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.
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (598 reviews)
The breakfast each more was varied and delicious. There are bikes on the property which are great to ride around town

Reviewed on Jul. 29, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,008 reviews)
The Cliff House is a one of a kind! Always a fantastic visit!

Reviewed on Aug. 1, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,542 reviews)
We were pleased with the neighborhood and our actual room. The staff member who checked us in seemed intoxicated and smelled strongly of alcohol. We were told we had a credit to use in the hotel but were charged and never received the credit. The room was very clean and the bed was comfortable. We enjoyed the historic neighborhood.

Reviewed on Aug. 4, 2025

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Downtown Portland
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,009 reviews)
Great location and nice rooms.

Reviewed on Aug. 4, 2025

Inn By The Sea

Inn By The Sea

4 out of 5
per person
Sep 15 - Sep 20
found 20 hours ago
Roundtrip flight included
Edmonton (YEG) to Portland (PWM)
9.6/10 Exceptional! (274 reviews)
It was one of the best getaways we have ever been on. Thank you for your hospitality.

Reviewed on Jun. 13, 2025

Ready to book your vacation to Bailey Island?

 

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Bailey Island Hotel Deals

Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Aug 24 to Aug 25
CA $151
CA $165 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,110 reviews)
"I enjoyed my stay and thought was excellent value for the money. For old property it has been kept up well. I enjoyed they had pool and strong AC in the rooms."

Reviewed on Aug. 3, 2025

Days Inn by Wyndham Airport/Maine Mall
Germaine Inn South Portland

Germaine Inn South Portland

2 out of 5
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
The price is CA $148 per night from Aug 11 to Aug 12
CA $148
CA $161 total
Aug 11 - Aug 12
includes taxes & fees
7.4/10 Good! (111 reviews)
"Great place to stay"

Reviewed on Aug. 1, 2025

Germaine Inn South Portland
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $182 per night from Sep 1 to Sep 2
CA $182
CA $201 total
Sep 1 - Sep 2
includes taxes & fees
7.6/10 Good! (1,044 reviews)
"Great option to explore Portland."

Reviewed on Aug. 3, 2025

Ramada Plaza by Wyndham Portland
See all 1,827 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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Frequently asked questions

How much does a Bailey Island vacation package cost?
Offering excellent value package deals from CA $1,326 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.

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