Philipsburg (SXM)

Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Price was $1,271, price is now $908 per person
$908
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Philipsburg (SXM)

Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was $1,510, price is now $1,101 per person
$1,101
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Philipsburg (SXM)

Hotel La Plantation

Hotel La Plantation

4 out of 5
Price was $1,326, price is now $992 per person
$992
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Philipsburg (SXM)
Best place ever

Reviewed on Sep 8, 2026

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Best Lodging Options Near Hollywood Casino

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Billy Folly Road 37 Simpson Bay
0.13 km from Hollywood Casino
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 ...
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Billy Folly Road No. 37A Simpson Bay
0.21 km from Hollywood Casino
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 ...
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
0.15 km from Hollywood Casino
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. ...
The Atrium Beach Resort and Spa, an Ascend Collection Resort

The Atrium Beach Resort and Spa, an Ascend Collection Resort

3 out of 5
6 Billy Folly Road Simpson Bay
0.37 km from Hollywood Casino
Book a stay at this beach hotel in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

4 out of 5
115 Welfare Road Simpson Bay
0.59 km from Hollywood Casino
Book a stay at this beach aparthotel in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property ...
La Vista Hotel

La Vista Hotel

3 out of 5
Billy Folly Road Simpson Bay Sint Maarten
0.14 km from Hollywood Casino
Book a stay at this beach hotel in Simpson Bay. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Maho Beach and Mullet Bay Beach are located ...
Baker's Suites

Baker's Suites

3.5 out of 5
Spinel Road #2 Simpson Bay
0.33 km from Hollywood Casino
Stay at this hotel in Simpson Bay. Enjoy free WiFi, breakfast (surcharge), and daily housekeeping. Our guests praise the helpful staff and the clean rooms in ...
Commodore Suites, SureStay Collection by Best Western

Commodore Suites, SureStay Collection by Best Western

3.5 out of 5
Welfare Road 109 Simpson Bay
0.45 km from Hollywood Casino
Book a stay at this beach hotel in Simpson Bay. Enjoy free WiFi, free parking, and 2 hot tubs. Our guests praise the helpful staff in our reviews. Popular attractions ...
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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.