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Freeport Vacation Packages

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Freeport Flight + Hotel Packages

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

The Kennebunk Inn

2.5 out of 5
Price was $949, price is now $750 per person
$750
per person
May 9 - May 16
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Portland (PWM)
Stay at this hotel in Kennebunk. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Dock Square and Kennebunk Free Library are located nearby.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Save 100% on your flight
Price was $2,265, price is now $1,634 per person
$1,634
per person
May 23 - May 30
found 15 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and concierge services. Popular attractions Victoria Mansion and Portland Club are located nearby.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $2,011, price is now $1,484 per person
$1,484
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this luxury resort in Cape Neddick. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Perkins Cove and Marginal Way are located nearby.
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Price was $1,158, price is now $873 per person
$873
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Maine Sports Hall of Fame and Cathedral of the Immaculate Conception are located nearby.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $1,058, price is now $800 per person
$800
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maine Mall and Cross Insurance Arena are located nearby.
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Price was $1,016, price is now $798 per person
$798
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Victoria Mansion and Charles Q. Clapp House are located nearby.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Price was $1,050, price is now $834 per person
$834
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Book a stay at this business-friendly hotel in Ogunquit. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ogunquit Beach and Marginal Way are located nearby.
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,227, price is now $974 per person
$974
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.

Freeport Vacation Packages 3-4 Night Stays

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

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $1,058, price is now $800 per person
$800
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Save 100% on your flight
Price was $2,011, price is now $1,484 per person
$1,484
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $1,411, price is now $1,059 per person
$1,059
per person
May 14 - May 17
found 24 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Portland (PWM)
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Price was $1,050, price is now $834 per person
$834
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)

Freeport Vacation Packages 5-7 Night Stays

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

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,732, price is now $1,175 per person
$1,175
per person
May 23 - May 30
found 15 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $2,265, price is now $1,634 per person
$1,634
per person
May 23 - May 30
found 15 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $2,228, price is now $1,658 per person
$1,658
per person
May 23 - May 30
found 15 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $2,103, price is now $1,576 per person
$1,576
per person
May 23 - May 30
found 15 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

American Airlines
Thu, Apr 9 - Mon, Apr 13
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Apr 9 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Mon, Apr 13, priced at $189 found 1 day ago
Breeze Airways
Sat, Aug 22 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$190 Roundtrip, found 2 hours ago
$190
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Sat, Aug 22 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $190 found 2 hours ago
Bargain Flight
Mon, May 18 - Wed, May 27
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$214 Roundtrip, found 1 day ago
$214
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Mon, May 18 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Wed, May 27, priced at $214 found 1 day ago
Bargain Flight
Wed, May 27 - Wed, Jun 3
CLT
Charlotte-Douglas Intl.
PWM
Portland Intl. Jetport
$238 Roundtrip, found 2 days ago
$238
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Wed, May 27 from Charlotte-Douglas Intl. to Portland Intl. Jetport, returning Wed, Jun 3, priced at $238 found 2 days ago