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 $1,289, price is now CA $1,099 per person
CA $1,099
per person
Aug 20 - Aug 24
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
Loved kayaking in the bay

Reviewed on Jun 30, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was CA $1,699, price is now CA $1,167 per person
CA $1,167
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,017 reviews)
Every thing was nice and excellent

Reviewed on Jun 30, 2026

Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
Price was CA $2,087, price is now CA $1,565 per person
CA $1,565
per person
Jul 30 - Aug 2
found 5 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Portland (PWM)
8.8/10 Excellent! (196 reviews)
We had a really wonderful visit at the Inn at Diamond Cove. It was a special adventure and the staff tried to work with us to help us enjoy our visit after arriving very late at night for a one night /one day stay. We knew nothing about the inn or the island's history so it was a leap of faith and well worth it.

Reviewed on Jun 29, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $2,567, price is now CA $1,990 per person
CA $1,990
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Portland (PWM)
9.6/10 Exceptional! (185 reviews)
We were only there for 1 night, but the innkeeper made a great suggestion for dinner. Overall a great place and would stay again.

Reviewed on Jun 26, 2026

The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

3.5 out of 5
Downtown Portland
Price was CA $2,545, price is now CA $2,213 per person
CA $2,213
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Portland (PWM)
9.8/10 Exceptional! (34 reviews)
Fantastic place to stay!

Reviewed on Jun 25, 2026

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Bailey Island Hotel Deals

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
340 Park Ave Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from Jul 1 to Jul 2
CA $190
CA $211 total
Jul 1 - Jul 2
includes taxes & fees
8.6/10 Excellent! (2,195 reviews)
"The bed sheets were dirty, hair and stains. I have a strong feeling that they were not changed. Everything else was fine."

Reviewed on Jun 30, 2026

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
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 $401 per night from Jul 5 to Jul 6
CA $401
CA $498 total
Jul 5 - Jul 6
includes taxes & fees
9.4/10 Exceptional! (1,775 reviews)
"Clean room but the room wasn't well cleaned during the stay. They picked up towels but I noticed trash on the floor. The 35 facility fee is a joke. Not much to use for 35. If you have breakfast or drinks then the fee is waved. Air conditioning wasn't working. Never got below 74 degrees F in room ..."

Reviewed on Jun 29, 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 $355 per night from Jul 5 to Jul 6
CA $355
CA $432 total
Jul 5 - Jul 6
includes taxes & fees
9.4/10 Exceptional! (1,252 reviews)
"Great location, beautiful, modern rooms with big bathrooms, comfortable beds, spacious areas for storing luggage, etc. and terrific electric black out shades. Very quiet and peaceful. Beautiful garden in the back and easy access to parking garage and Old Port activities. Highly recommend."

Reviewed on Jun 29, 2026

Cambria Hotel Portland Downtown-Old Port
See all 1,855 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

9.2/5 (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 $1,099 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.