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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 $472, price is now $411 per person
$411
per person
Dec 29 - Jan 3
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 breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
The Docent's Collection - New Opening

The Docent's Collection - New Opening

2 out of 5
Price was $717, price is now $595 per person
$595
per person
Dec 22 - Dec 24
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Popular attractions Thompson's Point and Maine Mall are located nearby.
Residence Inn Portland Downtown/Waterfront

Residence Inn Portland Downtown/Waterfront

3 out of 5
Price was $619, price is now $514 per person
$514
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this 3-star business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $1,174, price is now $1,000 per person
$1,000
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this 4.5-star 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 Wells Beach are located nearby.
84 Main

84 Main

4 out of 5
Price was $1,393, price is now $1,194 per person
$1,194
per person
Nov 29 - Dec 5
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this 4-star condo in Kennebunk. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Dock Square and Wells Beach are located nearby.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $734, price is now $639 per person
$639
per person
Dec 22 - Dec 24
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Stay at this 3.5-star B&B in Portland. Enjoy free breakfast, free WiFi, and concierge services. Popular attractions Thompson's Point and Maine Mall are located nearby.
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $691, price is now $609 per person
$609
per person
Dec 22 - Dec 24
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Stay at this 4-star 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.
Dormir

Dormir

3 out of 5
Price was $1,194, price is now $1,055 per person
$1,055
per person
Nov 29 - Dec 5
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this 3-star business-friendly hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Sebago Lake and Seacoast Adventure are located nearby.

Great Diamond Island Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
East Bayside
Price was $755, price is now $702 per person
$702
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $1,174, price is now $1,000 per person
$1,000
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
The Docent's Collection - New Opening

The Docent's Collection - New Opening

2 out of 5
Downtown Portland
Price was $1,242, price is now $1,110 per person
$1,110
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
AWOL Kennebunkport

AWOL Kennebunkport

3 out of 5
Price was $1,007, price is now $920 per person
$920
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)

Great Diamond Island Vacation Packages 5-7 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 $472, price is now $411 per person
$411
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Residence Inn Portland Downtown/Waterfront

Residence Inn Portland Downtown/Waterfront

3 out of 5
East Bayside
Price was $619, price is now $514 per person
$514
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
84 Main

84 Main

4 out of 5
Price was $1,393, price is now $1,194 per person
$1,194
per person
Nov 29 - Dec 5
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Dormir

Dormir

3 out of 5
Price was $1,194, price is now $1,055 per person
$1,055
per person
Nov 29 - Dec 5
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)

Top Flight Deals

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

Delta
Wed, Nov 12 - Sat, Nov 15
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$150 Roundtrip, found 4 days ago
$150
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Nov 12 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Sat, Nov 15, priced at $150 found 4 days ago
Breeze Airways
Wed, Nov 5 - Mon, Nov 10
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$175 Roundtrip, found 23 hours ago
$175
Roundtrip
found 23 hours ago
Select Breeze Airways flight, departing Wed, Nov 5 from Orlando Intl. to Portland Intl. Jetport, returning Mon, Nov 10, priced at $175 found 23 hours ago
United
Mon, Nov 3 - Thu, Nov 6
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$177 Roundtrip, found 5 days ago
$177
Roundtrip
found 5 days ago
Select United flight, departing Mon, Nov 3 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Thu, Nov 6, priced at $177 found 5 days ago
American Airlines
Thu, Jan 15 - Mon, Jan 19
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$189 Roundtrip, found 23 hours ago
$189
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Thu, Jan 15 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Mon, Jan 19, priced at $189 found 23 hours ago