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Great Diamond Island Vacation Packages

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Great Diamond Island 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 $565, price is now $497 per person
$497
per person
Mar 25 - Mar 28
found 8 hours ago
Roundtrip non-stop flight included
Dallas (DAL) 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.
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Price was $773, price is now $585 per person
$585
per person
Mar 25 - Mar 28
found 8 hours ago
Roundtrip non-stop flight included
Dallas (DAL) 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 McKernan Inn

The McKernan Inn

3 out of 5
Price was $717, price is now $565 per person
$565
per person
Mar 25 - Mar 28
found 8 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
Book a stay at this beach inn in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Fort Preble and Portland Harbor Museum are located nearby.
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Price was $714, price is now $578 per person
$578
per person
Mar 25 - Mar 28
found 8 hours ago
Roundtrip non-stop flight included
Dallas (DAL) 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.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $665, price is now $538 per person
$538
per person
Mar 25 - Mar 28
found 8 hours ago
Roundtrip non-stop flight included
Dallas (DAL) 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 $780, price is now $641 per person
$641
per person
Mar 25 - Mar 28
found 8 hours ago
Roundtrip non-stop flight included
Dallas (DAL) 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.
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Price was $633, price is now $527 per person
$527
per person
Mar 25 - Mar 28
found 8 hours ago
Roundtrip non-stop flight included
Dallas (DAL) 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
Price was $889, price is now $748 per person
$748
per person
Mar 25 - Mar 28
found 8 hours ago
Roundtrip non-stop flight included
Dallas (DAL) 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.

Great Diamond Island 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 $665, price is now $538 per person
$538
per person
Mar 25 - Mar 28
found 8 hours ago
Roundtrip non-stop 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 $773, price is now $585 per person
$585
per person
Mar 25 - Mar 28
found 8 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
The McKernan Inn

The McKernan Inn

3 out of 5
Price was $717, price is now $565 per person
$565
per person
Mar 25 - Mar 28
found 8 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was $714, price is now $578 per person
$578
per person
Mar 25 - Mar 28
found 8 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)

Great Diamond Island Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Freeport/Brunswick

Hampton Inn Freeport/Brunswick

2.5 out of 5
Price was $1,117, price is now $1,097 per person
$1,097
per person
May 5 - May 10
found 23 hours ago
Roundtrip non-stop flight included
St. Louis (STL) to Portland (PWM)
Residence Inn Bath Brunswick Area

Residence Inn Bath Brunswick Area

3 out of 5
Price was $1,209, price is now $1,181 per person
$1,181
per person
May 5 - May 10
found 23 hours ago
Roundtrip non-stop flight included
St. Louis (STL) to Portland (PWM)
SpringHill Suites by Marriott Freeport Brunswick

SpringHill Suites by Marriott Freeport Brunswick

2 out of 5
Price was $1,138, price is now $1,113 per person
$1,113
per person
May 5 - May 10
found 23 hours ago
Roundtrip non-stop flight included
St. Louis (STL) to Portland (PWM)
Hampton Inn Bath (Brunswick Area)

Hampton Inn Bath (Brunswick Area)

3 out of 5
Price was $1,167, price is now $1,143 per person
$1,143
per person
May 5 - May 10
found 23 hours ago
Roundtrip non-stop flight included
St. Louis (STL) to Portland (PWM)

Top Flight Deals

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

Breeze Airways
Wed, May 27 - Fri, Jun 5
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$175 Roundtrip, found 5 hours ago
$175
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Fri, Jun 5, priced at $175 found 5 hours ago
Bargain Flight
Mon, May 18 - Wed, May 27
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$203 Roundtrip, found 4 days ago
$203
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Mon, May 18 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Wed, May 27, priced at $203 found 4 days ago
Delta
Fri, Mar 6 - Wed, Mar 11
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$209 Roundtrip, found 4 days ago
$209
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Mar 6 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Wed, Mar 11, priced at $209 found 4 days ago
American Airlines
Tue, Mar 17 - Wed, Mar 25
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$219 Roundtrip, found 3 days ago
$219
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Mar 17 from Tampa Intl. to Portland Intl. Jetport, returning Wed, Mar 25, priced at $219 found 3 days ago