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.
Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront

3 out of 5
Downtown Portland
per person
Sep 28 - Sep 30
found 6 hours ago
Roundtrip flight included
Vancouver (YVR) to Portland (PWM)
9.2/10 Wonderful! (1,002 reviews)
Great location, exceptionally welcoming staff.

Reviewed on Aug. 11, 2025

Holiday Inn Express Hotel & Suites Freeport by IHG

Holiday Inn Express Hotel & Suites Freeport by IHG

2.5 out of 5
per person
Oct 28 - Nov 1
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8.6/10 Excellent! (1,004 reviews)
Nice quiet place to stay

Reviewed on Aug. 2, 2025

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Downtown Portland
per person
Sep 28 - Sep 30
found 6 hours ago
Roundtrip flight included
Vancouver (YVR) to Portland (PWM)
9.4/10 Exceptional! (1,004 reviews)
This hotel is centrally located with many dining options in the Old Port area. It also has a nice rooftop bar with nice views. The room was spacious and very pleasant, everything was clean and well taken care of. Great place to stay in Portland!

Reviewed on Aug. 10, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
Sep 28 - Sep 30
found 6 hours ago
Roundtrip flight included
Vancouver (YVR) to Portland (PWM)
9.2/10 Wonderful! (1,542 reviews)
Great option in Old Port. Very convenient to dining, shopping and boat tours. You can walk to everything. Courtyard was lovely in the evening for cocktails around the firepit. Would definitely recommend!

Reviewed on Aug. 7, 2025

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
per person
Sep 28 - Sep 30
found 6 hours ago
Roundtrip flight included
Vancouver (YVR) to Portland (PWM)
9.4/10 Exceptional! (1,368 reviews)
This hotel is in the heart of everything! Fast and easy check in. Clean, hot water, the sink was a little clogged but that doesn’t stop anything. Would stay here again.

Reviewed on Aug. 8, 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 $160 per night from Aug 24 to Aug 25
CA $160
CA $174 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,142 reviews)
"Bed was comfort. Good choice for delivery"

Reviewed on Aug. 9, 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 $134 per night from Aug 24 to Aug 25
CA $134
CA $146 total
Aug 24 - Aug 25
includes taxes & fees
7.4/10 Good! (132 reviews)
"Everything from Germaine Inn South Portland is pretty good rooms, facilities, pool etc.. I only whish they provide breakfast until 10AM instead of 9AM."

Reviewed on Aug. 11, 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 $178 per night from Sep 1 to Sep 2
CA $178
CA $197 total
Sep 1 - Sep 2
includes taxes & fees
7.6/10 Good! (1,039 reviews)
"."

Reviewed on Aug. 9, 2025

Ramada Plaza by Wyndham Portland
See all 1,819 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 $662 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.