Great Diamond Island Holidays from £1,263

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Top Great Diamond Island Flight + Hotel Deals

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

Saco Bay Hotel

2.5 out of 5
Price was £1,604, price is now £1,263 per person
£1,263
per person
1 Jul - 7 Jul
found 1 day ago
Return direct flight included
London (LON) to Portland (PWM)
7.6/10 Good! (1,050 reviews)
Great place to stay for AAU basketball in the area.

Reviewed on 1 May 2026

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was £2,431, price is now £1,966 per person
£1,966
per person
1 Jul - 7 Jul
found 1 day ago
Return direct flight included
London (LON) to Portland (PWM)
9.6/10 Exceptional! (300 reviews)
Super easy to find, the apartment was very clean, the complimentary water and coffee were excellent! We loved our stay!!

Reviewed on 26 Apr 2026

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was £2,474, price is now £2,071 per person
£2,071
per person
1 Jul - 7 Jul
found 1 day ago
Return direct flight included
London (LON) to Portland (PWM)
9.8/10 Exceptional! (100 reviews)
Lovely suite! Comfy king bed, everything spotless, Great location. Would stay here again

Reviewed on 23 Apr 2026

The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

2 out of 5
Downtown Portland
Price was £2,583, price is now £2,174 per person
£2,174
per person
1 Jul - 7 Jul
found 1 day ago
Return direct flight included
London (LON) to Portland (PWM)
9.6/10 Exceptional! (10 reviews)
So lovely to be in a space big enough for four that felt more like “home” than hotel. Great location in Old Port. Friendly, responsive staff. Comfy beds. Amazing high ceilings and aesthetically minimalist. Looking forward to another stay.

Reviewed on 24 Apr 2026

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was £1,938, price is now £1,662 per person
£1,662
per person
1 Jul - 7 Jul
found 1 day ago
Return direct flight included
London (LON) to Portland (PWM)
9.4/10 Exceptional! (1,633 reviews)
Enjoyed the hotel for a long weekend. Room was clean and very convenient. Fitness room and spa were nice additions. Staff very friendly, courteous, and prompt. Terrific location for navigating Portland. Would definitely stay again and recommend.

Reviewed on 29 Apr 2026

Great Diamond Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)

Top hotels in Great Diamond Island

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is £158 per night from 3 May to 4 May
£158
3 May - 4 May
includes taxes & fees
9.2/10 Wonderful! (1,755 reviews)
We (and our kids!) loved the “pantry” on each floor — fruit, snacks, cookies, tea, coffee. It was a much-appreciated surprise. Room was clean and quiet, and all staff were friendly and helpful.

Reviewed on 29 Apr 2026

Portland Harbor Hotel
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundable
The price is £141 per night from 3 May to 4 May
£141
3 May - 4 May
includes taxes & fees
9.4/10 Exceptional! (1,200 reviews)
First day my room wasn't cleaned ! Thought I'd get some complimentary water , but only had for first night !

Reviewed on 1 May 2026

Cambria Hotel Portland Downtown-Old Port
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
The price is £129 per night from 26 May to 27 May
£129
26 May - 27 May
includes taxes & fees
9.4/10 Exceptional! (1,641 reviews)
The room was great. No microwave (which would have been helpful)

Reviewed on 30 Apr 2026

Portland Regency Hotel & Spa
See all 2,352 properties in Great Diamond Island
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

East End Beach

East End Beach

Swim in the Atlantic Ocean, stroll along the sand-and-pebble shoreline or enjoy a picnic with unbeatable views at Portland’s public beach.

East End Beach

Portland Exposition Building

Learn about the events happening in Portland Exposition Building during your trip to Portland. Experience the area's entertainment choices and great live music.

Portland Exposition Building

International Cryptozoology Museum

You can spend time studying the exhibits at International Cryptozoology Museum during your trip to Portland. Stroll along the area's waterfront or experience its acclaimed theatre scene.

International Cryptozoology Museum

What to do in Great Diamond Island

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

£7
per traveller
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

£11
per traveller
Portland Smartphone Audio Tour: Self-Guided Drive
Self-Guided Driving & Walking Bundle of Portland Maine Tours

Portland Maine App-Based Driving & Walking Audio Tour Bundle

£17
per traveller
Portland Maine App-Based Driving & Walking Audio Tour Bundle
See all activities in Great Diamond Island

Frequently asked questions

Can I cancel my flight booking to Great Diamond Island due to COVID-19?
If you've yet to book your tickets, scan the terms and conditions of your preferred airline. If you've already locked in your flight to Great Diamond Island, visit our Customer Service Portal. The information here will help you work out which COVID-19 policies are applicable to your reservation and advise the next steps.
What's the best way to find cheap flights to Great Diamond Island that have flexible change policies?
By using our neat "No change fee" filter, that's how. Just type in your travel dates, click "Search," then tick the checkbox under the "Flexible change policies" heading (it's on the top left of your screen). Expedia makes it a cinch to find flexible, low-priced tickets to Great Diamond Island.
What are some of the general tips for travellers to Great Diamond Island during the COVID-19 outbreak?
As a result of COVID-19, travelling today comes with more challenges. Have a read over these valuable tips before jumping on your flight to Great Diamond Island:
  • Before you lock in a flight, see if any travel restrictions apply — in both your destination and origin. Keep informed with the latest updates by checking government travel advisories.
  • Wear a face mask even during airport screening. A TSA employee will ask you to temporarily lower your mask for identification purposes.
  • Avoid handing your boarding pass directly to a TSA employee. Rather, you should position the pass on the reader and then hold it up for inspection.
  • TSA is now allowing passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on luggage. This will have to be removed from your bag and presented for screening.
  • To minimize handling during screening, place personal items such as your phone, coins and keys into your carry-on rather than into the bins.
  • Transport your food items in a clear plastic bag and also put them in a screening bin. Keeping food separate from your carry-on makes it less likely that a TSA agent will need to open your bag for inspection.

Which airlines fly to Great Diamond Island?
Southwest Airlines operates flights into or near Great Diamond Island, including 182 that touch down at Portland Intl. Jetport Airport (PWM) each month. Pick your holiday dates and then book your seat early for an unbeatable deal.
How can I find cheap tickets to Great Diamond Island?
One of the easiest ways to score cheap tickets to Great Diamond Island is to be flexible with your travel dates. Search for your flights, then click "flexible dates" above the results. It'll bring up the cheapest prices for nearby days. The best price for a flight to Great Diamond Island in the last seven days was . Booking ahead of time will usually help you pick up an even bigger bargain.
How much is a flight to Great Diamond Island?
One-way flights departing from () sold for just in the last seven days. During this time, the cost of a return ticket to Great Diamond Island varied between and . If you spot a bargain ticket, book ASAP — these fares don't wait around for long.
What are the most popular airports to fly into in Great Diamond Island?
Start arranging your Great Diamond Island adventure by reserving a seat on one of the 1571 flights every month to Portland Intl. Jetport Airport (PWM). This is the region's main point of entry.
When is the cheapest time to fly to Great Diamond Island?
Take off to Great Diamond Island early on in the week and you'll usually be rewarded with lower-cost fares. Tuesday is known for being the cheapest day to hop on a plane, closely followed by Monday. If you're eager to avoid the priciest flights, give Saturdays a wide berth.
How much is a plane ticket to Great Diamond Island?
In the last seven days, ticket prices to Great Diamond Island ranged from to .
Which airlines with flights to Great Diamond Island employ COVID-19 cleanliness policies?
In response to the global COVID-19 pandemic, many airlines have adopted additional actions and measures to help travellers get back in the skies. These carriers include:
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.