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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.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Stay at this 3-star business-friendly hotel in Ogunquit. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ogunquit Beach and Moody Beach are located nearby.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Stay at this 4.5-star luxury resort in Cape Neddick. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Ogunquit Beach and Perkins Cove are located nearby.
River View Resort

River View Resort

2.5 out of 5
Save 100% on your flight
per person
Sep 21 - Sep 27
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Stay at this motel in Bethel. Enjoy free WiFi, free parking, and 4 outdoor pickleball courts. Our guests praise the helpful staff in our reviews. Popular attractions Sunday River and Bethel Pathway are located nearby.
Nonantum Resort

Nonantum Resort

3.5 out of 5
Save 100% on your flight
per person
Sep 21 - Sep 27
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Stay at this 3.5-star hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dock Square and Goose Rocks Beach are located nearby.
Chebeague Island Inn

Chebeague Island Inn

4 out of 5
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this 4-star beach hotel in Chebeague Island. Enjoy free WiFi, breakfast (surcharge), and a free ferry terminal shuttle. Popular attractions Little John Island Preserve and Winslow Memorial Park are located nearby.
InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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 Ogunquit Beach and Moody Beach are located nearby.
Microtel Inn & Suites by Wyndham York

Microtel Inn & Suites by Wyndham York

2 out of 5
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Book a stay at this business-friendly hotel in York. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Long Sands Beach and Short Sands Beach are located nearby.
Super 8 by Wyndham Portland ME

Super 8 by Wyndham Portland ME

2 out of 5
per person
Oct 9 - Oct 13
found 22 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Book a stay at this business-friendly motel in Westbrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.

Great Diamond Island Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Chebeague Island Inn

Chebeague Island Inn

4 out of 5
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Save 100% on your flight
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)
AWOL Kennebunkport

AWOL Kennebunkport

3 out of 5
Save 100% on your flight
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)

Great Diamond Island Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Nasons Corner
per person
Oct 4 - Oct 10
found 4 hours ago
Roundtrip flight included
Charlotte (CLT) to Portland (PWM)
Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
per person
Sep 21 - Sep 27
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
per person
Oct 4 - Oct 10
found 4 hours ago
Roundtrip flight included
Charlotte (CLT) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
per person
Sep 21 - Sep 27
found 21 hours ago
Roundtrip 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.

Frontier Airlines
Sat, Aug 16 - Sat, Aug 23
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Aug 16 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Aug 23, priced at $100 found 1 day ago
JetBlue Airways
Wed, Oct 15 - Sat, Oct 18
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Oct 15 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Sat, Oct 18, priced at $117 found 1 day ago
Delta
Tue, Sep 16 - Tue, Sep 30
LGA
LaGuardia
PWM
Portland Intl. Jetport
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 16 from LaGuardia to Portland Intl. Jetport, returning Tue, Sep 30, priced at $119 found 1 day ago
United
Tue, Sep 2 - Tue, Sep 9
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select United flight, departing Tue, Sep 2 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Tue, Sep 9, priced at $119 found 1 day ago