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.
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was CA $1,262, price is now CA $922 per person
CA $922
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
Staff was very helpful, room was clean, and great location! Would definitely stay there again

Reviewed on Jul 14, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $3,159, price is now CA $2,252 per person
CA $2,252
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,775 reviews)
We absolutely loved this beautiful lodging! Insanely perfect location in the heart of the old downtown port area, charming decor, pleasant and helpful staff, clean rooms and common areas, great water pressure in the shower, adorable FREE bicycles with helmets to borrow, and super comfortable beds and bedding. You really can’t ask for anything more! BONUS: our daughter has celiac disease and within the one block radius around the hotel there is a dedicated GF chocolatier, a celiac safe gelato shop(you have to ask which flavors are GF and then they will scoop from the back), and multiple celiac safe dinner options. If you want to drive 15 minutes away(and I highly suggest it!!), there is an INCREDIBLE dedicated gluten free bakery and cafe for breakfast and lunch called Roots Cafe. Everything we had there was SO delicious!!!

Reviewed on Jul 15, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was CA $1,319, price is now CA $966 per person
CA $966
per person
Aug 31 - Sep 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,008 reviews)
Great place to stay! Peaceful area with ample parking. Room was clean & spacious! Beds were comfy. Beautiful area with nice areas to sit outside. Close to many things in the area to go see & do.

Reviewed on Jul 14, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $4,313, price is now CA $3,221 per person
CA $3,221
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (188 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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was CA $2,700, price is now CA $2,051 per person
CA $2,051
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,682 reviews)
Awesome location

Reviewed on Jul 15, 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 $204 per night from Jul 27 to Jul 28
CA $204
CA $226 total
Jul 27 - Jul 28
includes taxes & fees
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 $200 per night from Jul 19 to Jul 20
CA $200
CA $221 total
Jul 19 - Jul 20
includes taxes & fees
8.2/10 Very good! (1,027 reviews)
"It’s reasonable price for a 3 day trip. The room is quiet without hearing any noise from hallway or next door guests. We feel safe at night. Main lobby and breakfast area is nice. Easy to access to the highway. It’s very convenient with all the shopping plaza nearby like Walmart. There are also too ..."

Reviewed on Jul 15, 2026

Fireside Inn & Suites Portland
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
The price is CA $508 per night from Jul 26 to Jul 27
CA $508
CA $616 total
Jul 26 - Jul 27
includes taxes & fees
9.4/10 Exceptional! (1,790 reviews)
"We absolutely loved this beautiful lodging! Insanely perfect location in the heart of the old downtown port area, charming decor, pleasant and helpful staff, clean rooms and common areas, great water pressure in the shower, adorable FREE bicycles with helmets to borrow, and super comfortable beds ..."

Reviewed on Jul 15, 2026

Portland Harbor Hotel
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 $922 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.