Title: Bailey Island Vacation Packages & Trips 2026 from CA $982 | 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
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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
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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](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.

![84 Main ](https://images.trvl-media.com/lodging/8000000/7810000/7805200/7805164/f78a93a3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### 84 Main 

CA $982

per person

Apr 19 - Apr 25

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Portland (PWM)

10/10 Exceptional! (52 reviews)

Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities.

Reviewed on Dec 29, 2025

![Cliff House Maine](https://images.trvl-media.com/lodging/4000000/3990000/3981200/3981160/eb122fc0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cliff House Maine

Bald Head

CA $2,251

per person

Apr 19 - Apr 25

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Portland (PWM)

9.4/10 Exceptional! (1,001 reviews)

Great hotel with super nice views!

Reviewed on Mar 1, 2026

![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/1a7f326f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Portland Harbor Hotel

Downtown Portland

CA $1,677

per person

May 16 - May 23

found 12 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Portland (PWM)

9.2/10 Wonderful! (1,765 reviews)

Nice place, clean room, courteous staff, NO FREE PARKING! :(

Reviewed on Feb 28, 2026

![The Weldon Hotel](https://images.trvl-media.com/lodging/108000000/107330000/107321700/107321604/38875013_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Weldon Hotel

Downtown Portland

CA $1,010

per person

Apr 19 - Apr 25

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Portland (PWM)

9.8/10 Exceptional! (86 reviews)

Location is excellent. Short walking distance to every good restaurant and shop. The property was very nice and clean. The kitchen is very well equipped. The gym is very good sized for the size of the apartment building with 13 units in it. The management’s communication was prompt and friendly and responded to all of our wishes. However, the place is advertised as a hotel, but don’t expect services as in a hotel. It resembles more a short term rental home - no cleaning service and no lobby. Otherwise everything was very nice in the apartment and we had a great time.

Reviewed on Jan 3, 2026

![The Docent's Collection at 121 Middle Street](https://images.trvl-media.com/lodging/39000000/38780000/38770100/38770068/148140d6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Docent's Collection at 121 Middle Street

Downtown Portland

CA $1,141

per person

Apr 19 - Apr 25

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Portland (PWM)

9.6/10 Exceptional! (273 reviews)

Check-in and check-out are a breeze, easy access to a city parking lot on the block (needed as there was a snow ban on parking when I visited!). In terms of the space itself - clean, well appointed, spacious. Honestly a treat to stay here!

Reviewed on Feb 23, 2026

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_6046825)

## Ready to book your vacation to Bailey Island?

Choose your dates

## Bailey Island Hotel Deals

![The Westin Portland Harborview](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/c479d2b6_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Westin Portland Harborview

157 High St Portland ME

Fully refundableReserve now, pay when you stay

CA $134

CA $148 total

Mar 29 - Mar 30

includes taxes & fees

8.8/10 Excellent! (1,004 reviews)

The room was very clean, check in and out was easy, parking was affordable.

Reviewed on Mar 3, 2026

[](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=6273&PinnedHotelID=6273&HadPinnedHotel=true&regionId=6046825)

![Clarion Hotel Portland Airport ME](https://images.trvl-media.com/lodging/1000000/10000/7200/7171/c90266f6_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Fully refundableReserve now, pay when you stay

CA $105

CA $117 total

Mar 24 - Mar 25

includes taxes & fees

8/10 Very Good! (1,391 reviews)

Love this place pool and hot tub very clean wish the Jett’s hear behind your back instead of up from bottom of tub but you get your moneys worth

Reviewed on Mar 4, 2026

[](https://expedia.ca/Hotel-Search?startDate=24%2F03%2F2026&endDate=25%2F03%2F2026&selected=7171&PinnedHotelID=7171&HadPinnedHotel=true&regionId=6046825)

![Cambria Hotel Portland Downtown-Old Port](https://images.trvl-media.com/lodging/78000000/77990000/77981700/77981687/2540bb39_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Cambria Hotel Portland Downtown-Old Port

25 HANCOCK STREET Portland ME

Fully refundable

CA $125

CA $175 total

Mar 26 - Mar 27

includes taxes & fees

9.4/10 Exceptional! (1,168 reviews)

Easy check in and friendly staff. Food was good room was big and with nice view.

Reviewed on Mar 2, 2026

[](https://expedia.ca/Hotel-Search?startDate=26%2F03%2F2026&endDate=27%2F03%2F2026&selected=77981687&PinnedHotelID=77981687&HadPinnedHotel=true&regionId=6046825)

[See all 1,764 properties in Bailey Island](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=05%2F03%2F2026&endDate=06%2F03%2F2026&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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- [Kk Leisure Rental Cars in Casco Bay Islands ](https://www.expedia.ca/KK-Leisure-Car-Rentals-In-Casco-Bay-Islands.d553248621532668098-c1133.Car-Rental-Guide-Suppliers)
- [National Car Rental Rental Cars in Great Island ](https://www.expedia.ca/National-Car-Rental-Car-Rentals-In-Great-Island.d553248635976193455-c42.Car-Rental-Guide-Suppliers)
- [Thai Cars Rental Cars in Casco Bay Islands ](https://www.expedia.ca/Thai-Cars-Car-Rentals-In-Casco-Bay-Islands.d553248621532668098-c1027.Car-Rental-Guide-Suppliers)

- [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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