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 Docent's Collection at 121 Middle Street
Downtown Portland
CA $1,454
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (382 reviews)
Immaculate furnishings, hardware, linens, etc. More a rental apt or upscale AirBNB than an inn. Fine if that is what you were expecting. I was expecting more atmosphere (sterile) and service (minimal}.
Indifferent rating for service reflects a combination of staff belaboring obvious points on check in while being unresponsive on follow-up. Example: wanted to leave my bag there after an early checkout so I could spend a few hours around town prior to moving on. That proved too difficult…might as well have been dealing with robots.
Reviewed on Sep 16, 2026
Ready to book your vacation to Bailey Island?
Bailey Island Hotel Deals
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
CA $131
CA $143 total
Sep 17 - Sep 18
includes taxes & fees
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Fully refundable
CA $199
CA $217 total
Sep 27 - Sep 28
includes taxes & fees
8.4/10 Very good! (2,994 reviews)
"Pillows were a little too tall. Shower door could use some adjustment. Room was clean!"
Reviewed on Sep 16, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
CA $165
CA $182 total
Sep 28 - Sep 29
includes taxes & fees
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.
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.
Land's End Gift Shop
10.0/10 (1 review)
Enjoy an outing to Land's End Gift Shop during your stay in Bailey Island. While you're in the area, find time to visit its shops.
Cobwork Bridge
10.0/10 (1 review)
You can find out about the history of Bailey Island when you stop by Cobwork Bridge. Stroll along the seaside or seek out the hiking trails.
beach near Bailey Island
Why not spend a lazy afternoon at beach near Bailey Island during your trip to Bailey Island? Make time to visit the shops and monuments while you're in the area.
beach near Channel View Lane
Why not spend a lazy afternoon at beach near Channel View Lane during your trip to Bailey Island? Make time to visit the shops and monuments while you're in the area.
beach near Mackerel Cove Lot
Why not spend a lazy afternoon at beach near Mackerel Cove Lot during your trip to Bailey Island? Make time to visit the shops and monuments while you're in the area.
beach near Water Cove
Why not spend a lazy afternoon at beach near Water Cove during your trip to Bailey Island? Make time to visit the shops and monuments while you're in the area.
beach near Cragmoor Lane
Why not spend a lazy afternoon at beach near Cragmoor Lane during your trip to Bailey Island? Make time to visit the shops and monuments while you're in the area.
Frequently asked questions
How much does a Bailey Island vacation package cost?
Offering excellent value package deals from CA $1,454 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?
- 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.
- 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.
- 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.
- 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.
