Cundys Harbor Vacations from $728

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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.
River View Resort

River View Resort

2.5 out of 5
Save 100% on your flight
per person
Oct 11 - Oct 18
found 3 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
8.8/10 Excellent! (291 reviews)
It was a basic suite-like motel. Could use an upgrade. Very 70s

Reviewed on Mar 30, 2025

The McKernan Inn

The McKernan Inn

3 out of 5
Save 100% on your flight
per person
Sep 22 - Sep 26
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.2/10 Wonderful! (31 reviews)
Away from the busy areas but not far ton

Reviewed on Jul 29, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,008 reviews)
Beautiful property with great service and dining options. Rooms were spacious with nautical decor. Pool was beautiful but get there early if you want a lounge with umbrella!

Reviewed on Jul 30, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
per person
Sep 5 - Sep 8
found 7 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (211 reviews)
Fantastic place to stay when visiting Portland. The location can't be beat -- within a couple of blocks to the ferry terminal and Old Town shops and restaurants. The building is next to a police station and my family and I felt very safe. The unit was immaculate, modern, and fully equipped. Onsite parking was a huge bonus, as was the friendly and helpful staff. I would, without hesitation, stay at The Docent's Collection again.

Reviewed on Jul 31, 2025

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.8/10 Exceptional! (113 reviews)
The Blind Tiger was a gem. It was convenient and private enough to enjoy with staff available 24/7 with and questions. The room, lobby and all areas were immaculate and brilliantly arranged. I would definitely go again!

Reviewed on Jul 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

Casco Bay Inn

Casco Bay Inn

2 out of 5
107 US Route 1, Freeport, ME
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $143 total per night from Aug 3 to Aug 4
$143 total
Aug 3 - Aug 4
Total includes taxes and fees
8.2/10 Very Good! (1,026 reviews)
"Lots of construction, 100 degrees outside and the lobby wasnt air conditioned. The hotel elevator was dirty and operation questionable. Don't even ask about yhr continental breakfast."

Reviewed on Jul 27, 2025

Casco Bay Inn
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
$124 nightly
The price is $135 total per night from Aug 31 to Sep 1
$135 total
Aug 31 - Sep 1
Total includes taxes and fees
7.8/10 Good! (1,014 reviews)
"Nice clean room. We had a beautiful view of the tidal river. No balcony, but a door you could open for fresh air and view. Would have rated 5 ⭐ but the hair dryer didn't work and the tub/shower faucet leaks. Over all a good room for the money."

Reviewed on Jul 29, 2025

Best Western Freeport Inn
Ocean Gate Resort

Ocean Gate Resort

3 out of 5
70 Ocean Gate Rd, Southport, ME
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $193 total per night from Sep 1 to Sep 2
$193 total
Sep 1 - Sep 2
Total includes taxes and fees
8.4/10 Very Good! (1,013 reviews)
"Excellent spot. Highly recommend with a lot of activities for families. All activities and breakfast included in price. We went sea kayaking, swimming and did mini put."

Reviewed on Jul 27, 2025

Ocean Gate Resort
See all 1,469 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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Frequently asked questions

How much does a Cundys Harbor vacation package cost?
You'll find cheap prices from $728 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.