Title: Bailey Island Vacation Rentals from $103: Search Short-Term Rentals | Expedia.com

[Bailey Island Travel Guide](https://expedia.com/Bailey-Island.dx6046825)[Hotels in Bailey Island](https://expedia.com/Bailey-Island-Hotels.d6046825.Travel-Guide-Hotels)[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)

![](https://images.trvl-media.com/place/6046825/3641ac6e-a5fc-4f22-a47d-0c23ea40681b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6046825/3641ac6e-a5fc-4f22-a47d-0c23ea40681b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=6046825&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=6046825&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=6046825&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 17 - Jul 19](https://www.expedia.com/Hotel-Search?regionId=6046825&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Bailey Island vacation rentals

![Desk, laptop workspace, free WiFi](https://images.trvl-media.com/lodging/121000000/120690000/120687300/120687259/72fd64d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, free WiFi](https://images.trvl-media.com/lodging/121000000/120690000/120687300/120687259/ae36bb84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120690000/120687300/120687259/dc500751.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior detail](https://images.trvl-media.com/lodging/121000000/120690000/120687300/120687259/cd809bb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### HomeAwhile

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

Scarborough

9.6/10

Exceptional

(11 reviews)

"The room was spotless. The hotel was very clean and the staff was very friendly and helpful."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Monique

$95 nightly

$103 total

Apr 19 - Apr 20

Total with taxes and fees

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

![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93546700/93546665/35b31893.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93546700/93546665/541aa35d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93546700/93546665/01004b4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93546700/93546665/e6c45cb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful Waterfront Apt w/ Deck, 22 Mi to Portland

[](https://www.expedia.com/Freeport-Hotels-Peaceful-Waterfront-Apt-Wdeck.h93546665.Hotel-Information)

Freeport

[](https://www.expedia.com/Freeport-Hotels-Peaceful-Waterfront-Apt-Wdeck.h93546665.Hotel-Information)

![Deluxe Suite, 1 King Bed | Private kitchen | Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107330000/107321700/107321604/9fd24e5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio Suite, 1 King Bed | Premium bedding, in-room safe, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/108000000/107330000/107321700/107321604/b6c98e29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite, 1 King Bed | Living area | LCD TV, Netflix, streaming services, music library](https://images.trvl-media.com/lodging/108000000/107330000/107321700/107321604/3eb6def3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite, 2 Bedrooms | Private kitchen | Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107330000/107321700/107321604/6c222be1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Weldon Hotel

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

Downtown Portland

9.8/10

Exceptional

(98 reviews)

"The hotel is in an ideal location in downtown Portland. The staff is so kind and very accommodating! The stay was beyond comfortable and is the place we will stay every time we return to Portland!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lauren

$237 nightly

$251 total

Apr 13 - Apr 14

Total with taxes and fees

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

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.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-04-11&endDate=2026-04-12&regionId=6046825&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Bailey+Island%2C+Maine%2C+United+States+of+America&regionId=6046825&latLong=43.736694%2C-69.994064&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=CABIN)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Bailey+Island%2C+Maine%2C+United+States+of+America&regionId=6046825&latLong=43.736694%2C-69.994064&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=COTTAGE)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Bailey+Island%2C+Maine%2C+United+States+of+America&regionId=6046825&latLong=43.736694%2C-69.994064&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=VACATION_HOME)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Bailey+Island%2C+Maine%2C+United+States+of+America&regionId=6046825&latLong=43.736694%2C-69.994064&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=APART_HOTEL)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Bailey+Island%2C+Maine%2C+United+States+of+America&regionId=6046825&latLong=43.736694%2C-69.994064&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=CONDO)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Bailey+Island%2C+Maine%2C+United+States+of+America&regionId=6046825&latLong=43.736694%2C-69.994064&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=APARTMENT)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Bailey+Island%2C+Maine%2C+United+States+of+America&regionId=6046825&latLong=43.736694%2C-69.994064&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=VILLA)

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## Top Bailey Island Hotel Reviews

![Tru by Hilton Portland Airport Area](https://images.trvl-media.com/lodging/19000000/18960000/18952900/18952854/627581df_y.jpg)

### Tru by Hilton Portland Airport Area

8/10 Good

"When staying for more than 2 days, must request housekeeping to replenish your room towels if not they will not, learned by experience!!😢😟"

[](https://expedia.com/Portland-Hotels-Tru-By-Hilton-Portland-Airport-Area.h18952854.Hotel-Information)

![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/1a7f326f_y.jpg)

### Portland Harbor Hotel

6/10 Okay

"We paid a little extra for a room with a Courtyard view. What we got was a 2nd floor room as far as possible from the elevator and when I pulled back the curtains I was looking at a giant kitchen exhaust fan that gave us a constant deep buzz in the room. The hotel did not seem busy and this room is literally the only Courtyard room with a giant exhaust stack only feet outside the window. Don't know why we were given literally the worst room available in that category. But I do know that I will avoid this group of hotels from now on. "

[](https://expedia.com/Portland-Hotels-Portland-Harbor-Hotel.h898621.Hotel-Information)

![DoubleTree by Hilton Hotel Portland](https://images.trvl-media.com/lodging/1000000/10000/8200/8166/17e160ed_y.jpg)

### DoubleTree by Hilton Hotel Portland

10/10 Excellent

"Pool was nice. Very convenient to shopping, restaurants & activities. Great price for what you get. "

[](https://expedia.com/Portland-Hotels-DoubleTree-By-Hilton-Hotel-Portland.h8166.Hotel-Information)

![Portland Regency Hotel & Spa](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/d87c36dc_y.jpg)

### Portland Regency Hotel & Spa

8/10 Good

"Easy check in and valet. Room was clean. While the sauna, Steam and hot tub were nice, if you look too close it doesn't appear to get regular cleaning(floors were not very clean in hot tub area)"

[](https://expedia.com/Portland-Hotels-Portland-Regency-Hotel-Spa.h920050.Hotel-Information)

![Cambria Hotel Portland Downtown-Old Port](https://images.trvl-media.com/lodging/78000000/77990000/77981700/77981687/2540bb39_y.jpg)

### Cambria Hotel Portland Downtown-Old Port

10/10 Excellent

"Very nice and clean room. Staff was very friendly and helpful. Overall great stay."

[](https://expedia.com/Portland-Hotels-Cambria-Hotel-Portland-Downtown-Old-Port.h77981687.Hotel-Information)

![Holiday Inn Portland-By the Bay by IHG](https://images.trvl-media.com/lodging/1000000/20000/12000/11991/4e5dab1b_y.jpg)

### Holiday Inn Portland-By the Bay by IHG

10/10 Excellent

"Clean room, comfy bed, nice breakfast bar."

[](https://expedia.com/Portland-Hotels-Holiday-Inn-Portland-By-The-Bay.h11991.Hotel-Information)

![Canopy by Hilton Portland Waterfront](https://images.trvl-media.com/lodging/65000000/64480000/64474900/64474828/419cdab1_y.jpg)

### Canopy by Hilton Portland Waterfront

10/10 Excellent

"Nice room, staff was very nice and welcoming. Nice bar area"

[](https://expedia.com/Portland-Hotels-Canopy-By-Hilton-Portland-Waterfront.h64474828.Hotel-Information)

![The Westin Portland Harborview](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/c479d2b6_y.jpg)

### The Westin Portland Harborview

10/10 Excellent

"I frequently stay at this property. It is a very clean property with kind and helpful staff and an excellent restaurant and spa. I was locked out of the next door parking garage and Dan (door man?) helped me get my car out. He ran out there in the freezing cold, called the garage mgmt and got me out. Dan deserves a raise."

[](https://expedia.com/Portland-Hotels-The-Westin-Portland-Harborview.h6273.Hotel-Information)

![Inn at St John Portland In-Town](https://images.trvl-media.com/lodging/1000000/70000/67500/67481/c8f4e76e_y.jpg)

### Inn at St John Portland In-Town

10/10 Excellent

"Great place, great location, great breakfast, great service, probably the best place to stay in Portland, a real gem!"

[](https://expedia.com/Portland-Hotels-Inn-At-St-John-Portland-In-Town.h67481.Hotel-Information)

## Find out more about Bailey Island

**Everything you need to know about Bailey Island vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Bailey Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Bailey Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Bailey Island vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Bailey Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Bailey Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $103 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Bailey Island rentals**

At Expedia, we put the best Bailey Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Bailey Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Bailey Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Bailey Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

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- [Vacation Homes in Bailey Island ](https://expedia.com/Bailey-Island-Private-Vacation-Homes.d6046825-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Bailey Island ](https://expedia.com/Bailey-Island-Apartments.d6046825-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Bailey Island ](https://expedia.com/Bailey-Island-Cottages.d6046825-aaCottages.Travel-Guide-Accommodation)
- [Condo Rentals in Bailey Island ](https://expedia.com/Bailey-Island-Condos.d6046825-aaCondos.Travel-Guide-Accommodation)
- [Cabin Rentals in Bailey Island ](https://expedia.com/Bailey-Island-Cabins.d6046825-aaCabins.Travel-Guide-Accommodation)
- [B&B in Bailey Island ](https://expedia.com/Bailey-Island-Bed-And-Breakfast.d6046825-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Lodges in Bailey Island ](https://expedia.com/Bailey-Island-Lodges.d6046825-aaLodges.Travel-Guide-Accommodation)
- [Aparthotels in Bailey Island ](https://expedia.com/Bailey-Island-Apart-Hotels.d6046825-aaApartHotels.Travel-Guide-Accommodation)
- [Motels in Bailey Island ](https://expedia.com/Bailey-Island-Motels.d6046825-aaMotels.Travel-Guide-Accommodation)
- [Guest Houses in Bailey Island ](https://expedia.com/Bailey-Island-Guest-Houses.d6046825-aaGuestHouses.Travel-Guide-Accommodation)
- [Farmstay in Bailey Island ](https://expedia.com/Bailey-Island-Agritourism.d6046825-aaAgritourism.Travel-Guide-Accommodation)
- [Inns in Bailey Island ](https://expedia.com/Bailey-Island-Inns.d6046825-aaInns.Travel-Guide-Accommodation)
- [Villas in Bailey Island ](https://expedia.com/Bailey-Island-Villas.d6046825-aaVillas.Travel-Guide-Accommodation)
- [RV Parks in Bailey Island ](https://expedia.com/Bailey-Island-RV-Parks.d6046825-aaRVParks.Travel-Guide-Accommodation)
- [Castles in Bailey Island ](https://expedia.com/Bailey-Island-Castles.d6046825-aaCastles.Travel-Guide-Accommodation)

## Frequently asked questions

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- [Portland Oceanfront Hotels](https://expedia.com/Portland-Hotels-Oceanfront-Hotels.0-0-d181420-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Best Hotels in Portland](https://expedia.com/Portland-Hotels.d181420.Travel-Guide-Hotels)
- [Best Hotels in Wells](https://expedia.com/Wells-Hotels.d56045.Travel-Guide-Hotels)
- [Best Hotels in Old Orchard Beach](https://expedia.com/Old-Orchard-Beach-Hotels.d9256.Travel-Guide-Hotels)
- [York Beach Oceanfront Hotels](https://expedia.com/York-Beach-Hotels-Oceanfront-Hotels.0-0-d183307-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Best Hotels in Freeport](https://expedia.com/Freeport-Hotels.d180773.Travel-Guide-Hotels)
- [Portland Cheap Hotels](https://expedia.com/Portland-Hotels-Cheap-Hotels.0-0-d181420-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Best Hotels in Augusta](https://expedia.com/Augusta-Hotels.d452.Travel-Guide-Hotels)
- [Best Hotels in South Portland](https://expedia.com/South-Portland-Hotels.d6769.Travel-Guide-Hotels)
- [Best Hotels in Rockland](https://expedia.com/Rockland-Hotels.d3004.Travel-Guide-Hotels)

Flights

- [Flights to BGR](https://expedia.com/Cheap-Flights-To-Bangor.d6050918.Travel-Guide-Flights)
- [Flights to PWM](https://expedia.com/Cheap-Flights-To-Portland.d181420.Travel-Guide-Flights)
- [Flights to AUG](https://expedia.com/Cheap-Flights-To-Bar-Harbor.d561.Travel-Guide-Flights)

Cars

- [Car rentals in Bangor](https://expedia.com/Car-Rentals-In-Bangor.d6050918.Car-Rental-Guide)
- [Car rentals in Portland](https://expedia.com/Car-Rentals-In-Portland.d181420.Car-Rental-Guide)

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