Bailey Island Vacation Packages

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Your Bailey Island Vacation

With one of our vacation packages to Bailey Island, you'll have endless opportunities for relaxation and adventure. There's lots to experience, including its coastal scenery and spectacular views. If sightseeing is on the cards during your trip to Bailey Island, check out popular attractions like Bailey Island Bridge, Lands End Gift Shop and Ragged Island. A few quick clicks is all it takes to build a customized Bailey Island vacation on Expedia.

Top Bailey Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Ocean Gate Inn

Ocean Gate Inn

3 out of 5
Price was CA $1,264, price is now CA $1,077 per person
CA $1,077
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
8.6/10 Excellent! (1,004 reviews)
It was an amazing experience, breakfast was spot on, hotel room is clean, the ocean view was perfect. Being in the woods gives it that real get away, relaxed feeling. We went out on the canoe that they have for free and spent all morning seeing wildlife and sightseeing. We will definitely be coming back.

Reviewed on Jul 12, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $2,206, price is now CA $1,635 per person
CA $1,635
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,775 reviews)
Our stay was great - the location of this hotel is perfect, the staff was friendly and our room was really nice. Every morning, there was a fully stocked pantry with snacks and drinks for guests on each floor. We had a great stay and would recommend this place highly!

Reviewed on Jul 12, 2026

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was CA $2,448, price is now CA $1,863 per person
CA $1,863
per person
Aug 21 - Aug 24
found 8 hours ago
Roundtrip non-stop flight included
Québec (YQB) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
Excellent location and a close walk to town. Gorgeous pool and the room was very clean. I would highly recommend it.

Reviewed on Jul 12, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was CA $2,052, price is now CA $1,592 per person
CA $1,592
per person
Aug 21 - Aug 24
found 8 hours ago
Roundtrip non-stop flight included
Québec (YQB) to Portland (PWM)
9/10 Wonderful! (1,008 reviews)
Clean room and very attentive staff! P

Reviewed on Jul 12, 2026

Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Price was CA $3,084, price is now CA $2,662 per person
CA $2,662
per person
Aug 21 - Aug 24
found 8 hours ago
Roundtrip non-stop flight included
Québec (YQB) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
A beautiful place to spend a special occasion.

Reviewed on Jul 12, 2026

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Bailey Island Hotel Deals

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundable
The price is CA $205 per night from Jul 26 to Jul 27
CA $205
CA $227 total
Jul 26 - Jul 27
includes taxes & fees
8.2/10 Very good! (1,552 reviews)
"They could not accept early check in but we're able to allow use of the pool while waiting for my room which was nice. Overall I will stay here again"

Reviewed on Jul 12, 2026

Clarion Hotel Portland Airport ME
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $559 per night from Jul 19 to Jul 20
CA $559
CA $673 total
Jul 19 - Jul 20
includes taxes & fees
9.4/10 Exceptional! (1,783 reviews)
"Our stay was great - the location of this hotel is perfect, the staff was friendly and our room was really nice. Every morning, there was a fully stocked pantry with snacks and drinks for guests on each floor. We had a great stay and would recommend this place highly!"

Reviewed on Jul 12, 2026

Portland Harbor Hotel
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundable
The price is CA $478 per night from Jul 26 to Jul 27
CA $478
CA $568 total
Jul 26 - Jul 27
includes taxes & fees
9.4/10 Exceptional! (1,264 reviews)
"The room was perfect and spacious; the only downside was the view."

Reviewed on Jul 12, 2026

Cambria Hotel Portland Downtown-Old Port
See all 1,964 properties in Bailey Island
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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Stay near popular Bailey Island attractions

Bailey Island Bridge

9.2/10 (10 reviews)
Find out about the history of Bailey Island when you spend time at Bailey Island Bridge. Stroll along the seaside or seek out the hiking trails.
See properties

Frequently asked questions

How much does a Bailey Island vacation package cost?
Offering excellent value package deals from CA $1,077 on Expedia, you'll be surprised at how little a vacation to Bailey Island costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Bailey Island?
The off-season is the best time to head to Bailey Island if you're trying to keep costs down. Another tip for scoring cheap Bailey Island vacation packages? Avoid visiting during public holidays and any major events.
How many days is enough for Bailey Island?
You can easily visit all the leading sights in Bailey Island in a few days, including the must-see Land's End Gift Shop. If you're after an extended Bailey Island vacation, check out what sort of activities and day trips are available nearby.
Is it worth booking a vacation package to Bailey Island?
Known for its walking trails and home to popular attractions like Cobwork Bridge, a Bailey Island vacation is bound to impress. Another top sight to check out? Don't miss Bailey Island Bridge.
How to find the best Bailey Island package deals?
Bagging a cheap Bailey Island package deal is a breeze with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can fine-tune your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to view the most affordable Bailey Island package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Bailey Island vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and hotels individually. Better still, you can customize your Bailey Island escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Bailey Island?
If you have your Bailey Island travel dates locked in, book early to bag some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for travelling on a whim.
How to plan a trip to Bailey Island?

  1. Choose when to travel: Check your schedule and get your bags packed. Your preferred time of year and the available activities will also help you decide when to escape to Bailey Island.
  2. Figure out your budget: Ensure you have enough money to pay for everything from food and transportation to activities and flights. Your accommodations will likely be the biggest expense during your trip to Bailey Island.
  3. Decide how long to go for: Now that you're more familiar with Bailey Island, you can figure out the right length of your break. Pull together a draft plan and allocate enough time to cover everything you want to see.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to find a Bailey Island vacation package that brings all your bookings together.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.