Orient Bay Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

Princess Heights Luxury Boutique Condo Hotel

Save 100% on your flight

per person

Jun 21 - Jun 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Simpson Bay Resort, Marina & Spa

Save 100% on your flight

per person

Jun 25 - Jun 30

found 14 hours ago

Roundtrip non-stop flight included

Boston (BOS) 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 Villas at Simpson Bay Resort

Save 100% on your flight

per person

Jun 11 - Jun 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

La Playa Orient Bay

Save 100% on your flight

per person

Jun 21 - Jun 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

Stay at this 4-star beach hotel in Orient Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Orient Bay Beach and Grand Case Beach are located nearby.

Divi Little Bay Beach Resort

Save 100% on your flight

per person

Jun 15 - Jun 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

Stay at this 4-star beach resort in Philipsburg. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maho Beach and Orient Bay Beach are located nearby.

Holland House Beach Hotel

per person

Jun 21 - Jun 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Hilton Vacation Club Royal Palm St. Maarten

per person

Jun 21 - Jun 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

Stay at this 3.5-star beach resort in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Maho Beach and Orient Bay Beach are located nearby.

The Morgan Resort Spa Village

per person

Jun 21 - Jun 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Orient Bay Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

Save 100% on your flight

per person

Jun 21 - Jun 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)