Cundys Harbor Vacations from $453

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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
Price was $574, price is now $453 per person
$453
per person
Feb 6 - Feb 9
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
The staff were amazing, the room was clean, and the valet parking was hassle free.

Reviewed on Dec 17, 2025

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Save 100% on your flight
Price was $714, price is now $539 per person
$539
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (649 reviews)
Amazing place. My favourite place to visit over the Christmas period. Will be back next year.

Reviewed on Dec 17, 2025

The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $577, price is now $454 per person
$454
per person
Feb 6 - Feb 9
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
9.6/10 Exceptional! (249 reviews)
Loft was clean, staff was nice. Keep in mind when booking there are no laundry facilities in unit or building, no pool, no front desk, no snack/drink counter or restaurant attached, and no shuttle service from airport. You get a furnished loft with basic toiletries, cooking gear, table/drinkware, and dish tv. There is definitely a sense of "things left to be desired" especially for the pricing. I expected itinerary ideas, restaurant suggestions, etc. But none of that was available or offered.

Reviewed on Dec 1, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Price was $831, price is now $664 per person
$664
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
My husband and I had a wonderful time. Breakfast, lunch, and dinner was delicious, drinks were crafted just right. We absolutely loved the outdoor hot tub. Our stay was everything we expected. Thank you.

Reviewed on Dec 8, 2025

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $804, price is now $645 per person
$645
per person
Feb 6 - Feb 9
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
9.6/10 Exceptional! (161 reviews)
The property is beautiful, the staff is kind, and the rooms are spacious and clean. It was great to have a safe place to park the car while having so many things to do within walking distance. Being able to grab a quick breakfast before heading out was great too! We loved our stay here!

Reviewed on Nov 23, 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

Cundys Harbor Hotel Deals

Hilton Garden Inn Freeport Downtown

Hilton Garden Inn Freeport Downtown

3 out of 5
5 Park St Freeport ME
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $106 total per night from Dec 30 to Dec 31
$106 total
Dec 30 - Dec 31
Total with taxes and fees
9/10 Wonderful! (1,000 reviews)
Staff, room, bar and pool were all great! Everything was clean and everyone was friendly and accommodating.

Reviewed on Dec 13, 2025

Hilton Garden Inn Freeport Downtown
Comfort Inn Brunswick

Comfort Inn Brunswick

2.5 out of 5
199 Pleasant St Brunswick ME
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $100 total per night from Dec 28 to Dec 29
$100 total
Dec 28 - Dec 29
Total with taxes and fees
8.8/10 Excellent! (1,004 reviews)
The room was clean and smelled great when we arrived. Very cozy, quiet, comfortable hotel. The staff were very nice. Breakfast was great. Will absolutely be staying again!

Reviewed on Dec 15, 2025

Comfort Inn Brunswick
Holiday Inn Express Hotel & Suites Freeport by IHG

Holiday Inn Express Hotel & Suites Freeport by IHG

2.5 out of 5
450 U.S. Route 1 Freeport ME
Fully refundable
$94 nightly
The price is $102 total per night from Dec 21 to Dec 22
$102 total
Dec 21 - Dec 22
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
Quiet

Reviewed on Dec 17, 2025

Holiday Inn Express Hotel & Suites Freeport by IHG
See all 1,424 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 $453 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.