Cundys Harbor Vacation Packages
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Your Cundys Harbor Vacation
With all your travel needs organized before you go, our Cundys Harbor vacation packages mean you can focus more on having a good time! One neighborhood to consider staying in this interesting city is Harpswell, which is great for nature and culture. Make your trip to Cundys Harbor 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 Harbor vacation plans into action!
Top Cundys Harbor Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Inn at Diamond Cove
Price was CA $1,647, price is now CA $1,358 per person
CA $1,358
per person
Aug 3 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
8.8/10 Excellent! (196 reviews)
it was very unique having to take a ferry over, shuttle by golf cart and bikes. late in season only 1 restaurant available. looking for peace and quiet- this it the place. lots to walk around and look at with the old fort there.
Reviewed on Sep 25, 2025
The Meadowmere Resort
Price was CA $2,082, price is now CA $1,591 per person
CA $1,591
per person
Aug 31 - Sep 4
found 24 hours ago
Roundtrip flight included
Montreal (YMQ) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
Price was good for the amenities offered and location. Our room was just recently renovated.
Reviewed on Jun 22, 2026
Ogunquit River Inn & Suites
Moody
Price was CA $1,852, price is now CA $1,421 per person
CA $1,421
per person
Aug 31 - Sep 4
found 24 hours ago
Roundtrip flight included
Montreal (YMQ) to Portland (PWM)
9/10 Wonderful! (1,011 reviews)
The staff was excellent and the room immaculate. Our room had no balcony, which was disappointing. It would have been nice to have a small table and chairs in the room.
Reviewed on Jun 27, 2026
Blind Tiger Portland - Danforth Street.
West End
Price was CA $2,557, price is now CA $2,029 per person
CA $2,029
per person
Aug 24 - Aug 28
found 16 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Portland (PWM)
9.6/10 Exceptional! (185 reviews)
We were only there for 1 night, but the innkeeper made a great suggestion for dinner. Overall a great place and would stay again.
Reviewed on Jun 26, 2026
Portland Harbor Hotel
Downtown Portland
Price was CA $2,123, price is now CA $1,706 per person
CA $1,706
per person
Aug 24 - Aug 28
found 16 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Portland (PWM)
9.4/10 Exceptional! (1,786 reviews)
I was told I would get a text when my room was ready, I never did and while sitting in lobby hours later watched multiple guests get their rooms.
I was told as an Expedia VIP, there would be a bottle of wine waiting for me in my room. There was none.
The bed made a loud creaking noise every time I moved. Outlets next to the bed were very loose.
While the location was great; not worth the money
Reviewed on Jun 26, 2026
Cundys Harbor Hotel Deals
Flagship Inn and Suites
200 Townsend Avenue Boothbay Harbor ME
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Jun 29 to Jun 30
CA $186
CA $259 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very good! (1,001 reviews)
"Good location nice breakfast but noisy air conditioner"
Reviewed on Jun 27, 2026
Ocean Gate Inn
70 Ocean Gate Rd Southport ME
The price is CA $360 per night from Jul 1 to Jul 2
CA $360
CA $413 total
Jul 1 - Jul 2
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"The property has been sold as of Jan 2026 and according to office staff, renovations are underway. My room was in good condition with the exception of the privacy blinds which were dusty and inoperable. I was otherwise satisfied with my room, but would have liked to have had a microwave. Staff was ..."
Reviewed on Jun 25, 2026
Best Western Freeport Inn
31 US Route 1 Freeport ME
Fully refundableReserve now, pay when you stay
The price is CA $158 per night from Jul 5 to Jul 6
CA $158
CA $172 total
Jul 5 - Jul 6
includes taxes & fees
7.8/10 Good! (1,002 reviews)
"Clean, quiet (thick windows) motel style hotel. No elevators, Great location."
Reviewed on Jun 25, 2026
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.
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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.
