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

3 out of 5
Moody
Price was CA $1,657, price is now CA $1,284 per person
CA $1,284
per person
Sep 16 - Sep 20
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,008 reviews)

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $3,173, price is now CA $2,272 per person
CA $2,272
per person
Aug 16 - Aug 22
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,775 reviews)

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was CA $1,915, price is now CA $1,481 per person
CA $1,481
per person
Sep 16 - Sep 20
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
Staff was very helpful, room was clean, and great location! Would definitely stay there again

Reviewed on Jul 14, 2026

Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Price was CA $3,429, price is now CA $2,681 per person
CA $2,681
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) 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 Jun 28, 2026

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was CA $2,731, price is now CA $2,203 per person
CA $2,203
per person
Aug 16 - Aug 22
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,682 reviews)

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Cundys Harbor Hotel Deals

Ocean Gate Inn

Ocean Gate Inn

3 out of 5
70 Ocean Gate Rd Southport ME
The price is CA $446 per night from Jul 23 to Jul 24
CA $446
CA $510 total
Jul 23 - Jul 24
includes taxes & fees
8.6/10 Excellent! (1,018 reviews)
"The place was amazing , relaxing and very well cared for ! We loved it and will return soon !"

Reviewed on Jul 15, 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 CA $167 per night from Jul 26 to Jul 27
CA $167
CA $237 total
Jul 26 - Jul 27
includes taxes & fees
8/10 Very good! (1,013 reviews)
"No staff at the property after 9 pm. After hours number was just an answering machine."

Reviewed on Jul 14, 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 CA $157 per night from Jul 19 to Jul 20
CA $157
CA $171 total
Jul 19 - Jul 20
includes taxes & fees
9/10 Wonderful! (1,020 reviews)
"Comfortable, impeccably clean, great value."

Reviewed on Jul 16, 2026

Travelers Inn
See all 1,608 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.
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Frequently asked questions

How much does a Cundys Harbour vacation package cost?
You'll find cheap prices from CA $1,284 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.

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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.