Happy Bay Flight + Hotel Packages

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

Hilton Vacation Club Flamingo Beach St. Maarten

per person

Sep 29 - Oct 6

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 a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.

Simpson Bay Resort, Marina & Spa

Save 100% on your flight

per person

Sep 29 - Oct 6

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 Mullet Bay Beach are located nearby.

The Villas at Simpson Bay Resort

Save 100% on your flight

per person

Sep 29 - Oct 6

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 Orient Bay Beach and Maho Beach are located nearby.

Sapphire Beach Club Resort

per person

Sep 29 - Oct 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

Stay at this 3-star beach resort in Lowlands. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Mullet Bay Beach and Maho Beach are located nearby.

Princess Heights Luxury Boutique Condo Hotel

Save 100% on your flight

per person

Sep 29 - Oct 6

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.

Oyster Bay Beach Resort

Save 100% on your flight

per person

Sep 29 - Oct 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

Stay at this 4-star beach resort in Oyster Pond. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Orient Bay Beach and Grand Case Beach are located nearby.

Holland House Beach Hotel

Save 100% on your flight

per person

Sep 29 - Oct 6

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.

Divi Little Bay Beach Resort

Save 100% on your flight

per person

Sep 29 - Oct 6

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 Orient Bay Beach and Maho Beach are located nearby.

Esmeralda Resort

per person

Oct 8 - Oct 15

found 19 hours 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 helpful staff in our reviews. Popular attractions Orient Bay Beach and Grand Case Beach are located nearby.

The Atrium Beach Resort and Spa, Ascend Hotel Collection

per person

Sep 29 - Oct 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

Stay at this 3-star 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 attractions Orient Bay Beach and Maho Beach are located nearby.

Oceans at Divi Little Bay

Save 100% on your flight

per person

Sep 29 - Oct 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

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

Horizon View Beach Hotel

per person

Sep 29 - Oct 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

Stay at this 3-star beach hotel in Philipsburg. Enjoy free WiFi, a beach locale, and 5 beach bars. Our guests praise the helpful staff in our reviews. Popular attractions Orient Bay Beach and Maho Beach are located nearby.