Title: Bailey Island Vacation Packages & Trips 2026 from CA $1,177 | Expedia.ca

[Bailey Island Travel Guide](https://expedia.ca/Bailey-Island.dx6046825)[Hotels in Bailey Island](https://expedia.ca/Bailey-Island-Hotels.d6046825.Travel-Guide-Hotels)[Vacation Rentals in Bailey Island](https://expedia.ca/Bailey-Island-Vacation-Rentals.d6046825.Travel-Guide-VacationRentals)[Bailey Island Car Rentals](https://expedia.ca/Car-Rentals-In-Bailey-Island.d6046825.Car-Rental-Guide)

![](https://images.trvl-media.com/place/6046825/7787ff8e-ec8a-4628-8f3d-1af96a802dbe.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Bailey Island Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

#### 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](https://www.expedia.ca/Bailey-Island-Bridge-Bailey-Island.d6077256.Vacation-Attraction), [Lands End Gift Shop](https://www.expedia.ca/Lands-End-Gift-Shop-Bailey-Island.d553248621532668102.Vacation-Attraction) and [Ragged Island](https://www.expedia.ca/Ragged-Island-Maine.d553248635976196478.Vacation-Attraction). 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 Westin Portland Harborview](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/67608060_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Westin Portland Harborview

Downtown Portland

CA $1,177

per person

Feb 21 - Feb 28

found 23 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Portland (PWM)

8.8/10 Excellent! (1,001 reviews)

Front end lady very rude. Long hair, didn’t get her name. Young gentleman very nice, solved a misunderstanding with great customer service.

Reviewed on Dec 4, 2025

![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/83fe4590_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Portland Harbor Hotel

Downtown Portland

CA $1,251

per person

Feb 21 - Feb 28

found 23 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Portland (PWM)

9.2/10 Wonderful! (1,668 reviews)

Lovely stay in a beautiful room, appreciated the upgrade. Easy walk to downtown activities.

Reviewed on Dec 12, 2025

![Embassy Suites by Hilton Portland Maine](https://images.trvl-media.com/lodging/1000000/20000/14800/14751/cbc24127_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Embassy Suites by Hilton Portland Maine

CA $1,208

per person

Feb 21 - Feb 28

found 23 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Portland (PWM)

9.4/10 Exceptional! (1,121 reviews)

Room was good, bed snd shower were decent. Property feels a wee bit dated. Staff were nice. Restaurant/bar on site. Airport shuttle! About a mile from jetport. Great overnight spot for early morning flight out.

Reviewed on Dec 8, 2025

![Inn By The Sea](https://images.trvl-media.com/lodging/2000000/1550000/1542800/1542725/d0fca35d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Inn By The Sea

CA $1,575

per person

Jan 16 - Jan 22

found 9 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Portland (PWM)

9.4/10 Exceptional! (288 reviews)

Room was ready early friendly staff and room is better than expected

Reviewed on Nov 16, 2025

![Hampton Inn Portland Downtown - Waterfront](https://images.trvl-media.com/lodging/5000000/4490000/4480300/4480291/1dc67cbc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hampton Inn Portland Downtown - Waterfront

Downtown Portland

CA $1,250

per person

Feb 21 - Feb 28

found 23 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Portland (PWM)

8.8/10 Excellent! (1,002 reviews)

clean room, digital key wonderful, good breakfast selection, staff very accommodating. Pool water very, very cloudy (negative)

Reviewed on Dec 9, 2025

## Ready to book your vacation to Bailey Island?

Choose your dates

## Bailey Island Hotel Deals

![New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach](https://images.trvl-media.com/lodging/28000000/27120000/27118300/27118287/c81a9afc_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

 Bailey Island ME

10/10 Exceptional! (212 reviews)

Wonderful house. Well equipped. Gorgeous view.

Reviewed on Nov 29, 2025

[Get rates](https://expedia.ca/Hotel-Search?startDate=29%2F12%2F2025&endDate=30%2F12%2F2025&selected=27118287&PinnedHotelID=27118287&HadPinnedHotel=true&regionId=6046825)

[](https://expedia.ca/Hotel-Search?startDate=29%2F12%2F2025&endDate=30%2F12%2F2025&selected=27118287&PinnedHotelID=27118287&HadPinnedHotel=true&regionId=6046825)

![Tru by Hilton Portland Airport Area](https://images.trvl-media.com/lodging/19000000/18960000/18952900/18952854/c3cda57d_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Tru by Hilton Portland Airport Area

369 Maine Mall Road South Portland ME

Fully refundableReserve now, pay when you stay

CA $92

CA $100 total

Jan 11 - Jan 12, 2026

includes taxes & fees

8.8/10 Excellent! (1,646 reviews)

The room was nice and the staff were very nice.

Reviewed on Dec 8, 2025

[](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=18952854&PinnedHotelID=18952854&HadPinnedHotel=true&regionId=6046825)

![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/83fe4590_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Portland Harbor Hotel

468 Fore Street Portland ME

Fully refundableReserve now, pay when you stay

CA $152

CA $220 total

Dec 17 - Dec 18

includes taxes & fees

9.2/10 Wonderful! (1,706 reviews)

Everything was great! However it would nivce if there was a microwave at the snack stations on each floor.

Reviewed on Dec 8, 2025

[](https://expedia.ca/Hotel-Search?startDate=17%2F12%2F2025&endDate=18%2F12%2F2025&selected=898621&PinnedHotelID=898621&HadPinnedHotel=true&regionId=6046825)

[See all 1,772 properties in Bailey Island](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=16%2F12%2F2025&endDate=17%2F12%2F2025&regionId=6046825)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

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- [Great Island Vacation Rentals ](https://www.expedia.ca/Great-Island-Vacation-Rentals.d553248635976193455.Travel-Guide-VacationRentals)

- [Things to do in Harpswell ](https://www.expedia.ca/Things-To-Do-In-Harpswell.d553248635077688915.Travel-Guide-Activities)

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

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