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Portland Vacation Packages

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Portland Flight + Hotel Packages

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

The Wolfeboro Inn

3.5 out of 5
Price was $506, price is now $396 per person
$396
per person
May 8 - May 10
found 15 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this beach hotel in Wolfeboro. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Lake Winnipesaukee and Hampshire Pewter Co. are located nearby.
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Price was $1,044, price is now $734 per person
$734
per person
May 12 - May 16
found 10 hours 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.
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Price was $1,079, price is now $772 per person
$772
per person
May 12 - May 16
found 10 hours 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.
84 Main

84 Main

4 out of 5
Price was $686, price is now $512 per person
$512
per person
Apr 11 - Apr 15
found 9 hours ago
Roundtrip flight included
Dallas (DAL) to Portland (PWM)
Stay at this condo in Kennebunk. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Dock Square and Kennebunk Free Library are located nearby.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $942, price is now $706 per person
$706
per person
May 12 - May 16
found 10 hours ago
Roundtrip non-stop 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 Cross Insurance Arena and Fore Street Gallery are located nearby.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $1,242, price is now $934 per person
$934
per person
May 12 - May 16
found 10 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.
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,248, price is now $959 per person
$959
per person
May 12 - May 16
found 10 hours ago
Roundtrip non-stop 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.
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Price was $746, price is now $592 per person
$592
per person
May 12 - May 16
found 10 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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 Vacation Packages 3-4 Night Stays

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

84 Main

4 out of 5
Price was $686, price is now $512 per person
$512
per person
Apr 11 - Apr 15
found 9 hours ago
Roundtrip flight included
Dallas (DAL) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $1,044, price is now $734 per person
$734
per person
May 12 - May 16
found 10 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
Price was $1,079, price is now $772 per person
$772
per person
May 12 - May 16
found 10 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $942, price is now $706 per person
$706
per person
May 12 - May 16
found 10 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)

Portland Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $855, price is now $629 per person
$629
per person
Apr 13 - Apr 18
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
84 Main

84 Main

4 out of 5
Price was $856, price is now $644 per person
$644
per person
Apr 13 - Apr 18
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
The McKernan Inn

The McKernan Inn

3 out of 5
Price was $1,499, price is now $1,133 per person
$1,133
per person
Apr 10 - Apr 17
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was $1,444, price is now $1,103 per person
$1,103
per person
Apr 10 - Apr 17
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)

Top Flight Deals

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

American Airlines
Wed, May 27 - Fri, Jun 5
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$183 Roundtrip, found 1 hour ago
$183
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Fri, Jun 5, priced at $183 found 1 hour ago
JetBlue Airways
Wed, Apr 15 - Mon, Apr 27
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$189 Roundtrip, found 2 days ago
$189
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Apr 15 from Tampa Intl. to Portland Intl. Jetport, returning Mon, Apr 27, priced at $189 found 2 days ago
JetBlue Airways
Tue, Apr 7 - Mon, Apr 13
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$235 Roundtrip, found 4 days ago
$235
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, Apr 7 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Mon, Apr 13, priced at $235 found 4 days ago
Bargain Flight
Wed, May 27 - Wed, Jun 3
CLT
Charlotte-Douglas Intl.
PWM
Portland Intl. Jetport
$238 Roundtrip, found 17 hours ago
$238
Roundtrip
found 17 hours 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 17 hours ago