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.
Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

2.5 out of 5
Downtown Portland
Price was CA $1,935, price is now CA $1,572 per person
CA $1,572
per person
Oct 9 - Oct 12
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (1,004 reviews)
The staff was remarkable, friendly, ready to help with any need.

Reviewed on Aug. 27, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Price was CA $2,414, price is now CA $1,826 per person
CA $1,826
per person
Oct 9 - Oct 12
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (226 reviews)
Very modern and new condition. Digital key worked pretty well and convenient. Lots of good restaurants within walking distance. We enjoyed our stay.

Reviewed on Aug. 25, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $2,304, price is now CA $1,898 per person
CA $1,898
per person
Oct 9 - Oct 12
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,545 reviews)
Great location. You can walk famous restaurants and it’s pretty safe. The room was clean and the staff were very friendly.

Reviewed on Aug. 25, 2025

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Downtown Portland
Price was CA $2,243, price is now CA $1,852 per person
CA $1,852
per person
Oct 9 - Oct 12
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,009 reviews)
Near the waterfront. Great location in Old Port. We had a wonderful 2 night stay

Reviewed on Aug. 26, 2025

Fortland Island Campground

Fortland Island Campground

1 out of 5
Price was CA $2,331, price is now CA $2,001 per person
CA $2,001
per person
Oct 9 - Oct 12
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
10/10 Exceptional! (3 reviews)

Ready to book your vacation to Cundys Harbor?

 

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Cundys Harbor Hotel Deals

Casco Bay Inn

Casco Bay Inn

2 out of 5
107 US Route 1, Freeport, ME
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Sep 1 to Sep 2
CA $154
CA $168 total
Sep 1 - Sep 2
includes taxes & fees
Casco Bay Inn
Ocean Gate Resort

Ocean Gate Resort

3 out of 5
70 Ocean Gate Rd, Southport, ME
Fully refundableReserve now, pay when you stay
The price is CA $189 per night from Sep 1 to Sep 2
CA $189
CA $241 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
"The water view was so peaceful, and the room was dated but clean and comfortable"

Reviewed on Aug. 23, 2025

Ocean Gate Resort
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 $153 per night from Sep 7 to Sep 8
CA $153
CA $166 total
Sep 7 - Sep 8
includes taxes & fees
7.6/10 Good! (1,006 reviews)
"it was quiet and comfortable and easy to access."

Reviewed on Aug. 22, 2025

Best Western Freeport Inn
See all 1,453 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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What to do in Cundys Harbor

Fun for all ages

Sea Kayak to an Island Tour in Casco Bay

CA $123
per adult
100% of travellers recommend
Sea Kayak to an Island Tour in Casco Bay
See all activities in Cundys Harbor

Frequently asked questions

How much does a Cundys Harbour vacation package cost?
You'll find cheap prices from CA $1,572 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.