Cundys Harbor Holidays from £1,418

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Your Cundys Harbour Holiday

With all your travel needs organised before you go, our Cundys Harbour holiday packages mean you can focus more on having a good time! One neighbourhood to consider staying in this interesting city is Harpswell, which is great for nature and culture. Make your trip to Cundys Harbour even more exciting by including some sightseeing. Bailey Island Bridge, Ragged Island and Paddleworks are some of the major attractions you'll want to explore. Stop daydreaming and start adventuring. Check out the broad range of options on Expedia today and put your Cundys Harbour holiday plans into action!

Top Cundys Harbor Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
1802 House Bed and Breakfast

1802 House Bed and Breakfast

3.5 out of 5
Price was £1,603, price is now £1,418 per person
£1,418
per person
26 Sept - 30 Sept
found 21 hours ago
Return flight included
Aberdeen (ABZ) to Portland (PWM)
9.8/10 Exceptional! (117 reviews)
Superb location. Easy and beautiful walk to downtown to avoid all the parking hassle there. Staff is out of this world and the breakfast, we want to go back just for that!!!

Reviewed on 29 Jun 2026

Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Price was £2,048, price is now £1,654 per person
£1,654
per person
26 Sept - 30 Sept
found 21 hours ago
Return flight included
Aberdeen (ABZ) to Portland (PWM)
10/10 Exceptional! (5 reviews)
It was a spacious, clean, well thought out space with all the expected amenities. The location is ideal, and the hotel is truly a treasure.

Reviewed on 28 Jun 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 £1,636, price is now £1,454 per person
£1,454
per person
26 Sept - 30 Sept
found 21 hours ago
Return flight included
Aberdeen (ABZ) to Portland (PWM)
9.6/10 Exceptional! (345 reviews)
The room was very clean. The kitchen was well stocked with a few minor exceptions, namely no cutting boards (small thing). The location is perfect for exploring Old Town, highly recommend. The only improvement I would request would be some small fans in the rooms as the meager HVAC couldn't really circulate the air and it got a bit stale during the night. Very minor comfort issue. We will definitely consider staying with Docent again.

Reviewed on 9 Jul 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was £1,704, price is now £1,554 per person
£1,554
per person
26 Sept - 30 Sept
found 21 hours ago
Return flight included
Aberdeen (ABZ) to Portland (PWM)
9.4/10 Exceptional! (1,775 reviews)
Only 4 rooms that were having A/C problems. Of course we had one the rooms. If the A/C isn’t working, why continue to reserve the rooms and not just fix the A/C??? Front desk attendant Dennecia was wonderful and was able to get us moved for our last night in Portland. She made the experience enjoyable. She did as much as she could. Just not sure why the hotel couldn’t fix the A/C in the rooms with KNOWN issues.

Reviewed on 8 Jul 2026

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was £1,775, price is now £1,628 per person
£1,628
per person
26 Sept - 30 Sept
found 21 hours ago
Return flight included
Aberdeen (ABZ) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Spacious with plenty of room for my family of four. Excellent kitchen, washer and dryer and stellar location close to Waterfront district.

Reviewed on 5 Jul 2026

Cundys Harbour Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC

Top hotels in Cundys Harbor

Ocean Gate Inn

Ocean Gate Inn

3 out of 5
70 Ocean Gate Rd Southport ME
The price is £217 per night from 29 Jul to 30 Jul
£217
29 Jul - 30 Jul
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"This is an amazing escape from a busy travel area! Great activities for a family."

Reviewed on 8 Jul 2026

Ocean Gate Inn
Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
200 Townsend Avenue Boothbay Harbor ME
Fully refundableReserve now, pay when you stay
The price is £126 per night from 13 Jul to 14 Jul
£126
13 Jul - 14 Jul
includes taxes & fees
8/10 Very good! (1,006 reviews)
"The room was decent. This is definitely an older hotel, but our stay was perfectly fine. The price was was excellent compared to the other hotels a bit closer to the harbor. The pool looked very nice, we just didn't have a chance to use it. The free breakfast was really good."

Reviewed on 7 Jul 2026

Flagship Inn and Suites
Travelers Inn

Travelers Inn

2 out of 5
130 Pleasant St Brunswick ME
Fully refundableReserve now, pay when you stay
The price is £91 per night from 15 Jul to 16 Jul
£91
15 Jul - 16 Jul
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
"We had a bit if delay checking in due to the card reader not working. However, they let us move in and return later to pay. There was a nice table with two chairs as well as deak, frig, and 2 nightstands. Ample parking. The bug surprise was the breakfast. It was a continental, but there were bagels ..."

Reviewed on 8 Jul 2026

Travelers Inn
See all 1,569 properties in Cundys Harbor
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

Frequently asked questions

How much does a Cundys Harbour travel package cost?
From as little as £1,418, you can handcraft your own Cundys Harbour package. Simply combine hotels, flights and car rentals and we'll reward you with discounts.
If I'm not able to travel, can I cancel my Cundys Harbour travel package?
Because we understand life can throw you a few curveballs, the answer is yes. To find out more, check out our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel or change it for free. Your hotel, airline or car rental company may impose a fee if your booking is older than that.
How do I get a cheap travel package to Cundys Harbour?
Browse and lock in everything all in one place with our Cundys Harbour travel packages. You'll discover bargains on flights, hotels, tours and more that'll keep your travel budget happy and your spirit of adventure alive. And, with more than 550 partner airlines and 1,000,000 hotel options globally to pick from, you have countless opportunities to mix and match your own way.
Does Expedia offer Book Now, Pay Later Cundys Harbour holidays?
Your bank balance shouldn't prevent you from escaping on holiday, so Expedia has worked out a solution to help. Now that we've formed a partnership with online lender Klarna, it's easier than ever to book a fabulous getaway without hurting your hip pocket. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your escape. Consider one of these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month sounds best for you, Klarna can help. Paying in easy monthly instalments will make that dream getaway possible.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay for your holiday in multiple transactions.
  • Low deposit holidays: When you spot an unbeatable deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you secure your getaway.

What are the top hotels in Cundys Harbour?
If it's your first visit to Cundys Harbour, lock in a room at Dog - Friendly Home With High - Speed Wifi or Cosy Cottage. Both hotels offer comfortable beds and are top options with many travellers.
How far in advance should I book my Cundys Harbour holiday?
Search Expedia to compare airfares as soon as possible. In most cases, you can purchase a seat up to a year before departure. If you can't find your preferred air carrier, or you're booking late, don't stress. Cheap tickets to Cundys Harbour sometimes emerge a few weeks before departure.
What does an Expedia Cundys Harbour travel package include?
With Expedia, you can select a combination of flights, hotels and car rentals to build your perfect Cundys Harbour travel package. Once you've made your booking, you can add on the fun stuff like tours and activities. Remember, the more you bundle, the more you stand to save!
What should I know before booking a Cundys Harbour travel package?
When you book your flights, hotels and car rentals together, you'll score fantastic discounts. Whether you're organising a wilderness getaway in a cabin or prefer to stay in a luxurious city hotel, Expedia will help make it happen.
Can I choose my airline with a Cundys Harbour Expedia travel package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines worldwide. Our travel packages give you the flexibility to take your pick of available flights, hotels and activities that suit you.

Explore a world of travel with Expedia

* 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.