Title: Visit Bailey Island: 2026 Travel Guide for Bailey Island, Maine | Expedia.com

[Hotels in Bailey Island](https://expedia.com/Bailey-Island-Hotels.d6046825.Travel-Guide-Hotels)[Vacation Rentals in Bailey Island](https://expedia.com/Bailey-Island-Vacation-Rentals.d6046825.Travel-Guide-VacationRentals)[Flights to Bailey Island](https://expedia.com/Cheap-Flights-To-Bailey-Island.d6046825.Travel-Guide-Flights)[Car Rentals in Bailey Island](https://expedia.com/Car-Rentals-In-Bailey-Island.d6046825.Car-Rental-Guide)[Bailey Island Vacation Packages](https://expedia.com/Bailey-Island.d6046825.Destination-Travel-Guides)

# Bailey Island, ME

## Travel Guide

![Bailey Island featuring rugged coastline and a house](https://images.trvl-media.com/place/6046825/7787ff8e-ec8a-4628-8f3d-1af96a802dbe.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Bailey Island featuring rugged coastline and a house](https://images.trvl-media.com/place/6046825/7787ff8e-ec8a-4628-8f3d-1af96a802dbe.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Bailey Island showing general coastal views](https://images.trvl-media.com/place/6046825/0100dace-c0d9-41dd-bce2-1b343a475e84.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Bailey Island which includes general coastal views](https://images.trvl-media.com/place/6046825/3641ac6e-a5fc-4f22-a47d-0c23ea40681b.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Bailey Island showing signage](https://images.trvl-media.com/place/6046825/41d6e214-891f-454e-940e-7ba3adcf5af9.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

## Visit Bailey Island

Things to do

#### Try to resist marooning yourself forever on this serene bit of land that features beaches, hikes and a lively community.

Bailey Island is prototypical Maine, with rocky beaches, gruff lobster fishermen and small-town charm that epitomize the Pine Tree State. First settled by the son of a freed slave, William Black, the island is named after Reverend Thomas Bailey. Look down when driving over the Bailey Island Bridge to spot Will’s Gut, the spit separating Orr’s Island and Bailey Island and named for its original inhabitant.

Pause at the opposite side of the bridge for a look at the bridge itself, a nationally recognized historic landmark, a rare cribstone bridge that allows the tides to pass through its structure. Drive to Mackerel Cove for the picture-postcard Maine settlement with small houses and lobster fishing boats bobbing on the edge of Casco Bay. Continue to the end of the island, Land’s End, and let the spray cool you down in the warmer months as you gaze across the sea. Buoys bobbing in the water indicate locations of lobster cages.

Hike along the short Giant’s Stairs Trail to learn about the varied geology of Bailey Island. Climb down huge black stones, so different from surrounding rocks, and look for flecks of garnet and quartz.

Bailey Island is part of Harpswell, with a town council governed by popular vote, creating a strong sense of community. Bailey Island’s community center and main event space is the Bailey Island Library Hall. Stop by for an event or simply to see this historic building where the famous psychoanalyst Carl Jung gave an early American lecture.

Drive to Bailey Island in 1 hour from Portland, Maine. Boat tours from Portland also occasionally come out to Harpswell and its more than 200 islands. Portland has an international airport serving numerous locations and is just 90 minutes by car from Boston. Harspwell does not have public transportation, so rent or bring a car.

Bailey Island is the perfect place for a Maine getaway, whether you are locals, frequent visitors or have never been to this beautiful part of the world.

![](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.com/deals?rfrr=DX_SPRING_PROMO_6046825)

- Bailey Island Hotel Deals
- Vacation Rentals in Bailey Island

![The Westin Portland Harborview](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/67608060_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Westin Portland Harborview

157 High St Portland ME

$98 nightly

$108 total

Mar 15 - Mar 16

Total with taxes and fees

Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...

8.8/10 Excellent! (1,007 reviews)

Location, clean rooms, pleasant staff

Reviewed on Feb 23, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F15%2F2026&endDate=3%2F16%2F2026&selected=6273&PinnedHotelID=6273&HadPinnedHotel=true&regionId=6046825)

![Clarion Hotel Portland Airport ME](https://images.trvl-media.com/lodging/1000000/10000/7200/7171/b163ad24_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

$77 nightly

$85 total

Mar 5 - Mar 6

Total with taxes and fees

Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...

8/10 Very Good! (1,380 reviews)

Comfortable bed and pillows. Disappointed that the airport shuttle started running so late and we had to pay for Uber ride for morning flight. Those hours maybe should be listed. Otherwise nice.

Reviewed on Feb 24, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F5%2F2026&endDate=3%2F6%2F2026&selected=7171&PinnedHotelID=7171&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

$151 nightly

$167 total

Mar 4 - Mar 5

Total with taxes and fees

Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff ...

9.2/10 Wonderful! (1,776 reviews)

Location was great, staff was friendly (especially adam at the front desk) but the bed was very uncomfortable, pillows were cheap and deflated, and the whole "resort fee" was very offputting. I would rather just be told a real rate when I book over getting an extra few hundred in charges. The 35$ ...

Reviewed on Feb 23, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F4%2F2026&endDate=3%2F5%2F2026&selected=898621&PinnedHotelID=898621&HadPinnedHotel=true&regionId=6046825)

[See all 1,759 properties in Bailey Island](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=2%2F26%2F2026&endDate=2%2F27%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.

![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

Book a stay at this beach vacation home in Bailey Island. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Cobwork Bridge and Mackerel Cove ...

10/10 Exceptional! (234 reviews)

Wonderful house. Well equipped. Gorgeous view.

Reviewed on Nov 29, 2025

[](https://expedia.com/Bailey-Island-Hotels-New-Cottage-Perfect-For-A-Peaceful-And-Quiet-Stay-On-The-Ocean-With-Beach.h27118287.Hotel-Information)

![The Weldon Hotel](https://images.trvl-media.com/lodging/108000000/107330000/107321700/107321604/38875013_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Weldon Hotel

54 York St Portland ME

Book a stay at this luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Victoria Mansion and ...

9.8/10 Exceptional! (93 reviews)

Great rooms and furnishings

Reviewed on Feb 16, 2026

[](https://expedia.com/Portland-Hotels-The-Weldone-Hotel.h107321604.Hotel-Information)

![HomeAwhile](https://images.trvl-media.com/lodging/121000000/120690000/120687300/120687259/d41dd716_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

HomeAwhile

205 Southborough Drive Scarborough ME

Stay at this aparthotel in Scarborough. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Maine Mall and Nonesuch River Golf Club are ...

[](https://expedia.com/Scarborough-Hotels-HomeAwhile.h120687259.Hotel-Information)

[See all properties in Bailey Island](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&regionId=6046825&sort=VACATION_RENTAL)

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.

## Check Bailey Island hotel availability

[Tonight

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[Tomorrow night

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[This weekend

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[Next weekend

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6046825&startDate=3%2F6%2F2026&endDate=3%2F8%2F2026)[Mar 6 - Mar 8](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6046825&startDate=3%2F6%2F2026&endDate=3%2F8%2F2026)

### Popular places to visit

#### Bailey Island Bridge

4.5/5(9 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. 

[](https://expedia.com/Bailey-Island-Bridge-Bailey-Island.d6077256.Vacation-Attraction)

#### Land's End Gift Shop

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. 

[](https://expedia.com/Lands-End-Gift-Shop-Bailey-Island.d553248621532668102.Vacation-Attraction)

#### Cobwork Bridge

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. 

[](https://expedia.com/Cobwork-Bridge-Bailey-Island.d553248621532668105.Vacation-Attraction)

## Cities near Bailey Island

![Shellfish farm on Orr's Island, Harpswell, Maine, United States.](https://images.trvl-media.com/place/3000440072/d2ea8e7f-dfa9-47e3-b097-23c6ce2e1cf0.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Orrs Island

![Fishing boats, old and new, a lobster shack, and scattered trap floats fill the harbor scene at Mackerel Cove on Bailey Island at the tip of the rocky Harpswell Peninsula of Down East Maine.](https://images.trvl-media.com/place/553248635077688915/4b7aaa83-2c02-4718-97a4-a5815ab864be.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Harpswell

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- [Bailey Island Bridge ](https://www.expedia.com/Bailey-Island-Bridge-Bailey-Island.d6077256.Vacation-Attraction)
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- [Visit Casco Bay Islands ](https://www.expedia.com/Casco-Bay-Islands.dx553248621532668098)
- [Visit Cundys Harbor ](https://www.expedia.com/Cundys-Harbor.dx3000439764)
- [Casco Bay Islands Vacations ](https://www.expedia.com/Casco-Bay-Islands.d553248621532668098.Destination-Travel-Guides)
- [Visit Harpswell ](https://www.expedia.com/Harpswell.dx553248635077688915)
- [Cundys Harbor Vacations ](https://www.expedia.com/Cundys-Harbor.d3000439764.Destination-Travel-Guides)
- [Visit Sebasco Estates ](https://www.expedia.com/Sebasco-Estates.dx180774)
- [Visit Hermit Island ](https://www.expedia.com/Hermit-Island.dx6341836)
- [Little John Island Preserve ](https://www.expedia.com/Little-John-Island-Preserve-Yarmouth.d553248621532668101.Vacation-Attraction)
- [Sebasco Estates Vacations ](https://www.expedia.com/Sebasco-Estates.d180774.Destination-Travel-Guides)

- [Car rentals near Orrs Island ](https://www.expedia.com/Car-Rentals-In-Orrs-Island.d3000440072.Car-Rental-Guide)
- [Car rentals near Harpswell Center ](https://www.expedia.com/Car-Rentals-In-Harpswell-Center.d553248635975848499.Car-Rental-Guide)
- [Car rentals near Chebeague Island ](https://www.expedia.com/Car-Rentals-In-Chebeague-Island.d6046986.Car-Rental-Guide)
- [Car rentals near Bustins Island ](https://www.expedia.com/Car-Rentals-In-Bustins-Island.d553248635976478507.Car-Rental-Guide)
- [Car rentals near Cundys Harbor ](https://www.expedia.com/Car-Rentals-In-Cundys-Harbor.d3000439764.Car-Rental-Guide)
- [Car rentals near Harpswell ](https://www.expedia.com/Car-Rentals-In-Harpswell.d553248635077688915.Car-Rental-Guide)
- [Island Car Rentals Rental Cars in Harpswell ](https://www.expedia.com/Island-Car-Rentals-Car-Rentals-In-Harpswell.d553248635077688915-c1132.Car-Rental-Guide-Suppliers)
- [Convertible Car Rentals in Harpswell ](https://www.expedia.com/Convertible-Car-Rentals-In-Harpswell.d553248635077688915-tConvertible.Car-Rental-Guide-Class)
- [Avis Canaries Rental Cars in Harpswell ](https://www.expedia.com/Avis-Canaries-Car-Rentals-In-Harpswell.d553248635077688915-c1135.Car-Rental-Guide-Suppliers)
- [Car rentals near Sebasco ](https://www.expedia.com/Car-Rentals-In-Sebasco.d553248635975749228.Car-Rental-Guide)
- [Car rentals near Sebasco Estates ](https://www.expedia.com/Car-Rentals-In-Sebasco-Estates.d180774.Car-Rental-Guide)

- [Orrs Island Vacation Rentals ](https://www.expedia.com/Orrs-Island-Vacation-Rentals.d3000440072.Travel-Guide-VacationRentals)
- [Chebeague Island Vacation Rentals ](https://www.expedia.com/Chebeague-Island-Vacation-Rentals.d6046986.Travel-Guide-VacationRentals)
- [Casco Bay Islands Vacation Rentals ](https://www.expedia.com/Casco-Bay-Islands-Vacation-Rentals.d553248621532668098.Travel-Guide-VacationRentals)

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

- Cities near Bailey Island
- Places of interest

[Orrs Island](https://expedia.com/Orrs-Island.dx3000440072)[Harpswell](https://expedia.com/Harpswell.dx553248635077688915)

- [Bailey Island Bridge ](https://expedia.com/Bailey-Island-Bridge-Bailey-Island.d6077256.Vacation-Attraction)
- [Land's End Gift Shop ](https://expedia.com/Lands-End-Gift-Shop-Bailey-Island.d553248621532668102.Vacation-Attraction)
- [Cobwork Bridge ](https://expedia.com/Cobwork-Bridge-Bailey-Island.d553248621532668105.Vacation-Attraction)
- [Acadia National Park ](https://expedia.com/Acadia-National-Park-Maine.d6129938.Vacation-Attraction)
- [Maine Mall ](https://expedia.com/Maine-Mall-South-Portland.d6077232.Vacation-Attraction)
- [Thompson's Point ](https://expedia.com/Thompsons-Point-Portland.d553248622839373742.Vacation-Attraction)
- [LL Bean Flagship Store ](https://expedia.com/LL-Bean-Flagship-Store-Freeport.d6180409.Vacation-Attraction)
- [State Theatre ](https://expedia.com/State-Theatre-Downtown-Portland.d553248621532668181.Vacation-Attraction)
- [Maine Medical Center ](https://expedia.com/Maine-Medical-Center-Valley-Street.d553248622839377923.Vacation-Attraction)
- [Cross Insurance Arena ](https://expedia.com/Cross-Insurance-Arena-Downtown-Portland.d6077236.Vacation-Attraction)
- [Higgins Beach ](https://expedia.com/Higgins-Beach-Maine.d6326755.Vacation-Attraction)
- [Portland Head Light ](https://expedia.com/Portland-Head-Light-Cape-Elizabeth.d6077212.Vacation-Attraction)
- [Bowdoin College ](https://expedia.com/Bowdoin-College-Brunswick.d6186042.Vacation-Attraction)
- [Coastal Maine Botanical Gardens ](https://expedia.com/Coastal-Maine-Botanical-Gardens-Boothbay.d6186125.Vacation-Attraction)
- [University of New England ](https://expedia.com/University-Of-New-England-Portland.d6176269.Vacation-Attraction)
- [Merrill Auditorium ](https://expedia.com/Merrill-Auditorium-Downtown-Portland.d6077222.Vacation-Attraction)
- [Portland Museum of Art ](https://expedia.com/Portland-Museum-Of-Art-Downtown-Portland.d6077214.Vacation-Attraction)
- [Popham Beach ](https://expedia.com/Popham-Beach-Phippsburg.d553248635077137344.Vacation-Attraction)
- [Casco Bay ](https://expedia.com/Casco-Bay-Maine.d553248635056399288.Vacation-Attraction)
- [University of Southern Maine ](https://expedia.com/University-Of-Southern-Maine-Oakdale.d6077216.Vacation-Attraction)
- [Boothbay Harbor Marina ](https://expedia.com/Boothbay-Harbor-Marina-Boothbay-Harbor.d6186217.Vacation-Attraction)
- [East End Beach ](https://expedia.com/East-End-Beach-East-End.d6326357.Vacation-Attraction)
- [Hadlock Field ](https://expedia.com/Hadlock-Field-Valley-Street.d6077238.Vacation-Attraction)
- [Cape Elizabeth Light ](https://expedia.com/Cape-Elizabeth-Light-Cape-Elizabeth.d553248621532668166.Vacation-Attraction)
- [Scarborough Beach State Park ](https://expedia.com/Scarborough-Beach-State-Park-Scarborough.d6327764.Vacation-Attraction)
- [Casco Bay Lines Ferry Terminal ](https://expedia.com/Casco-Bay-Lines-Ferry-Terminal-Downtown-Portland.d553248621533120972.Vacation-Attraction)
- [Children's Museum and Theatre of Maine ](https://expedia.com/Childrens-Museum-And-Theatre-Of-Maine-Portland.d6326315.Vacation-Attraction)
- [Desert of Maine ](https://expedia.com/Desert-Of-Maine-Freeport.d6190010.Vacation-Attraction)
- [Willard Beach ](https://expedia.com/Willard-Beach-Willard-Beach.d6077248.Vacation-Attraction)
- [Eastern Promenade ](https://expedia.com/Eastern-Promenade-East-End.d6326369.Vacation-Attraction)
- [Cabbage Island ](https://expedia.com/Cabbage-Island-Maine.d6334497.Vacation-Attraction)

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