Great Diamond Island Vacation Packages 2026 from $664

Great Diamond Island flight + hotel vacation packages

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

The Meadowmere Resort

$664

per person

Oct 14 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Minneapolis (MSP) 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.

Blind Tiger Portland - Danforth Street.

West End

Save 100% on your flight

$2,076

per person

Oct 19 - Oct 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Ogunquit River Inn & Suites

Moody

$823

per person

Oct 19 - Oct 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Evalina Hotel

Downtown Portland

Save 100% on your flight

$1,746

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Portland (PWM)

Free WiFi in public areas is available at this aparthotel. Take advantage of the self parking.

Blind Tiger Portland – Carleton Street

West End

Save 100% on your flight

$1,653

per person

Sep 27 - Oct 2

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Portland (PWM)

Free WiFi in public areas, a terrace, and a garden are available at this bed & breakfast. Enjoy the free on-the-go breakfast each morning. Concierge services are provided for your convenience.

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 1 - Sep 2

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.

Pool

Breakfast included

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.

Pool

Hot Tub

Quality Inn & Suites South Portland

738 Main Street South Portland ME

Free Cancellation

$86 nightly

$93 total

Sep 9 - Sep 10

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.

Breakfast included

Pet friendly

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.

Pool

Hot Tub

Fireside Inn & Suites Portland

81 Riverside St Portland ME

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$108 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.

Pool

Hot Tub

Comfort Inn South Portland Airport

90 Maine Mall Rd South Portland ME

Free Cancellation

$115 nightly

$125 total

Sep 7 - Sep 8

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and a free airport shuttle. Traveling on business? Take advantage of the express check-out, laundry service, and free train station pick-up. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Free airport shuttle

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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 $664. 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.