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.
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Nasons Corner
per person
Oct 2 - Oct 5
found 15 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)
2 hot tubs, an indoor pool, and a gym are all featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy a meal from the a restaurant and perks like free self parking.
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Save 100% on your flight
per person
Oct 23 - Oct 27
found 15 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)
This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free local cuisine breakfast each morning. A terrace and a garden are also provided.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
per person
Sep 23 - Sep 27
found 18 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)
A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center, laundry service, and valet parking. Relax with a drink at one of the 2 poolside bars and enjoy perks like free self parking.
Chebeague Island Inn

Chebeague Island Inn

4 out of 5
per person
Sep 15 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate perks like free WiFi and a free ferry terminal shuttle. A garden, a lobby fireplace, and a picnic area are also on offer.
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
per person
Oct 2 - Oct 5
found 15 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) 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.

Top Great Diamond Island hotels deals

Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $120 total per night
$120 total
Aug 24 - Aug 25
Total includes taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Free Cancellation
Reserve now, pay when you stay
$152 nightly
The price is $168 total per night
$168 total
Aug 11 - Aug 12
Total includes 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
Comfort Inn Airport

Comfort Inn Airport

2.5 out of 5
90 Maine Mall Rd, South Portland, ME
Free Cancellation
Reserve now, pay when you stay
$134 nightly
The price is $146 total per night
$146 total
Sep 1 - Sep 2
Total includes 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
Germaine Inn South Portland

Germaine Inn South Portland

2 out of 5
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Free Cancellation
$90 nightly
The price is $98 total per night
$98 total
Aug 7 - Aug 8
Total includes 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
Casco Bay Hotel Portland Airport - Maine Mall, Ascend Hotel Collection

Casco Bay Hotel Portland Airport - Maine Mall, Ascend Hotel Collection

3.5 out of 5
80 John Roberts Rd., South Portland, ME
Free Cancellation
Reserve now, pay when you stay
$161 nightly
The price is $175 total per night
$175 total
Aug 19 - Aug 20
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free self parking, and a free airport shuttle. Business travelers can take advantage of the free WiFi in public areas. There's a gym on site, and a 24-hour front desk and dry cleaning are also provided.
Breakfast included
Free airport shuttle
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Free Cancellation
Reserve now, pay when you stay
$136 nightly
The price is $150 total per night
$150 total
Sep 1 - Sep 2
Total includes taxes and fees
2 hot tubs, an indoor pool, and a gym are all featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy a meal from the a restaurant and perks like free self parking.
Pool
Hot Tub
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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.

Popular places to visit

State Theatre showing street scenes as well as an individual femail

State Theatre

4.5/5(88 reviews)

You can make plans for a show at State Theatre during your trip to Portland. Experience the area's entertainment choices and acclaimed theater scene.

State Theatre
Portland Museum of Art showing art and interior views as well as a small group of people

Portland Museum of Art

4.5/5(255 reviews)

Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.

Portland Museum of Art
East End Beach which includes general coastal views and a beach as well as a small group of people

East End Beach

If a restful vacation is part of your travel plans, East End Beach might be the perfect place to seek out during your trip to Portland.

East End Beach

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 $572. 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

Photo by Robbie Martin
Photo by Robbie Martin