Cundys Harbor Vacations from $513

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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.
Dormir

Dormir

3 out of 5
Price was $643, price is now $513 per person
$513
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
9/10 Wonderful! (1,004 reviews)
I love this place. This is the 2nd time I've stayed here. It's clean, quiet, well located. The staff is friendly and helpful. I would recommend it to anyone.

Reviewed on Nov 3, 2026

Admiral Peary Inn

Admiral Peary Inn

3 out of 5
Price was $1,674, price is now $1,108 per person
$1,108
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Portland (PWM)
8.8/10 Excellent! (65 reviews)
Very unique and fun history.

Reviewed on Oct 27, 2026

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $778, price is now $624 per person
$624
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
8.6/10 Excellent! (1,007 reviews)

Snowvillage Inn

Snowvillage Inn

4 out of 5
Price was $1,799, price is now $1,469 per person
$1,469
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Portland (PWM)
8.8/10 Excellent! (319 reviews)
A quaint property with tons of hidden gems. Nestled on a mountainside, Snowvillage

Reviewed on Oct 24, 2026

Waldo Emerson Inn

Waldo Emerson Inn

3 out of 5
Price was $922, price is now $759 per person
$759
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
8.8/10 Excellent! (357 reviews)
Our stay at the Waldo Emerson was nothing short of exceptional! From the moment we arrived, Amelia welcomed us with warm hospitality, and every detail of this charming property made us feel right at home. The accommodations were comfortable and full of character, and the property itself is absolutely beautiful. Each morning, we looked forward to a delicious, fresh, and thoughtfully prepared breakfast that was the perfect start to our day. What truly made our experience special were the wonderful sightseeing and dinner recommendations. Amelia and Ron are phenomenal hosts who go above and beyond to ensure their guests have a memorable stay. Their genuine warmth, local knowledge, and attention to detail made our visit to Kennebunkport even more enjoyable. The Waldo Emerson is an outstanding choice for anyone looking for a charming bed and breakfast in Kennebunkport. We thoroughly enjoyed our stay and would gladly return. We highly recommend it to anyone seeking the perfect combination of comfort, charm, exceptional hospitality, and relaxation! **A truly wonderful experience from start to finish!**

Reviewed on Oct 18, 2026

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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
$128 nightly
The price is $140 total per night from Nov 11 to Nov 12
$140 total
Nov 11 - Nov 12
Total with taxes and 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
$88 nightly
The price is $96 total per night from Nov 9 to Nov 10
$96 total
Nov 9 - Nov 10
Total with taxes and 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
$89 nightly
The price is $97 total per night from Nov 5 to Nov 6
$97 total
Nov 5 - Nov 6
Total with taxes and fees
Moonlight Inn
See all 1,522 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

What's included in a Cundys Harbor vacation package?
Cundys Harbor vacation packages typically bundle round-trip flights, a hotel stay, and a rental car. Many accommodations in this beach destination offer convenient access to the coastline, allowing you to easily enjoy the area's natural beauty.

Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
How can I save money on a Cundys Harbor vacation package?
When you bundle, you can save up to 30%*. To save money on a Cundys Harbor package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
Is Cundys Harbor better suited for a beach vacation or a cultural trip?
Cundys Harbor is primarily an outdoor and nature destination, making it an excellent choice for a Cundys Harbor vacation focused on coastal scenery and outdoor activities. The area is known for its beaches, with options like Popham Beach about 12 miles from the center, offering classic Maine shoreline experiences.

While the focus is on nature, there are cultural elements to explore. You can visit the Maine Maritime Museum, about 9 miles away, to delve into the region's seafaring history. Overall, Cundys Harbor works best for travelers seeking a blend of natural beauty and coastal relaxation, with opportunities for historical discovery.
What are the top things to do in Cundys Harbor?
A Cundys Harbor vacation offers a mix of coastal exploration, scenic views, and local history:

Browse and book things to do in Cundys Harbor on Expedia.
Do you need to rent a car in Cundys Harbor, or is public transport enough?
For a Cundys Harbor vacation package, renting a car offers the most flexibility, especially since it's an outdoor and nature destination with attractions spread out. While some accommodations might offer limited local transport, a personal vehicle allows you to fully explore the scenic coastline, various beaches, and charming towns at your own pace.

This is particularly true for Cundys Harbor beach vacation packages, as a car makes it easy to visit different coastal spots and natural areas. For travelers arriving via flights, such as into Portland International Jetport (PWM), a rental car can be picked up directly at the airport, providing seamless travel throughout your Cundys Harbor vacation.
Can I change or cancel my Cundys Harbor vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Cundys Harbor vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Cundys Harbor vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Cundys Harbor vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Cundys Harbor?
To find last-minute vacation packages to Cundys Harbor, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Cundys Harbor vacation packages?
Free cancellation on a Cundys Harbor vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Cundys Harbor vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Cundys Harbor getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Cundys Harbor vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.