Cundys Harbor Vacations from $542

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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.
The McKernan Inn

The McKernan Inn

3 out of 5
Save 100% on your flight
Price was $888, price is now $542 per person
$542
per person
Jan 7 - Jan 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.2/10 Wonderful! (69 reviews)
Picturesque and quiet location! Laundry facilities! Staff was more than accommodating and a lovely ocean view with a delicious breakfast made for a memorable stay!

Reviewed on Oct 21, 2025

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $1,058, price is now $765 per person
$765
per person
Jan 7 - Jan 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.6/10 Exceptional! (155 reviews)
Beautiful historic building. The common areas and our room were stunning! Breakfast in the morning was great. Make sure to go to the widow’s walk in the evening for a view.

Reviewed on Oct 16, 2025

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Save 100% on your flight
Price was $1,107, price is now $837 per person
$837
per person
Dec 24 - Dec 28
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (634 reviews)
Nice room and reception rooms. Comfortable bed. Vintage charm but nice modern bathroom. Lots of thoughtful touches like beach towels, umbrellas and afternoon cookies.

Reviewed on Oct 14, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $893, price is now $681 per person
$681
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.2/10 Wonderful! (1,621 reviews)
Staff was sub par for a 4 star hotel. Bartender and wait staff were more concerned about discussing issues with customers than actually serving people right in front of them. Front desk staff were very curt on the phone.

Reviewed on Oct 23, 2025

The Docent's Collection - New Opening

The Docent's Collection - New Opening

2 out of 5
Downtown Portland
Price was $1,314, price is now $1,009 per person
$1,009
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
No reviews
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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 Oct 31 to Nov 1
$96 total
Oct 31 - Nov 1
Total with taxes and fees
7.6/10 Good! (1,023 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
$109 nightly
The price is $119 total per night from Oct 26 to Oct 27
$119 total
Oct 26 - Oct 27
Total with taxes and fees
8/10 Very Good! (1,041 reviews)
Very nice place to stay at

Reviewed on Oct 18, 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 refundableReserve now, pay when you stay
$90 nightly
The price is $98 total per night from Nov 23 to Nov 24
$98 total
Nov 23 - Nov 24
Total with taxes and fees
7.8/10 Good! (1,028 reviews)
Not much of a breakfast. It was clean and located close to downtown

Reviewed on Oct 18, 2025

The Freeport Hotel, an Ascend Collection Hotel
See all 1,450 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 $542 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.