Flights from Middletown to Simpson Bay

Cheapest flights from Middletown

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Jun 8 - Sat, Jun 14

MDT

Harrisburg Intl.

SXM

Princess Juliana Intl.

$521 Roundtrip, found 21 hours ago

$521

Roundtrip

found 21 hours ago

Select Frontier Airlines flight, departing Sun, Jun 8 from Harrisburg Intl. to Princess Juliana Intl., returning Sat, Jun 14, priced at $521 found 21 hours ago

Thu, Jun 5 - Sat, Jun 14

MDT

Harrisburg Intl.

SXM

Princess Juliana Intl.

$547 Roundtrip, found 21 hours ago

$547

Roundtrip

found 21 hours ago

Select Frontier Airlines flight, departing Thu, Jun 5 from Harrisburg Intl. to Princess Juliana Intl., returning Sat, Jun 14, priced at $547 found 21 hours ago

Wed, Jun 4 - Wed, Jun 11

MDT

Harrisburg Intl.

SXM

Princess Juliana Intl.

$627 Roundtrip, found 21 hours ago

$627

Roundtrip

found 21 hours ago

Select American Airlines flight, departing Wed, Jun 4 from Harrisburg Intl. to Princess Juliana Intl., returning Wed, Jun 11, priced at $627 found 21 hours ago

Wed, Jun 4 - Tue, Jun 17

MDT

Harrisburg Intl.

SXM

Princess Juliana Intl.

$632 Roundtrip, found 21 hours ago

$632

Roundtrip

found 21 hours ago

Select American Airlines flight, departing Wed, Jun 4 from Harrisburg Intl. to Princess Juliana Intl., returning Tue, Jun 17, priced at $632 found 21 hours ago

Thu, Jun 5 - Wed, Jun 11

MDT

Harrisburg Intl.

SXM

Princess Juliana Intl.

$645 Roundtrip, found 21 hours ago

$645

Roundtrip

found 21 hours ago

Select United flight, departing Thu, Jun 5 from Harrisburg Intl. to Princess Juliana Intl., returning Wed, Jun 11, priced at $645 found 21 hours ago

Fri, Jun 6 - Wed, Jun 11

MDT

Harrisburg Intl.

SXM

Princess Juliana Intl.

$652 Roundtrip, found 21 hours ago

$652

Roundtrip

found 21 hours ago

Select United flight, departing Fri, Jun 6 from Harrisburg Intl. to Princess Juliana Intl., returning Wed, Jun 11, priced at $652 found 21 hours ago

Thu, Jun 5 - Fri, Jun 13

MDT

Harrisburg Intl.

SXM

Princess Juliana Intl.

$663 Roundtrip, found 21 hours ago

$663

Roundtrip

found 21 hours ago

Select United flight, departing Thu, Jun 5 from Harrisburg Intl. to Princess Juliana Intl., returning Fri, Jun 13, priced at $663 found 21 hours ago

Tue, Jun 10 - Wed, Jun 11

MDT

Harrisburg Intl.

SXM

Princess Juliana Intl.

$691 Roundtrip, found 21 hours ago

$691

Roundtrip

found 21 hours ago

Select Delta flight, departing Tue, Jun 10 from Harrisburg Intl. to Princess Juliana Intl., returning Wed, Jun 11, priced at $691 found 21 hours ago

Sun, Jun 8 - Wed, Jun 11

MDT

Harrisburg Intl.

SXM

Princess Juliana Intl.

$701 Roundtrip, found 21 hours ago

$701

Roundtrip

found 21 hours ago

Select United flight, departing Sun, Jun 8 from Harrisburg Intl. to Princess Juliana Intl., returning Wed, Jun 11, priced at $701 found 21 hours ago

Sun, Jun 8 - Thu, Jun 12

MDT

Harrisburg Intl.

SXM

Princess Juliana Intl.

$710 Roundtrip, found 21 hours ago

$710

Roundtrip

found 21 hours ago

Select American Airlines flight, departing Sun, Jun 8 from Harrisburg Intl. to Princess Juliana Intl., returning Thu, Jun 12, priced at $710 found 21 hours ago

Wed, Jun 4 - Sun, Jun 15

MDT

Harrisburg Intl.

SXM

Princess Juliana Intl.

$736 Roundtrip, found 21 hours ago

$736

Roundtrip

found 21 hours ago

Select American Airlines flight, departing Wed, Jun 4 from Harrisburg Intl. to Princess Juliana Intl., returning Sun, Jun 15, priced at $736 found 21 hours ago

Fri, Jun 6 - Thu, Jun 12

MDT

Harrisburg Intl.

SXM

Princess Juliana Intl.

$742 Roundtrip, found 21 hours ago

$742

Roundtrip

found 21 hours ago

Select American Airlines flight, departing Fri, Jun 6 from Harrisburg Intl. to Princess Juliana Intl., returning Thu, Jun 12, priced at $742 found 21 hours ago

Sat, Jun 7 - Sun, Jun 15

MDT

Harrisburg Intl.

SXM

Princess Juliana Intl.

$745 Roundtrip, found 21 hours ago

$745

Roundtrip

found 21 hours ago

Select American Airlines flight, departing Sat, Jun 7 from Harrisburg Intl. to Princess Juliana Intl., returning Sun, Jun 15, priced at $745 found 21 hours ago

Tue, Jun 10 - Thu, Jun 12

MDT

Harrisburg Intl.

SXM

Princess Juliana Intl.

$753 Roundtrip, found 21 hours ago

$753

Roundtrip

found 21 hours ago

Select American Airlines flight, departing Tue, Jun 10 from Harrisburg Intl. to Princess Juliana Intl., returning Thu, Jun 12, priced at $753 found 21 hours ago

Wed, Jun 4 - Sat, Jun 14

MDT

Harrisburg Intl.

SXM

Princess Juliana Intl.

$760 Roundtrip, found 21 hours ago

$760

Roundtrip

found 21 hours ago

Select United flight, departing Wed, Jun 4 from Harrisburg Intl. to Princess Juliana Intl., returning Sat, Jun 14, priced at $760 found 21 hours ago

Sun, Jun 8 - Fri, Jun 13

MDT

Harrisburg Intl.

SXM

Princess Juliana Intl.

$762 Roundtrip, found 21 hours ago

$762

Roundtrip

found 21 hours ago

Select American Airlines flight, departing Sun, Jun 8 from Harrisburg Intl. to Princess Juliana Intl., returning Fri, Jun 13, priced at $762 found 21 hours ago

Mon, Jun 9 - Sun, Jun 15

MDT

Harrisburg Intl.

SXM

Princess Juliana Intl.

$773 Roundtrip, found 21 hours ago

$773

Roundtrip

found 21 hours ago

Select American Airlines flight, departing Mon, Jun 9 from Harrisburg Intl. to Princess Juliana Intl., returning Sun, Jun 15, priced at $773 found 21 hours ago

Fri, Jun 6 - Sat, Jun 14

MDT

Harrisburg Intl.

SXM

Princess Juliana Intl.

$785 Roundtrip, found 21 hours ago

$785

Roundtrip

found 21 hours ago

Select United flight, departing Fri, Jun 6 from Harrisburg Intl. to Princess Juliana Intl., returning Sat, Jun 14, priced at $785 found 21 hours ago

Tue, Jun 10 - Sat, Jun 14

MDT

Harrisburg Intl.

SXM

Princess Juliana Intl.

$797 Roundtrip, found 21 hours ago

$797

Roundtrip

found 21 hours ago

Select United flight, departing Tue, Jun 10 from Harrisburg Intl. to Princess Juliana Intl., returning Sat, Jun 14, priced at $797 found 21 hours ago

Tue, Jun 10 - Fri, Jun 13

MDT

Harrisburg Intl.

SXM

Princess Juliana Intl.

$802 Roundtrip, found 21 hours ago

$802

Roundtrip

found 21 hours ago

Select Delta flight, departing Tue, Jun 10 from Harrisburg Intl. to Princess Juliana Intl., returning Fri, Jun 13, priced at $802 found 21 hours ago