Cundys Harbor Vacations from $293

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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!

The Latest Cundys Harbor vacation packages

Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $466, price is now $293 per person
$293
per person
Jan 22 - Jan 25
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.2/10 Wonderful! (1,621 reviews)
Clean, courteous, and helpful. Would love to stay another time!

Reviewed on Nov 1, 2025

The Docent's Collection - New Opening

The Docent's Collection - New Opening

2 out of 5
Downtown Portland
Save 100% on your flight
Price was $676, price is now $444 per person
$444
per person
Jan 22 - Jan 25
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
No reviews
Really nice and clean new hotel!

Reviewed on Oct 27, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $2,209, price is now $1,578 per person
$1,578
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,016 reviews)
Absoltely incredible views- the cliffs were the perfect place to catch the sunrise. The restaurant was wonderful and the staff were super friendly and helpful. Extremely comfortable room and the hot tub and indoor pool were fantastic.

Reviewed on Oct 20, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $574, price is now $438 per person
$438
per person
Jan 22 - Jan 25
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (239 reviews)
Cleanliness, staff in lobby were helpful.

Reviewed on Oct 28, 2025

Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront

3 out of 5
Downtown Portland
Price was $480, price is now $374 per person
$374
per person
Jan 22 - Jan 25
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.2/10 Wonderful! (1,016 reviews)
Wonderful room, great staff and great breakfast. Also enjoyed the hot tub.

Reviewed on Oct 28, 2025

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Discover the most popular places to visit in Cundys Harbor

Ash Cove Pottery

Enjoy an outing to Ash Cove Pottery during your stay in Harpswell. Amble around the area's seaside, or seek out its hiking trails.

Ash Cove Pottery

What to do in Cundys Harbor

Historic Bath Maine Neighborhood Walking Tour

Historic Bath Maine Neighborhood Walking Tour

$33
per adult
80% of travellers recommend
Historic Bath Maine Neighborhood Walking Tour
See all activities in Cundys Harbor

Cundys Harbor Hotel Deals

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
$88 nightly
The price is $96 total per night from Nov 6 to Nov 7
$96 total
Nov 6 - Nov 7
Total with taxes and fees
7.6/10 Good! (1,025 reviews)
Nice simple and clean hotel. Staff were helpful and room was spacious. This is an older hotel that has been nicely renovated and very good value for money. No breakfast at the hotel but the cafe beside it does great food for a very good price. Recommend this place if you are looking for a nice hotel ...

Reviewed on Oct 15, 2025

Best Western Freeport Inn
Casco Bay Inn

Casco Bay Inn

2 out of 5
107 US Route 1, Freeport, ME
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $97 total per night from Dec 1 to Dec 2
$97 total
Dec 1 - Dec 2
Total with taxes and fees
8/10 Very Good! (1,049 reviews)
Large rooms and a quiet location. A very basic hotel good for a one-night stay.

Reviewed on Oct 23, 2025

Casco Bay Inn
The Freeport Hotel, an Ascend Collection Hotel

The Freeport Hotel, an Ascend Collection Hotel

2 out of 5
506 Us Route 1, Freeport, ME
Fully refundable
$90 nightly
The price is $98 total per night from Nov 16 to Nov 17
$98 total
Nov 16 - Nov 17
Total with taxes and fees
7.8/10 Good! (1,004 reviews)
Decent enough hotel for a one night stay.

Reviewed on Oct 26, 2025

The Freeport Hotel, an Ascend Collection Hotel
See all 1,426 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.

Find the Best Cundys Harbor Vacation Packages

Cundys Harbor Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)

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Frequently asked questions

How much does a Cundys Harbor vacation package cost?
You'll find cheap prices from $293 on Expedia for your Cundys Harbor getaway. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Cundys Harbor costs.
What are the cheapest months to go to Cundys Harbor?
November, December and January are great times to look for cheap Cundys Harbor vacation packages. Choosing to travel in less busy months means you can typically find better prices on accommodations and flights.
How many days is enough for Cundys Harbor?
The ideal duration for your Cundys Harbor vacation depends on what you'd like to see and do. Usually, a few days to a week will give you time to hit all the major attractions and discover some hidden treasures along the way.
How to find the best Cundys Harbor package deals?
Use Expedia's handy filters to help you find some unbeatable Cundys Harbor package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Cundys Harbor package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Cundys Harbor vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking accommodations and flights separately. Better still, you can tailor your Cundys Harbor getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Cundys Harbor?
Secure amazing discounts by booking your flights early with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Cundys Harbor escape.
Does Expedia offer Book Now, Pay Later Cundys Harbor vacation packages?
If you're like us, you love going away but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Cundys Harbor break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.

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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.