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.
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Nasons Corner
Price was CA $966, price is now CA $800 per person
CA $800
per person
Oct 14 - Oct 18
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
7.8/10 Good! (1,009 reviews)
Everything in room didn’t work

Reviewed on Aug 1, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was CA $1,802, price is now CA $1,245 per person
CA $1,245
per person
Sep 3 - Sep 7
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9/10 Wonderful! (1,008 reviews)
.

Reviewed on Aug 2, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $2,981, price is now CA $2,266 per person
CA $2,266
per person
Sep 11 - Sep 13
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (188 reviews)
This hotel is amazing. The rooms, beds, and all the details are so incredible. I wish I could have stayed longer. Check in was a breeze as well. You can tell they take a lot of care and thought into the property. I will definitely be back

Reviewed on Jul 25, 2026

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was CA $2,227, price is now CA $1,851 per person
CA $1,851
per person
Oct 14 - Oct 18
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (362 reviews)
Would stay again for sure.

Reviewed on Jul 31, 2026

Dormir

Dormir

3 out of 5
Price was CA $1,028, price is now CA $883 per person
CA $883
per person
Oct 14 - Oct 18
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
8.8/10 Excellent! (1,002 reviews)

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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 $184 per night from Sep 1 to Sep 2
CA $184
CA $203 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very good! (1,593 reviews)
"The staff is great. The property is dated. Great location with proximity to the airport."

Reviewed on Aug 1, 2026

Clarion Hotel Portland Airport ME
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Sep 1 to Sep 2
CA $154
CA $170 total
Sep 1 - Sep 2
includes taxes & fees
Fireside Inn & Suites Portland
Clarion Pointe South Portland

Clarion Pointe South Portland

2 out of 5
675 Main Street I-95 South Portland ME
Fully refundable
The price is CA $130 per night from Sep 1 to Sep 2
CA $130
CA $142 total
Sep 1 - Sep 2
includes taxes & fees
7.4/10 Good! (621 reviews)
"They were overbooked and rather than admit it they made us wait at least 30 minutes before they offered to find us a comparable room in another hotel"

Reviewed on Aug 1, 2026

Clarion Pointe South Portland
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 $800 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.

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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.