Search Deals on
Great Diamond Island Vacation Packages

Build your package with 2 more options

Great Diamond Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Saco Bay Hotel - Saco / Old Orchard Beach

Saco Bay Hotel - Saco / Old Orchard Beach

2.5 out of 5
Price was $766, price is now $731 per person
$731
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this business-friendly hotel in Saco. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Old Orchard Beach and Saco Museum are located nearby.
We stayed for the weekend it was very clean. Close to most of the attractions. The staff was friendly. Enjoyed the stay.

Reviewed on Nov 10, 2026

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $1,485, price is now $1,201 per person
$1,201
per person
Dec 31 - Jan 5
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this luxury hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dock Square and Kennebunkport Village Green are located nearby.
Amazing place for our Mini Moon! Would definitely recommend

Reviewed on Nov 13, 2026

Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,401, price is now $1,194 per person
$1,194
per person
Dec 31 - Jan 5
found 23 hours 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 breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Price was $1,336, price is now $1,168 per person
$1,168
per person
Dec 31 - Jan 5
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Thompson's Point are located nearby.
We highly enjoyed our stay here! Great restaurant downstairs, very clean, and helpful kind staff! Wish we could stay longer!

Reviewed on Nov 12, 2026

InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
Price was $974, price is now $865 per person
$865
per person
Dec 28 - Jan 3
found 12 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) to Portland (PWM)
Stay at this motel in Ogunquit. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Footbridge Beach and Ogunquit Beach are located nearby.

The Kendall Inn

The Kendall Inn

3.5 out of 5
Price was $965, price is now $860 per person
$860
per person
Dec 31 - Jan 5
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this B&B in Freeport. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LL Bean Flagship Store and Freeport Historical Society are located nearby.

The Kennebunk Inn

The Kennebunk Inn

2.5 out of 5
Price was $878, price is now $831 per person
$831
per person
Dec 31 - Jan 5
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.

Purity Spring Resort

Purity Spring Resort

2 out of 5
Price was $772, price is now $741 per person
$741
per person
Jan 15 - Jan 19
found 16 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this ski hotel in Madison. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions King Pine Ski Area and Crystal Lake are located nearby.
The staff is as wonderful as the location, ok better!! Customer care at its finest.

Reviewed on Nov 7, 2026

Great Diamond Island Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Saco Bay Hotel - Saco / Old Orchard Beach

Saco Bay Hotel - Saco / Old Orchard Beach

2.5 out of 5
Price was $766, price is now $731 per person
$731
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $1,099, price is now $935 per person
$935
per person
Dec 28 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,421, price is now $1,321 per person
$1,321
per person
Dec 28 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)
Purity Spring Resort

Purity Spring Resort

2 out of 5
Price was $772, price is now $741 per person
$741
per person
Jan 15 - Jan 19
found 16 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)

Great Diamond Island 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
Price was $1,141, price is now $964 per person
$964
per person
Dec 22 - Dec 28
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Price was $1,583, price is now $1,251 per person
$1,251
per person
Dec 22 - Dec 28
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $1,485, price is now $1,201 per person
$1,201
per person
Dec 31 - Jan 5
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,401, price is now $1,194 per person
$1,194
per person
Dec 31 - Jan 5
found 23 hours ago
Roundtrip 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
Mon, Feb 15 - Sat, Feb 20
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$224 Roundtrip, found 1 hour ago
$224
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Mon, Feb 15 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Feb 20, priced at $224 found 1 hour ago
Breeze Airways
Wed, Feb 24 - Sat, Feb 27
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$256 Roundtrip, just found
$256
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Feb 24 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Feb 27, priced at $256 just found
Delta
Sun, Feb 28 - Wed, Mar 10
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$267 Roundtrip, found 18 hours ago
$267
Roundtrip
found 18 hours ago
Select Delta flight, departing Sun, Feb 28 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Wed, Mar 10, priced at $267 found 18 hours ago
American Airlines
Sat, Dec 5 - Tue, Dec 8
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$277 Roundtrip, found 2 days ago
$277
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Dec 5 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Tue, Dec 8, priced at $277 found 2 days ago