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.
84 Main

84 Main

4 out of 5
Price was $720, price is now $574 per person
$574
per person
Nov 20 - Nov 23
just found
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
Stay at this condo in Kennebunk. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Dock Square and Wells Beach are located nearby.
The property was very spacious, well equipped, and well taken care of. There was lots of natural light and a very large outdoor deck accessible from all bedrooms and the living room.

Reviewed on Jul 17, 2026

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Price was $1,394, price is now $1,083 per person
$1,083
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions Thompson's Point and Portland Head Light are located nearby.

Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,323, price is now $1,069 per person
$1,069
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $1,738, price is now $1,405 per person
$1,405
per person
Nov 4 - Nov 8
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions Thompson's Point and Portland Head Light are located nearby.
Place was charming and quirky. Very comfortable and well located.

Reviewed on Sep 18, 2026

Evalina Hotel

Evalina Hotel

2.5 out of 5
Price was $1,250, price is now $1,013 per person
$1,013
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
Better than expected. This new property was in a great location. Easy to walk to restaurants and shopping. Comfortable bed, nice bathroom and a sitting area with sofa, chair and tv. I was a little concerned because we could hear music from a nearby bar, but everything stopped by 10 o’clock. Would return.

Reviewed on Sep 25, 2026

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
Price was $924, price is now $749 per person
$749
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and daily housekeeping. Popular attractions Thompson's Point and Maine Mall are located nearby.
Beautiful place

Reviewed on Sep 20, 2026

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Price was $944, price is now $772 per person
$772
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Cross Insurance Arena and Maine Mall are located nearby.

The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

3.5 out of 5
Price was $936, price is now $768 per person
$768
per person
Oct 30 - Nov 1
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 Cross Insurance Arena and Thompson's Point are located nearby.
This loft was perfect! We will be back and stay longer!!

Reviewed on Sep 25, 2026

Great Diamond Island 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 $720, price is now $574 per person
$574
per person
Nov 20 - Nov 23
just found
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $1,738, price is now $1,405 per person
$1,405
per person
Nov 4 - Nov 8
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Price was $1,250, price is now $1,013 per person
$1,013
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
The Kendall Inn

The Kendall Inn

3.5 out of 5
Price was $765, price is now $640 per person
$640
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop 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.
Inn at St John Portland In-Town

Inn at St John Portland In-Town

2.5 out of 5
Valley Street
Price was $550, price is now $407 per person
$407
per person
Dec 11 - Dec 16
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,176, price is now $732 per person
$732
per person
Dec 11 - Dec 16
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,256, price is now $875 per person
$875
per person
Dec 11 - Dec 16
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $759, price is now $547 per person
$547
per person
Dec 11 - Dec 16
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)

Top Flight Deals

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

Breeze Airways
Sat, Nov 7 - Sat, Nov 14
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$144 Roundtrip, found 5 hours ago
$144
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Sat, Nov 7 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Nov 14, priced at $144 found 5 hours ago
Breeze Airways
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$185 Roundtrip, found 6 hours ago
$185
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Wed, Oct 28 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Oct 31, priced at $185 found 6 hours ago
Breeze Airways
Wed, Nov 11 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$213 Roundtrip, found 13 hours ago
$213
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Wed, Nov 11 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Dec 2, priced at $213 found 13 hours ago
Delta
Tue, Oct 20 - Sat, Oct 31
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$301 Roundtrip, found 3 days ago
$301
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Oct 20 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Sat, Oct 31, priced at $301 found 3 days ago