Happy 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

Mar 12 - Mar 19

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 Dawn Beach are located nearby.

The Villas at Simpson Bay Resort

Save 100% on your flight

per person

Apr 3 - Apr 7

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.

Oceans at Divi Little Bay

Save 100% on your flight

per person

Mar 12 - Mar 19

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.

Divi Little Bay Beach Resort

Save 100% on your flight

per person

Mar 12 - Mar 19

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

Save 100% on your flight

per person

Mar 16 - Mar 21

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.

Picturesque 4 Bedroom 3 Bath Condo With Pool

per person

Mar 18 - Mar 22

found 16 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

Stay at this 3.5-star apartment in Cul de Sac. Enjoy free WiFi, free parking, and balconies. Popular attractions Maho Beach and Orient Bay Beach are located nearby.

Lovely 3-bed Apartment in Maho

per person

Mar 18 - Mar 22

found 16 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

Stay at this 3.5-star apartment in Lowlands. Enjoy free WiFi, free parking, and balconies. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.

Coral Beach Club Villas & Marina

Save 100% on your flight

per person

Mar 12 - Mar 19

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, free parking, and a full-service spa. Popular attractions Orient Bay Beach and Orient Bay are located nearby.

Horizon View Beach Hotel

Save 100% on your flight

per person

Mar 12 - Mar 19

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.

Esmeralda Resort

Save 100% on your flight

per person

Apr 3 - Apr 10

found 23 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 Mont Vernon are located nearby.

The Morgan Resort Spa Village

per person

Apr 3 - Apr 7

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.

Stunning 2 Bedroom View Condo in Maho

per person

Mar 25 - Apr 1

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

Stay at this 3.5-star apartment in Lower Prince's Quarter. Enjoy free WiFi, free parking, and a garden. Popular attractions Orient Bay Beach and Maho Beach are located nearby.

3-4 Night Vacations in Happy Bay

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