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

![TV](https://images.trvl-media.com/lodging/103000000/102830000/102829300/102829282/dbe85b25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/103000000/102830000/102829300/102829282/8b898836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102830000/102829300/102829282/fc36ebbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102830000/102829300/102829282/9f336acb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2 bedroom w/ expansive water views

[](https://www.expedia.com/Phippsburg-Hotels-Escape-To-Positive-Outlook.h102829282.Hotel-Information)

West Point

10/10

Exceptional

(3 reviews)

"The host was welcoming. The home was clean, comfortable and the views were outstanding. "

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

Rachel K.

$204 nightly

$216 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Phippsburg-Hotels-Escape-To-Positive-Outlook.h102829282.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/104000000/103490000/103484100/103484035/w505h683x260y0-13655fb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103490000/103484100/103484035/w948h683x38y0-5668c518.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/104000000/103490000/103484100/103484035/w905h683x59y0-fcd81b07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/104000000/103490000/103484100/103484035/w506h683x259y0-14532eeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern style in historic building in downtown Bath

[](https://www.expedia.com/Bath-Hotels-Modern-Style-In-Historic-Building-In-Downtown-Bath.h103484035.Hotel-Information)

Bath

10/10

Exceptional

(8 reviews)

"Such a great location! We could easily walk all over the cute downtown."

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

Keisha C.

$203 nightly

$221 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Bath-Hotels-Modern-Style-In-Historic-Building-In-Downtown-Bath.h103484035.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/70000000/69340000/69337600/69337504/b1bdd4cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/70000000/69340000/69337600/69337504/0a77c82a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/70000000/69340000/69337600/69337504/5456fd4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/70000000/69340000/69337600/69337504/43f447da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

[](https://www.expedia.com/Boothbay-Harbor-Hotels-Large-Guest-Suite-With-Private-Bath-On-Quiet-Street-Near-Bowdoin-College.h69337504.Hotel-Information)

Brunswick

10/10

Exceptional

(147 reviews)

"Lovely space, comfortable bed, very convenient to downtown Brunswick."

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

Kimberly G.

$110 nightly

$120 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Boothbay-Harbor-Hotels-Large-Guest-Suite-With-Private-Bath-On-Quiet-Street-Near-Bowdoin-College.h69337504.Hotel-Information)

![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)

![Interior detail](https://images.trvl-media.com/lodging/121000000/120690000/120687300/120687259/cd809bb5.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)

![Reception](https://images.trvl-media.com/lodging/121000000/120690000/120687300/120687259/d41dd716.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### HomeAwhile

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

Scarborough

9.4/10

Exceptional

(10 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 17 - Apr 18

Total with taxes and fees

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

![Property grounds](https://images.trvl-media.com/lodging/125000000/124250000/124249600/124249581/710607f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124250000/124249600/124249581/c12a4081.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124250000/124249600/124249581/2f958b81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124250000/124249600/124249581/d67a8ca9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pond Cabin: Private Sauna+Near Beach+FirePit+Pond

[](https://www.expedia.com/Georgetown-Hotels-Private-SaunaNear-BeachFirePitForest-ViewPond.h124249581.Hotel-Information)

Georgetown

$418 nightly

$446 total

Apr 27 - Apr 28

Total with taxes and fees

[](https://www.expedia.com/Georgetown-Hotels-Private-SaunaNear-BeachFirePitForest-ViewPond.h124249581.Hotel-Information)

![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/103000000/102830000/102829300/102829284/ac74d9c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/103000000/102830000/102829300/102829284/08f71e1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/103000000/102830000/102829300/102829284/w790h591x5y5-ff173a23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102830000/102829300/102829284/0b84a256.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fantastic Waterfront Views

[](https://www.expedia.com/Phippsburg-Hotels-Fantastic-Waterfront-Views.h102829284.Hotel-Information)

West Point

9.8/10

Exceptional

(16 reviews)

"The location and views were incredible. Quiet and relaxing spot."

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

Vanessa W.

$262 nightly

$265 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Phippsburg-Hotels-Fantastic-Waterfront-Views.h102829284.Hotel-Information)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124250000/124249600/124249582/8edf1966.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/125000000/124250000/124249600/124249582/64493aba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/125000000/124250000/124249600/124249582/772c9105.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124250000/124249600/124249582/505a1fc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spruce Studio: Near Beach+FirePit+Pond+Heat/AC+Fast WiFi

[](https://www.expedia.com/Georgetown-Hotels-State-Park-BeachFirePitPondHeatACFast-WiFi.h124249582.Hotel-Information)

Georgetown

10/10

Exceptional

(2 reviews)

"Really lovely cabin with all the amenities within a stone’s throw to amazing trails and beaches. Would love to come back!"

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

Palmer M.

$320 nightly

$338 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Georgetown-Hotels-State-Park-BeachFirePitPondHeatACFast-WiFi.h124249582.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34150000/34141000/34140995/252d6dc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books](https://images.trvl-media.com/lodging/35000000/34150000/34141000/34140995/68a7a155.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34150000/34141000/34140995/69ad9bd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34150000/34141000/34140995/861529a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Camp Forever cottage

[](https://www.expedia.com/Harpswell-Hotels-Camp-Forever-Cottage.h34140995.Hotel-Information)

Harpswell

9.6/10

Exceptional

(58 reviews)

"Everything was great, fantastic location!"

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

Dennis H.

$308 nightly

$336 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/Harpswell-Hotels-Camp-Forever-Cottage.h34140995.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/28000000/27540000/27534000/27533976/59add01a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/28000000/27540000/27534000/27533976/w2016h1286x0y0-21928c11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/28000000/27540000/27534000/27533976/0a867dc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/28000000/27540000/27534000/27533976/46f0eb26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2King Bed BR Private Apt Downtown Brunswick

[](https://www.expedia.com/Boothbay-Harbor-Hotels-2king-Bed-BR-Private-Apt-Downtown-Brunswick.h27533976.Hotel-Information)

Brunswick

8.4/10

Very Good

(11 reviews)

"Small place in a great location. Easily walk to several shops and restaurants. "

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

Jillian B.

$216 nightly

$235 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/Boothbay-Harbor-Hotels-2king-Bed-BR-Private-Apt-Downtown-Brunswick.h27533976.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/96000000/95170000/95164500/95164446/48575d8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/96000000/95170000/95164500/95164446/26983b0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95170000/95164500/95164446/d2de73a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/96000000/95170000/95164500/95164446/d6a93002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern, Luxurious, Cabin in the Woods - 17

[](https://www.expedia.com/Freeport-Hotels-Modern.h95164446.Hotel-Information)

Freeport

10/10

Exceptional

(3 reviews)

"Awesome camping in a great, quiet campground. The staff is very responsive and all the little details make this place special."

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

Miranda K.

$261 nightly

$284 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Freeport-Hotels-Modern.h95164446.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/72000000/71550000/71542100/71542068/0f41a861.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/72000000/71550000/71542100/71542068/a0a928af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/72000000/71550000/71542100/71542068/88f9bf3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/72000000/71550000/71542100/71542068/ecd78162.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Brunswick Downtown Sugar Cube next to Bowdoin

[](https://www.expedia.com/Brunswick-Hotels-Brunswick-Downtown-Sugar-Cube-Next-To-Bowdoin.h71542068.Hotel-Information)

Brunswick

8.4/10

Very Good

(7 reviews)

"We ahd a great stay in Maine over the 4th visiting family, eating good food and walking around in great weather. Great stay in Brunswick, easy in and easy out and all sorts of things Maine accessible. Would recommend for anyone looking for a hassle-free weekend in coastal Maine. "

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

Tjorvi P.

$231 nightly

$252 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Brunswick-Hotels-Brunswick-Downtown-Sugar-Cube-Next-To-Bowdoin.h71542068.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/33000000/32840000/32833100/32833020/18ed00db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/33000000/32840000/32833100/32833020/338ff9c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/33000000/32840000/32833100/32833020/610158ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/33000000/32840000/32833100/32833020/108d7b71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Little Lincoln beautiful home

[](https://www.expedia.com/Boothbay-Harbor-Hotels-Little-Lincoln-Lovely-Home.h32833020.Hotel-Information)

Brunswick

9.0/10

Wonderful

(16 reviews)

"The host was very welcoming and responsive when we had a question. We would stay here again when we come back to Brunswick. "

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

Michael S.

$224 nightly

$244 total

Apr 12 - Apr 13

Total with taxes and fees

[](https://www.expedia.com/Boothbay-Harbor-Hotels-Little-Lincoln-Lovely-Home.h32833020.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91830000/91824000/91823998/cc7d4138.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/92000000/91830000/91824000/91823998/3e13b9b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/92000000/91830000/91824000/91823998/78dcd112.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/92000000/91830000/91824000/91823998/2736d12c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Full sized home

[](https://www.expedia.com/Harpswell-Hotels-Full-Sized-Home.h91823998.Hotel-Information)

Harpswell

9.8/10

Exceptional

(51 reviews)

"Super clean and lovely place to stay! Highly recommend!"

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

Evan B.

$336 nightly

$366 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Harpswell-Hotels-Full-Sized-Home.h91823998.Hotel-Information)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118710000/118703800/118703789/18f05291.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118710000/118703800/118703789/2db19464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118710000/118703800/118703789/ef7a7942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118710000/118703800/118703789/0ffa9ba1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Large, luxurious geodesic dome - 04

[](https://www.expedia.com/Freeport-Hotels-Large.h118703789.Hotel-Information)

Freeport

10/10

Exceptional

(2 reviews)

"We didn’t get enough time to evaluate but from the short visit, we can say that this is the small paradise within the Main area. Best camp ground facilities we have ever seen or experienced. Looking forward to visit with friends and extended families as well. "

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

Hrishi K.

$306 nightly

$334 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Freeport-Hotels-Large.h118703789.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/28000000/27480000/27476300/27476270/4847920a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/28000000/27480000/27476300/27476270/10493eba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/28000000/27480000/27476300/27476270/17224a0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27480000/27476300/27476270/d87ce049.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Centerview cottage

[](https://www.expedia.com/Harpswell-Hotels-Centerview-Cottage.h27476270.Hotel-Information)

Harpswell

9.6/10

Exceptional

(59 reviews)

"Great spot to relax and enjoy the beautiful outdoors. Very quiet and amazing views of the water. Everything needed for a comfortable and relaxing getaway. Highly recommend if coming to the area! "

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

Erin

$432 nightly

$471 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/Harpswell-Hotels-Centerview-Cottage.h27476270.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/104000000/103490000/103484100/103484082/w906h683x59y0-e2b546e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/104000000/103490000/103484100/103484082/w905h683x60y0-871ebbc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/104000000/103490000/103484100/103484082/w542h683x242y0-9ae4ee96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103490000/103484100/103484082/w907h683x58y0-58705ee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sweet comfy cottage on Small Point Road

[](https://www.expedia.com/Phippsburg-Hotels-Sweet-Comfy-Cottage-On-Small-Point-Road.h103484082.Hotel-Information)

Small Point

9.4/10

Exceptional

(3 reviews)

"Lovely home with plenty of space and seating. Not the most comfortable of beds but we enjoyed the space. Perfect location and would love to stay again. "

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

Liz J.

$508 nightly

$554 total

Mar 28 - Mar 29

Total with taxes and fees

[](https://www.expedia.com/Phippsburg-Hotels-Sweet-Comfy-Cottage-On-Small-Point-Road.h103484082.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/35000000/34430000/34429200/34429189/456eee4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34430000/34429200/34429189/031f8225.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34430000/34429200/34429189/5c9e0f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34430000/34429200/34429189/92b9303c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### City Amenities, Casco Bay Sunrises and Natural Beauty

[](https://www.expedia.com/Portland-Hotels-City-Amenities.h34429189.Hotel-Information)

East Deering

9.8/10

Exceptional

(127 reviews)

"Perfect location and the host was immediately repsonsive and always friendly!"

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

Jon L.

$235 nightly

$256 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Portland-Hotels-City-Amenities.h34429189.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/107000000/106380000/106377800/106377797/c0051374.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, internet, bed sheets](https://images.trvl-media.com/lodging/107000000/106380000/106377800/106377797/d66d7839.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106380000/106377800/106377797/7654ef7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/107000000/106380000/106377800/106377797/102a2deb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sunny Spot with Private Parking.

[](https://www.expedia.com/South-Portland-Hotels-Sunny-Spot-In-South-Portland-With-Private-Parking.h106377797.Hotel-Information)

Knightville

9.8/10

Exceptional

(25 reviews)

"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"

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

Giana

$167 nightly

$183 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/South-Portland-Hotels-Sunny-Spot-In-South-Portland-With-Private-Parking.h106377797.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/43000000/42540000/42537200/42537186/ab4230fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/43000000/42540000/42537200/42537186/6b48d324.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/43000000/42540000/42537200/42537186/02012889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/43000000/42540000/42537200/42537186/79f2e2db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Delightful 3BR Downtown Brunswick All King Beds

[](https://www.expedia.com/Boothbay-Harbor-Hotels-Beautiful-Delightful-3BR-Downtown-Brunswick-All-King-Beds.h42537186.Hotel-Information)

Brunswick

10/10

Exceptional

(22 reviews)

"Great place, super convenient to downtown."

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

Heather C.

$342 nightly

$373 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Boothbay-Harbor-Hotels-Beautiful-Delightful-3BR-Downtown-Brunswick-All-King-Beds.h42537186.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113680000/113674600/113674508/a67d235a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/114000000/113680000/113674600/113674508/f6a06df8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113680000/113674600/113674508/e5356195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113680000/113674600/113674508/687cf518.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful & minutes from the Old Port with private parking

[](https://www.expedia.com/South-Portland-Hotels-Peaceful-Minutes-From-The-Old-Port-With-Private-Parking.h113674508.Hotel-Information)

Knightville

9.6/10

Exceptional

(8 reviews)

"This well- appointed apartment was perfect for our stay in the Portland area. Jennifer was always quick to answer any questions. We would definitely recommend this listing."

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

Lynn E.

$225 nightly

$245 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/South-Portland-Hotels-Peaceful-Minutes-From-The-Old-Port-With-Private-Parking.h113674508.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=2026-04-10&endDate=2026-04-11&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=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&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=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&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=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=VACATION_HOME)

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=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=CONDO)

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=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=APART_HOTEL)

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=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&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=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=VILLA)

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## Top Bailey Island Hotel Reviews

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

### Portland Regency Hotel & Spa

10/10 Excellent

"Everything was great! "

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

![Hampton Inn Portland Downtown - Waterfront](https://images.trvl-media.com/lodging/5000000/4490000/4480300/4480291/bf7e40c4_y.jpg)

### Hampton Inn Portland Downtown - Waterfront

10/10 Excellent

"Great location, clean, very happy with our stay"

[](https://expedia.com/Portland-Hotels-Hampton-Inn-Portland-Downtown-Waterfront.h4480291.Hotel-Information)

![Clarion Hotel Portland Airport ME](https://images.trvl-media.com/lodging/1000000/10000/7200/7171/c90266f6_y.jpg)

### Clarion Hotel Portland Airport ME

10/10 Excellent

"Great rooms and nice staff"

[](https://expedia.com/Portland-Hotels-Clarion-Hotel-Portland.h7171.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

8/10 Good

"It was a smooth check in, friendly staff"

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

![Aloft Portland Downtown Waterfront ME](https://images.trvl-media.com/lodging/69000000/68850000/68847400/68847370/8a8afa7d_y.jpg)

### Aloft Portland Downtown Waterfront ME

10/10 Excellent

"This property is in a very convenient location for all that downtown Portland has to offer. "

[](https://expedia.com/Portland-Hotels-Aloft-Portland.h68847370.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

- Trending destinations on Expedia.com
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- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [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

### Can I find a vacation rental in Bailey Island?

### What are some of the best vacation rentals that Bailey Island has to offer?

### How many vacation rentals are there in Bailey Island?

### What can I see and do in Bailey Island?

### What are vacation rentals like in Bailey Island?

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- [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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