$171 Cheap flight deals from Portland (PDX) to Kennebunkport (PWM)

This Weekend's Flight Deals from Portland to Kennebunkport

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Jul 27 - Wed, Aug 13
PDX
Portland Intl.
PWM
Portland Intl. Jetport
$417 Roundtrip, found 1 day ago
$417
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Jul 27 from Portland Intl. to Portland Intl. Jetport, returning Wed, Aug 13, priced at $417 found 1 day ago

Airfares from $171 One Way, $333 Round Trip from Portland to Kennebunkport

Prices starting at $333 for return flights and $171 for one-way flights to Kennebunkport were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Sep 29 - Thu, Oct 2
PDX
Portland
PWM
Portland
$333 Roundtrip, found 10 hours ago
$333
Roundtrip
found 10 hours ago
Select Delta flight, departing Mon, Sep 29 from Portland to Portland, returning Thu, Oct 2, priced at $333 found 10 hours ago
Tue, Sep 30 - Thu, Oct 2
PDX
Portland
PWM
Portland
$338 Roundtrip, found 10 hours ago
$338
Roundtrip
found 10 hours ago
Select Delta flight, departing Tue, Sep 30 from Portland to Portland, returning Thu, Oct 2, priced at $338 found 10 hours ago
Sun, Aug 31 - Sat, Sep 6
PDX
Portland
PWM
Portland
$340 Roundtrip, found 1 day ago
$340
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Sun, Aug 31 from Portland to Portland, returning Sat, Sep 6, priced at $340 found 1 day ago
Sat, Aug 23 - Sat, Aug 30
PDX
Portland
PWM
Portland
$343 Roundtrip, found 2 days ago
$343
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Aug 23 from Portland to Portland, returning Sat, Aug 30, priced at $343 found 2 days ago
Sun, Aug 31 - Sat, Sep 6
PDX
Portland
PWM
Portland
$347 Roundtrip, found 1 day ago
$347
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Aug 31 from Portland to Portland, returning Sat, Sep 6, priced at $347 found 1 day ago

Kennebunkport economy flight packages

Price found within the past 48 hours. Click for updated prices.
Chebeague Island Inn
4.0-star property

Chebeague Island Inn

8.8/10 Excellent! (72 reviews)

Aug 31 - Sep 5

5 night stay

Portland (PDX) to Portland (PWM)

United • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Such a beautiful place! We had a great time riding bikes around the island.

Reviewed on Jun 18, 2019

Portland Harbor Hotel
4.0-star property

Portland Harbor Hotel

9.2/10 Wonderful! (1,523 reviews)

Aug 31 - Sep 5

5 night stay

Portland (PDX) to Portland (PWM)

United • Non-stop roundtrip • Coach
per person
found 1 day ago
Friendly staff and nice facilities

Reviewed on Jul 17, 2025

The Docent's Collection
3.5-star property

The Docent's Collection

9.6/10 Exceptional! (211 reviews)

Aug 31 - Sep 5

5 night stay

Portland (PDX) to Portland (PWM)

United • Non-stop roundtrip • Coach
per person
found 1 day ago
This is a beautiful property with amazing, helpful staff at a prime location. Close to lots of dining and activities, a perfect winter wonderland retreat. It is a very relaxing place to stay.

Reviewed on Mar 10, 2023

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