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.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

Moody
CA $786
per person
Sep 20 - Sep 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9/10 Wonderful! (1,020 reviews)
Un séjour parfait ! Très bon service. Excellent déjeuner. Très propre. Un site extérieur relaxant et très beau près de la nature. Je vais y retourner assurément !!!!

Reviewed on Aug 8, 2026

The Meadowmere Resort

The Meadowmere Resort

CA $987
per person
Sep 20 - Sep 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
We had never been to the Meadowmere. It struck me as a mid-century resort. I felt the room we had, 2nd floor of The Pines building, had been tastefully updated. I only interacted with the front desk and they were nice, in spite of an irate woman there when I was who refused to be happy about anything. I was worried that there might be noise from other guests, but the AC was so loud I couldn’t hear anything. That was a good thing for me. Slept great. We were only there one night. Very walkable to town. We had reservations at The Front Porch.

Reviewed on Aug 8, 2026

Evalina Hotel

Evalina Hotel

Downtown Portland
CA $2,270
per person
Oct 14 - Oct 17
found 2 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
10/10 Exceptional! (7 reviews)
It was our first time visiting Portland, and the Evalina exceeded our expectations. The location is perfect, right on Commercial Street, with plenty of restaurants and shops nearby. The ferry and cruise ports are also just a 5–10 minute walk away, making it easy to visit the different islands. The suite was comfortable and thoughtfully equipped with everything we could need, including an umbrella for rainy days, coffee and a French press, tea, a washer and dryer, and so much more. Communication was excellent throughout our stay as well. We truly enjoyed our visit, and the next time we’re in Portland, the Evalina will be our first choice!

Reviewed on Aug 8, 2026

Portland Harbor Hotel

Portland Harbor Hotel

Downtown Portland
CA $1,328
per person
Sep 20 - Sep 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,792 reviews)
We had a shower that leaked all the way out to the foyer. We called and reported it. They sent a repair person. They caulked around the edge which helped but didn’t fix the whole problem. It still leaked, just not as bad. No one followed up to see if it was fixed. They have a pantry on each floor with fruit infused water snacks, fresh fruit, cookies, canned sparkling water and ice for free. But it was mostly depleted most of the time we were there. There was a sign advertising live music at the front of the hotel. But when we asked where it was, the hotel attendant said they were not having live music after all. No one went to take the sign down. It was still there the next day. We checked out. Hope the musician showed up that night.

Reviewed on Aug 7, 2026

River View Resort

River View Resort

CA $1,302
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9/10 Wonderful! (331 reviews)
The room was clean (but a bit dated), and comfortable. Staff was welcoming and very friendly. It was perfect to stay w/ my mother and teen-aged son. It was nice to have a full kitchen, and conveniently supplied with the essentials. We would stay there again!

Reviewed on Aug 4, 2026

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Cundys Harbor Hotel Deals

Flagship Inn and Suites

Flagship Inn and Suites

200 Townsend Avenue Boothbay Harbor ME
CA $145
CA $212 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very good! (1,014 reviews)
"very pleasant, quiet stay"

Reviewed on Aug 8, 2026

Flagship Inn and Suites
The Freeport Hotel, an Ascend Collection Hotel

The Freeport Hotel, an Ascend Collection Hotel

506 Us Route 1 Freeport ME
Fully refundable
CA $137
CA $149 total
Aug 30 - Aug 31
includes taxes & fees
7.8/10 Good! (1,018 reviews)
"Dirty property, did not have hot water. Dirty bathrooms, dirty rugs, the whole building and room had an odor. Beds were uncomfortable, paint chipping on walls, dirty hand prints and feet on walls. Would not recommend."

Reviewed on Aug 8, 2026

The Freeport Hotel, an Ascend Collection Hotel
Holiday Inn Express Hotel & Suites Freeport by IHG

Holiday Inn Express Hotel & Suites Freeport by IHG

450 U.S. Route 1 Freeport ME
Fully refundable
CA $195
CA $213 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"Room was clean, great staff, great breakfast and great parking"

Reviewed on Aug 5, 2026

Holiday Inn Express Hotel & Suites Freeport by IHG
See all 1,605 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.

Frequently asked questions

How much does a Cundys Harbour vacation package cost?
You'll find cheap prices from CA $786 on Expedia for your Cundys Harbour break. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Cundys Harbour costs.
What are the cheapest months to go to Cundys Harbour?
You're likely to find lower rates and greater availability in January, February and March. Check out our cheap Cundys Harbour vacation packages and you could get some excellent off-season deals.
How many days is enough for Cundys Harbour?
The ideal length of your Cundys Harbour vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you enough time to visit all the major sights and discover some hidden treasures along the way.
How to find the best Cundys Harbour package deals?
Bagging a cheap Cundys Harbour package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, add a few filters and see what's available. You can customize your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Cundys Harbour package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Cundys Harbour vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component individually. And you'll still have the flexibility to create a tailored Cundys Harbour vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Cundys Harbour?
If you're considering a spontaneous Cundys Harbour adventure, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score awesome deals on your flights and hotels by booking ahead.
How to plan a trip to Cundys Harbour?
  1. Pick your dates: The things you'd like to do in Cundys Harbour and your favourite season can help you decide when to travel.
  2. Set a budget: Consider expenses such as flights, meals and transportation when working out how much to put aside for your trip to Cundys Harbour. Then, select a property that works with your budget, whether that's a wallet-friendly stay or a high-end retreat.
  3. Decide your trip length: Consider how long you'd like to spend discovering Cundys Harbour. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Cundys Harbour vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.