Deals on vacations and trips to Great Diamond Island

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Great Diamond Island flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
Price was $1,270, price is now $878 per person
$878
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
A marina, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Make the most of the gym and outdoor tennis court, and relax with drinks at one of the 3 bars/lounges.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Save 100% on your flight
Price was $1,727, price is now $1,190 per person
$1,190
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) 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.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $1,671, price is now $1,182 per person
$1,182
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $6,437, price is now $4,585 per person
$4,585
per person
Sep 8 - Sep 13
found 16 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) 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.
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $1,850, price is now $1,385 per person
$1,385
per person
Sep 8 - Sep 13
found 16 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) 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.

Top Great Diamond Island hotels deals

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
340 Park Ave Portland ME
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $165 total per night
$165 total
Jul 5 - Jul 6
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the free on-the-go breakfast each morning.
Pool
Breakfast included
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Free Cancellation
Reserve now, pay when you stay
$331 nightly
The price is $366 total per night
$366 total
Jul 5 - Jul 6
Total with taxes and fees
This hotel features 3 coffee shops/cafes and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll find a restaurant and a bar/lounge onsite for dining and drinks, along with a 24-hour front desk.
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Free Cancellation
$256 nightly
The price is $283 total per night
$283 total
Jul 5 - Jul 6
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A safe deposit box is provided and the front desk is staffed around-the-clock.
Pet friendly
Free WiFi
Clarion Pointe South Portland

Clarion Pointe South Portland

2 out of 5
675 Main Street I-95 South Portland ME
Free Cancellation
$99 nightly
The price is $108 total per night
$108 total
Jul 20 - Jul 21
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
Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

2.5 out of 5
90 Maine Mall Rd South Portland ME
Free Cancellation
$120 nightly
The price is $131 total per night
$131 total
Jul 5 - Jul 6
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.
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Free Cancellation
Reserve now, pay when you stay
$289 nightly
The price is $320 total per night
$320 total
Jul 5 - Jul 6
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.
Hot Tub
Spa
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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 $878. 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.

Photos of local treasures

Browse Great Diamond Island vacation photos for more inspiration

A calm sea with a sailboat and rocky coastline.
A house with a red roof on stilts over water, surrounded by trees and a grassy hill.
A large house with a red roof and a wooden dock extending into a body of water.
A dock with a small building, people, and colorful items.

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