Great Diamond Island Vacation Packages 2026 from $649

Great Diamond Island flight + hotel vacation packages

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

The Meadowmere Resort

$649

per person

Oct 3 - Oct 6

found 12 hours ago

Roundtrip flight included

Denver (DEN) to Portland (PWM)

2 hot tubs, an indoor pool, and a gym are all featured at this smoke-free hotel. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking. There's a restaurant and a bar/lounge for dining and drinks, and also a sauna on site.

Ogunquit River Inn & Suites

Moody

Save 100% on your flight

$959

per person

Sep 26 - Oct 3

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Portland (PWM)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. There's a seasonal outdoor pool on site, and a terrace and a garden are also provided.

Blind Tiger Portland - Danforth Street.

West End

$762

per person

Nov 13 - Nov 15

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Portland (PWM)

This bed & breakfast features free WiFi in public areas, concierge services, and self parking. Enjoy the free self-serve breakfast each morning. Luggage storage is also provided.

Inn By The Sea

Save 100% on your flight

$1,366

per person

Nov 3 - Nov 10

found 17 hours ago

Roundtrip non-stop flight included

Memphis (MEM) to Portland (PWM)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Families will appreciate the playground, onsite laundry facilities, and free supervised childcare. Enjoy the outdoor pool and perks like free valet parking.

Newagen Seaside Inn

$846

per person

Sep 27 - Oct 2

found 18 hours ago

Roundtrip flight included

Minneapolis (MSP) to Portland (PWM)

This hotel features 2 outdoor tennis courts, an outdoor pool, and a restaurant. Bring the family and enjoy the bowling alley, arcade/game room, and kid-friendly dining. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi.

Top Great Diamond Island hotels deals

Clarion Pointe South Portland

675 Main Street I-95 South Portland ME

Free Cancellation

$77 nightly

$83 total

Sep 2 - Sep 3

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and WiFi in public areas. Enjoy the indoor pool and free perks like continental breakfast and free self parking.

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Free Cancellation

$131 nightly

$145 total

Sep 1 - Sep 2

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the hot tub and perks like free self parking and a free cruise terminal shuttle.

Quality Inn & Suites South Portland

738 Main Street South Portland ME

Free Cancellation

$86 nightly

$94 total

Aug 23 - Aug 24

Total with taxes and fees

This hotel features free WiFi in public areas, free newspapers, and free self parking. Enjoy the free continental breakfast each morning. A garden and a picnic area are also provided.

Waves Oceanfront Resort

87 W Grand Ave Old Orchard Beach ME

$160 nightly

$174 total

Sep 13 - Sep 14

Total with taxes and fees

This hotel features an outdoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A coffee shop, a lobby fireplace, and a picnic area are also on offer.

Portland Regency Hotel & Spa

20 Milk Street Portland ME

Free Cancellation

Reserve now, pay when you stay

$316 nightly

$350 total

Aug 30 - Aug 31

Total with taxes and fees

A full-service spa, a hot tub, and a restaurant are all featured at this smoke-free hotel. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and a roundtrip airport shuttle. There's a gym on site, and laundry facilities and concierge services are also offered.

Fireside Inn & Suites Portland

81 Riverside St Portland ME

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$110 total

Sep 8 - Sep 9

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much are vacation packages to Great Diamond Island?

Exciting adventures await you in Great Diamond Island, with Travelocity vacation packages starting from just $649. Including hotels and flights, these amazing deals make it easy to experience more of our wonderful planet.

Where can I get the best vacation package deals for Great Diamond Island?

With at least 400 partner airlines and 1,000,000 properties all over the world, you can't go wrong with Travelocity. Scroll through our comprehensive range and score an incredible Great Diamond Island package deal. Isn't it amazing when vacation planning is that easy?

Why should I purchase my Great Diamond Island vacation package with Travelocity?

Whether you're planning a month-long vacation or a last-minute trip, we have plenty of amazing destinations to choose from at a good price. In addition, we provide round-the-clock support, top-notch service and a Price Match Guarantee. Save yourself the effort and time and lock in your dream vacation today.

Can I save money on my Great Diamond Island car rental if I combine it with my hotel or flight?

You certainly can with our Great Diamond Island vacation packages. With one of these, there are loads of ways to make your travel budget go further. Bundle any two or more car, flight, hotel and tour bookings and see the savings grow. With a rental car, all the landmarks in and around Great Diamond Island are an unforgettable road trip away.