Book Exclusive Great Diamond Island Vacation Packages

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Great Diamond Island flight + hotel packages

River View Resort

River View Resort

2.5 out of 5
per person
Jun. 30 - Jul. 6
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
Stay at this motel in Bethel. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Sunday River and Bethel Chamber of Commerce are located nearby. Discover genuine guest reviews for River View Resort along with the latest prices and availability – book now.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
May 18 - May 24
Roundtrip non-stop flight included
Vancouver (YVR) to Portland (PWM)
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast. Our guests praise the breakfast and the bar in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby. Discover genuine guest reviews for Portland Harbor Hotel, in Downtown Portland neighborhood, along with the latest prices and availability – book now.
Inn By The Sea

Inn By The Sea

4 out of 5
per person
May 31 - Jun. 4
Roundtrip flight included
Edmonton (YEG) to Portland (PWM)
Stay at this 4-star beach hotel in Cape Elizabeth. Enjoy free valet parking, a beach locale, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby. Discover genuine guest reviews for Inn By The Sea along with the latest prices and availability – book now.
The Press Hotel, Marriott Autograph Collection

The Press Hotel, Marriott Autograph Collection

4 out of 5
Downtown Portland
per person
May 18 - May 24
Roundtrip non-stop flight included
Vancouver (YVR) to Portland (PWM)
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 2 bars/lounges, and breakfast. Our guests praise the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby. Discover genuine guest reviews for The Press Hotel, Marriott Autograph Collection, in Downtown Portland neighborhood, along with the latest prices and availability – book now.
USA Inn

USA Inn

2.5 out of 5
per person
Jun. 30 - Jul. 6
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
Stay at this motel in Wells. Enjoy free WiFi, free parking, and a beach shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Moody Beach and Ogunquit Beach are located nearby. Discover genuine guest reviews for USA Inn along with the latest prices and availability – book now.
Prices and availability subject to change. Additional terms may apply.

Top Great Diamond Island hotels deals

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
Free cancellation
Reserve now, pay when you stay
The price is CA $221 per night
CA $221
per night
Apr. 21 - Apr. 22
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast. Our guests praise the breakfast and the bar in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby. Discover genuine guest reviews for Portland Harbor Hotel, in Downtown Portland neighborhood, along with the latest prices and availability – book now.
Pet-friendly
Breakfast available
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St, Portland, ME
Free cancellation
Reserve now, pay when you stay
The price is CA $210 per night
CA $210
per night
May 12 - May 13
Stay at this spa hotel in Portland. Enjoy a full-service spa, breakfast, and WiFi. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby. Discover genuine guest reviews for The Westin Portland Harborview, in Downtown Portland neighborhood, along with the latest prices and availability – book now.
Pet-friendly
Spa
Casco Bay Hotel, Ascend Hotel Collection

Casco Bay Hotel, Ascend Hotel Collection

3.5 out of 5
80 John Roberts Rd., South Portland, ME
Free cancellation
Reserve now, pay when you stay
The price is CA $110 per night
CA $110
per night
Apr. 21 - Apr. 22
Stay at this 3.5-star 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. Discover genuine guest reviews for Casco Bay Hotel, Ascend Hotel Collection along with the latest prices and availability – book now.
Pet-friendly
Breakfast included
Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
9 Center Street, Portland, ME
Free cancellation
Reserve now, pay when you stay
The price is CA $258 per night
CA $258
per night
Apr. 21 - Apr. 22
Stay at this 4-star hotel in Portland. Enjoy free WiFi, 2 restaurants, and breakfast. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby. Discover genuine guest reviews for Canopy by Hilton Portland Waterfront, in Downtown Portland neighborhood, along with the latest prices and availability – book now.
Pet-friendly
Breakfast available
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
The price is CA $209 per night
CA $209
per night
Apr. 21 - Apr. 22
Stay at this 3.5-star spa hotel in Portland. Enjoy free WiFi, 2 bars/lounges, and a full-service spa. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby. Discover genuine guest reviews for Portland Regency Hotel & Spa, in Downtown Portland neighborhood, along with the latest prices and availability – book now.
Hot tub
Pet-friendly
La Quinta Inn & Suites by Wyndham Portland

La Quinta Inn & Suites by Wyndham Portland

2.5 out of 5
340 Park Ave, Portland, ME
Free cancellation
Reserve now, pay when you stay
The price is CA $135 per night
CA $135
per night
Apr. 21 - Apr. 22
Stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby. Discover genuine guest reviews for La Quinta Inn & Suites by Wyndham Portland along with the latest prices and availability – book now.
Pet-friendly
Pool
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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

Image for Portland Head Light

Portland Head Light

4.5/5(27 reviews)

Find out about the history of Cape Elizabeth with a stop at Portland Head Light. Stroll along the beautiful beaches or attend a sporting event in the area.

Portland Head Light
Image for LL Bean Flagship Store

LL Bean Flagship Store

4.5/5(50 reviews)

During your trip to Freeport, you can enjoy retail therapy at LL Bean Flagship Store. Stroll along the area's waterfront or simply enjoy its seafood restaurants.

LL Bean Flagship Store
Image for State Theatre

State Theatre

4.5/5(5 reviews)

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

State Theatre

Frequently asked questions

How much are vacation packages to Great Diamond Island?
With offers starting from as little as CA $1,206, hotel and flight packages are a fabulous way to stretch your travel budget. Great Diamond Island, here you come!
Where can I get the best vacation package deals for Great Diamond Island?
No matter how you travel, Travelocity can help you get the perfect Great Diamond Island package deal. The only thing you need to do is mix and match from our 400 air carriers and 665,000 worldwide properties.
Why should I purchase my Great Diamond Island vacation bundle via Travelocity?
We offer 24/7 support, high-quality service and a Price Match Guarantee. Life’s a great big journey — and we have exciting destinations for you to journey to in all four corners of the globe. Wander with us and your wallet will thank you for it.
Can I save on my Great Diamond Island car rental if I bundle it with a hotel or flight?
You sure can with our Great Diamond Island vacation packages. With one of these, there are tons of ways to stretch your budget further. Combine any two or more car, hotel, flight and tour bookings and watch your savings grow. With your own set of wheels, all the attractions around Great Diamond Island are just a road trip away.
What is the best time of year to go to Great Diamond Island?
You’ll be able to avoid the crowds and save money in , which are the quietest times for tourist visits. The high season months of are livelier and more expensive, but there’s likely to be more going on around Great Diamond Island. Book a hotel in and you’ll get the best value for your dollar. As a rule, room rates are dearer in .
Can I go on vacation to Great Diamond Island at this time?
Our team has all the local knowledge to help make your travel dreams come true, so before organizing your trip to Great Diamond Island, read through our Covid-19 Travel Advisor. This is where you can find all the latest info about quarantine policies, travel restrictions and a whole lot more.