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.
Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

3 out of 5
Downtown Portland
Price was CA $1,521, price is now CA $1,243 per person
CA $1,243
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
8.8/10 Excellent! (1,161 reviews)
The building stands out like a sore thumb. Maybe deviate a bit from the Hyatt materials/color template when expanding into similar historical neighborhoods. Missed opportunity for a signature hotel.

Reviewed on Aug. 20, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Price was CA $1,965, price is now CA $1,433 per person
CA $1,433
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (219 reviews)
This property was beyond expectation. As long as you are comfortable using the app, check in was super easy and so was getting into our suite. The kitchen had everything we could have possibly needed, and having a living space was a great lift from a normal hotel room.

Reviewed on Aug. 16, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Price was CA $1,788, price is now CA $1,328 per person
CA $1,328
per person
Sep 27 - Sep 30
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,005 reviews)
We had an amazing stay at Cliffhouse and were pleasantly surprised by how beautiful it is. The only minor issues we encountered were that the pullout couch was quite uncomfortable for our kids, and it was frustrating that children aren’t allowed in the main pool—everyone with kids ends up crowded around a small pool off to the side. Aside from that, everything else was fantastic!

Reviewed on Aug. 9, 2025

Inn By The Sea

Inn By The Sea

4 out of 5
Price was CA $3,004, price is now CA $2,378 per person
CA $2,378
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (275 reviews)
We chose Inn by the Sea because it was advertised as a “pet-friendly” property with beach access for pets, which was a key factor in our decision. Unfortunately, our experience didn’t quite align with those expectations. We arrived on a Sunday around noon and, as expected, our room wasn’t ready (check-in is at 4:00pm). However, unlike many hotels, we were not offered anything while we waited — no welcome drink, light refreshment, or even an early check-in estimate — despite having to wait the full four hours. Once we checked in, we were told our assigned room was not pet-friendly, and we would be charged for any accidents — despite booking under the premise that this was a pet-friendly stay. Additionally, the restaurant only allows pets in the outdoor seating area, and the pool area is not pet-friendly at all. So while the hotel does accommodate pets in some areas, it’s misleading to call it fully pet-friendly when the main guest amenities are off-limits. That said, the property is beautiful and most of the staff were friendly and professional, which we appreciated. But overall, if you’re traveling with a pet and hoping for a truly integrated experience, this may not be the best fit.

Reviewed on Aug. 18, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $1,626, price is now CA $1,303 per person
CA $1,303
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.2/10 Wonderful! (1,542 reviews)
Lovely and knowledgeable staff. Welcoming and romantic stay in a foodie and artsy community.

Reviewed on Aug. 20, 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 $161 per night from Aug 25 to Aug 26
CA $161
CA $175 total
Aug 25 - Aug 26
includes taxes & fees
7.8/10 Good! (1,190 reviews)
"Good hotel for transit"

Reviewed on Aug. 18, 2025

Days Inn by Wyndham Airport/Maine Mall
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $211 per night from Aug 25 to Aug 26
CA $211
CA $233 total
Aug 25 - Aug 26
includes taxes & fees
7.8/10 Good! (1,018 reviews)
"The hotel definitely needs a facelift but it was fine for a brief one night stay. The bed was comfortable. When the elevator got stuck on the 5th floor while we waited in the lobby, the front desk clerk was quick to walk up the 5 flights to address the situation."

Reviewed on Aug. 17, 2025

Clarion Hotel 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 $174 per night from Sep 2 to Sep 3
CA $174
CA $193 total
Sep 2 - Sep 3
includes taxes & fees
7.6/10 Good! (1,052 reviews)
Everyone was great
"Just what i needed"

Reviewed on Aug. 18, 2025

Ramada Plaza by Wyndham Portland
See all 1,801 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.
All Inclusive Vacations
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Frequently asked questions

How much does a Bailey Island vacation package cost?
Offering excellent value package deals from CA $1,243 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.