Search Deals onGreat Diamond Island Vacation Packages
Photo by Robbie Martin
Great Diamond Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Airport/Maine Mall
per person
Jul 25 - Jul 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maine Mall and Thompson's Point are located nearby.
The Weldon Hotel
Save 100% on your flight
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Stay at this 4-star aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Thompson's Point and Maine Mall are located nearby.
Portland Harbor Hotel
Save 100% on your flight
per person
Jul 25 - Jul 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, 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.
AWOL Kennebunkport
Save 100% on your flight
per person
Jun 16 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Kansas City (MCI) to Portland (PWM)
Stay at this 3-star 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 Kennebunkport Village Green and W. Robert Paine Gallery are located nearby.
Inn at Diamond Cove
Save 100% on your flight
per person
Jul 25 - Jul 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Stay at this 3.5-star hotel in Portland. Enjoy free WiFi, 2 restaurants, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions Thompson's Point and Little Diamond Island are located nearby.
Microtel Inn & Suites By Wyndham Windham
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
The McKernan Inn
Save 100% on your flight
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Stay at this 3-star beach inn in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thompson's Point and Maine Mall are located nearby.
Blind Tiger Portland – Carleton Street
Save 100% on your flight
per person
Jul 25 - Jul 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Stay at this 3.5-star B&B in Portland. Enjoy free breakfast, free WiFi, and daily housekeeping. 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.
Great Diamond Island Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, May 7 - Wed, May 14
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$145 Roundtrip, found 5 days ago
$145
Roundtrip
found 5 days ago
Sat, Jul 5 - Tue, Jul 8
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$147 Roundtrip, found 1 day ago
$147
Roundtrip
found 1 day ago
Tue, Aug 5 - Tue, Aug 19
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Tue, Jul 1 - Wed, Sep 3
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$179 Roundtrip, found 6 days ago
$179
Roundtrip
found 6 days ago
Discover Other Travel Deals
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
Car Rentals in Great Diamond Island
- Car rentals in Portland
- Car rentals in Old Orchard Beach
- Car rentals in South Portland
- Car rentals in Scarborough
- Car rentals in Freeport
- Car rentals in Saco
- Car rentals in Cape Elizabeth
- Car rentals in Raymond
- Car rentals in Brunswick
- Car rentals in Biddeford
- Car rentals in Bath
- Car rentals in Phippsburg