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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 Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Price was $586, price is now $439 per person
$439
per person
Mar 20 - Mar 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Portland Stage are located nearby.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Save 100% on your flight
Price was $698, price is now $460 per person
$460
per person
Feb 26 - Mar 4
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 Cross Insurance Arena and Fore Street Gallery are located nearby.
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Save 100% on your flight
Price was $717, price is now $489 per person
$489
per person
Feb 26 - Mar 4
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions N.W. Barrett Gallery and Fore Street Gallery are located nearby.
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $1,549, price is now $1,101 per person
$1,101
per person
Feb 26 - Mar 4
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Price was $757, price is now $544 per person
$544
per person
Mar 20 - Mar 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $880, price is now $678 per person
$678
per person
Feb 1 - Feb 6
found 12 hours ago
Roundtrip flight included
New York (JFK) 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
Price was $1,337, price is now $1,033 per person
$1,033
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Hilton Garden Inn Freeport Downtown

Hilton Garden Inn Freeport Downtown

3 out of 5
Save 100% on your flight
Price was $986, price is now $764 per person
$764
per person
Feb 26 - Mar 4
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this business-friendly hotel in Freeport. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions LL Bean Flagship Store and Freeport Historical Society are located nearby.

Freeport Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Downtown Portland
Price was $586, price is now $439 per person
$439
per person
Mar 20 - Mar 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $757, price is now $544 per person
$544
per person
Mar 20 - Mar 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $632, price is now $463 per person
$463
per person
Mar 20 - Mar 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was $654, price is now $489 per person
$489
per person
Mar 20 - Mar 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 $698, price is now $460 per person
$460
per person
Feb 26 - Mar 4
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $705, price is now $477 per person
$477
per person
Feb 1 - Feb 6
found 12 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $717, price is now $489 per person
$489
per person
Feb 26 - Mar 4
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $1,549, price is now $1,101 per person
$1,101
per person
Feb 26 - Mar 4
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)

Top Flight Deals

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

Breeze Airways
Mon, Jan 5 - Fri, Jan 9
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$170 Roundtrip, found 1 day ago
$170
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Jan 5 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Fri, Jan 9, priced at $170 found 1 day ago
Breeze Airways
Mon, Dec 29 - Wed, Jan 7
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$173 Roundtrip, found 6 hours ago
$173
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Mon, Dec 29 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Jan 7, priced at $173 found 6 hours ago
Bargain Flight
Tue, Jan 20 - Sat, Jan 24
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$184 Roundtrip, found 1 day ago
$184
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Jan 20 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Sat, Jan 24, priced at $184 found 1 day ago
Breeze Airways
Fri, Feb 6 - Sun, Feb 8
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$251 Roundtrip, found 20 hours ago
$251
Roundtrip
found 20 hours ago
Select Breeze Airways flight, departing Fri, Feb 6 from Tampa Intl. to Portland Intl. Jetport, returning Sun, Feb 8, priced at $251 found 20 hours ago