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.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $1,298, price is now CA $1,170 per person
CA $1,170
per person
Jan 3 - Jan 7
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.2/10 Wonderful! (1,851 reviews)
1/3 of the final bill was parking fees, destination amenity fees and taxes! They even taxed the amenity fees. Hidden costs for booking should be listed! Unbelievable

Reviewed on Nov 9, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $3,860, price is now CA $3,084 per person
CA $3,084
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Portland (PWM)
9.6/10 Exceptional! (199 reviews)

Inn By The Sea

Inn By The Sea

4 out of 5
Price was CA $2,420, price is now CA $2,073 per person
CA $2,073
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Portland (PWM)
9.6/10 Exceptional! (342 reviews)

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 CA $2,497, price is now CA $2,165 per person
CA $2,165
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Portland (PWM)
9.6/10 Exceptional! (419 reviews)
Pros: Room was nice and spacious. Kitchen had everything we needed. Location was awesome - very close to all the things we wanted to do. Excellent proximity to some of the best restaurants, including LB Kitchen, Fore Street, Central Provisions. Con’s: Couches could have benefited from some throw pillows - kinda weird without any. Bed wasn’t that comfortable - you sink in way too much. Parking was ok - just some weird communication before our arrival about where to park. Text messages from the hotel leading up to our check in said they had a lot behind the building which we parked in - only to be told during check in that the lot was only for people that booked it (fair) but their messages made it seem like that was available. Then they questioned how we even knew about the lot - which was odd considering we only knew about it because they texted us parking info.

Reviewed on Nov 8, 2026

Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Price was CA $3,483, price is now CA $3,081 per person
CA $3,081
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Portland (PWM)
10/10 Exceptional! (15 reviews)

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Cundys Harbor Hotel Deals

The Brunswick Hotel

The Brunswick Hotel

3 out of 5
4 Noble St Brunswick ME
Fully refundableReserve now, pay when you stay
The price is CA $170 per night from Nov 16 to Nov 17
CA $170
CA $185 total
Nov 16 - Nov 17
includes taxes & fees
The Brunswick Hotel
Best Western Freeport Inn

Best Western Freeport Inn

3 out of 5
31 US Route 1 Freeport ME
Fully refundableReserve now, pay when you stay
The price is CA $124 per night from Nov 15 to Nov 16
CA $124
CA $136 total
Nov 15 - Nov 16
includes taxes & fees
Best Western Freeport Inn
Moonlight Inn

Moonlight Inn

2 out of 5
215 Pleasant St Brunswick ME
Fully refundableReserve now, pay when you stay
The price is CA $126 per night from Nov 10 to Nov 11
CA $126
CA $137 total
Nov 10 - Nov 11
includes taxes & fees
Moonlight Inn
See all 1,520 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 $1,170 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.