Bailey Island Holiday House Rentals from AU$253: Search Holiday Homes

Bailey Island Holiday Homes
Maine
United States of America
Holiday Homes
Expedia.com.au

Bailey Island Travel Guide Hotels in Bailey Island Holiday Rentals in Bailey Island Bailey Island Car Hire Bailey Island Holiday Packages

A rocky shoreline with a boat, a house, and a forest in the background.

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Our top choices for Bailey Island holiday homes

A wooden deck with outdoor seating and string lights.

A kitchen with a dishwasher, a brick fireplace, and a dining area with a chandelier.

A cozy living room with a light blue sofa, patterned pillows, a glass coffee table, and a wooden chair.

A wooden staircase leading to a white door with a wreath and a flower pot on the steps.

1. Full sized home

Full sized home

Harpswell

9.8 out of 10, Exceptional, (69 reviews)

9.8/10

Exceptional

(69 reviews)

"The house was lovely and well kept and in a great location."

Angela M.

The price is AU$520

AU$520

includes taxes & fees

7 Oct - 8 Oct

Full sized home

A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

A bedroom with a bed, wooden ceiling, sliding glass doors to a balcony, a dresser, and a framed picture on the wall.

A cozy living room with a wooden ceiling, a beige sofa, a white coffee table, and a kitchen in the background.

A kitchen with wooden cabinets, a white refrigerator, a microwave, a stove, and a sign that reads "FRESH MAINE LOBSTERS".

2. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views

West Point

9.2 out of 10, Wonderful, (10 reviews)

9.2/10

Wonderful

(10 reviews)

"The location and views from the cottage are quintessential coastal Maine. Small community with lobster pound and Maine Oyster Company across the street. John is a welcoming host and eager to make sure you enjoy your stay. The cottage is great for 2 people, equipped with the basics and has a great deck to enjoy the views. Planning to return next year. Great spot!"

Rebecca

The price is AU$293

AU$293

includes taxes & fees

28 Sept - 29 Sept

Mid Coast Getaway w/ water views

A lakeside property with a deck, picnic table, and barbecue grill.

A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink. There is a table with magazines and a pair of scissors. A clock and a welcome sign are on the wall.

A metal staircase leading to a wooden deck over water, surrounded by greenery.

A compact living space with a kitchenette, a dining area with a table and chairs, a sofa, a ceiling fan, and a television.

3. Camp Forever cottage

Camp Forever cottage

Harpswell

9.6 out of 10, Exceptional, (68 reviews)

9.6/10

Exceptional

(68 reviews)

"Everything was great, fantastic location!"

Dennis H.

The price is AU$509

AU$509

includes taxes & fees

4 Oct - 5 Oct

Camp Forever cottage

A spacious room with a wooden floor, a dining area with chairs and a table, a sofa, a TV, and a balcony with a view of the sea.

A residential building with a wooden staircase leading to a second floor.

A bedroom with a bed, a desk, and a chair. There is a door leading to another room and a window with curtains.

A modern kitchen with granite countertops, a stainless steel range, and a wooden dining area with a view.

4. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views

West Point

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."

Gregory M.

The price is AU$360

AU$360

includes taxes & fees

29 Sept - 30 Sept

2 bedroom w/ expansive water views

A treehouse with a wooden staircase and a small building with a colorful mural.

A hallway with two rugs featuring anchor designs, white doors, and a ceiling light.

A silver convertible car parked in front of a red house with a garden.

A staircase with nautical-themed wall decorations.

5. Perfect stopover, getaway, base to explore the area, or to simply stay in town.

Perfect stopover, getaway, base to explore the area, or to simply stay in town.

Bath

8.0 out of 10, Very good, (30 reviews)

8.0/10

Very good

(30 reviews)

"A charming, quiet, and clean room with separate bathroom close to everything downtown. Felt a bit like staying at my grandparent’s house in a good way - it’s very homey. Dmitri is very nice and communication was thorough and easy!"

Esther

The price is AU$253

AU$253

includes taxes & fees

26 Sept - 27 Sept

Perfect stopover, getaway, base to explore the area, or to simply stay in town.

A spacious living room with large windows, a sofa, a chair, and a small table.

A spacious living area with a white sofa, a patterned rug, and a kitchen in the background.

A two-story house with a garage and a covered porch.

A covered outdoor seating area with three wooden chairs and a small table, surrounded by a stone wall and gravel ground.

6. 1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick

Brunswick

9.6 out of 10, Exceptional, (12 reviews)

9.6/10

Exceptional

(12 reviews)

"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "

Kendra G.

The price is AU$399

AU$399

includes taxes & fees

20 Oct - 21 Oct

1 Mi to Maine Street! MCM-Style Home in Brunswick

A spacious bedroom with a large bed, a rocking chair, and a view of a balcony with a white railing.

A spacious living room with a brick fireplace, a ceiling fan, and a large TV.

A neatly made bed with pillows and a blanket, a bedside lamp, and a small wooden nightstand with a lamp.

7. Fantastic Waterfront Views

Fantastic Waterfront Views

West Point

9.6 out of 10, Exceptional, (20 reviews)

9.6/10

Exceptional

(20 reviews)

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

Vanessa W.

The price is AU$305

AU$305

includes taxes & fees

28 Sept - 29 Sept

Fantastic Waterfront Views

A compact kitchen with a microwave, coffee maker, and a sink. There are cabinets, a dishwasher, and a dining table with chairs.

A shower area with a white tiled wall, a showerhead, and a curtain with a floral pattern.

A laundry room with a front-loading washer and dryer, wooden flooring, and a white door.

A dining area with a wooden table and chairs, a red sofa, and a small round table with a decorative plate.

8. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood

Freeport

The price is AU$560

AU$560

includes taxes & fees

26 Sept - 27 Sept

Quiet Spot in lovely Freeport neighborhood

A wooden deck with a view of a lake, surrounded by trees and shrubs.

A cabin room with a bed, a chair, a desk, and large windows with blinds.

A kitchen with wooden cabinets, a stove, a refrigerator, and a dining table with chairs.

A staircase with wooden steps and white walls, leading to an upper floor.

9. Centerview cottage

Centerview cottage

Harpswell

9.6 out of 10, Exceptional, (73 reviews)

9.6/10

Exceptional

(73 reviews)

"Incredible home in a beautiful location!"

Catherine G.

The price is AU$660

AU$660

includes taxes & fees

27 Sept - 28 Sept

Centerview cottage

A deck with white railings overlooking a body of water, boats, and a forested shoreline.

A kitchen with wooden cabinets, a large island with bar stools, a refrigerator, and a window with curtains.

A bedroom with a bed, two bedside lamps, a window with curtains, a framed picture on the wall, and a wooden nightstand.

A spacious kitchen with wooden cabinets, a dining area with chairs, and a staircase with wooden railings.

10. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape

West Point

The price is AU$309

AU$309

includes taxes & fees

28 Sept - 29 Sept

Captains Watch: A Coastal Escape

A wooden staircase with a wooden railing, surrounded by green foliage.

A bedroom with a navy blue bedspread, two matching pillows, a navy blue and white anchor-patterned rug, and two bedside tables with lamps.

A living room with a wooden chair, a blue patterned sofa, a television, and bookshelves.

A kitchen with a GE microwave, a coffee maker, and a kettle on the counter.

11. 1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!

1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!

Bath

8.2 out of 10, Very good, (21 reviews)

8.2/10

Very good

(21 reviews)

"Cute but aging small space, Near attractions"

michael

The price is AU$263

AU$263

includes taxes & fees

28 Sept - 29 Sept

1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!

A covered porch with a view of a lake and trees.

A house with a stone pathway leading to the front door, surrounded by lush greenery and a lake view.

A living room with a sofa, a coffee table, a television, and built-in shelving with books and decorative items.

A modern kitchen with wooden cabinets, stainless steel appliances, and a central island with bar stools.

12. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!

Brunswick

9.8 out of 10, Exceptional, (10 reviews)

9.8/10

Exceptional

(10 reviews)

"Lovely location "

Michelle S.

The price is AU$604

AU$604

includes taxes & fees

14 Oct - 15 Oct

Mere Point Sunrise Views at Eastern Shore!

A lush garden with a hammock, a variety of flowers, and a lake in the background.

A spacious living room with a sofa, two wicker chairs, a coffee table, and a fireplace.

A modern kitchen with a marble countertop, a gold faucet, and white cabinets. There is a painting on the wall and a chair in the background.

A dining table with a woven basket, a vase with flowers, and a framed picture on the wall.

13. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Classic New England Waterfront House Big Lawn Beautiful Sunrise

Harpswell

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"We had a wonderful stay! "

Ashma B.

The price is AU$2,502

AU$2,502

includes taxes & fees

12 Oct - 13 Oct

Classic New England Waterfront House Big Lawn Beautiful Sunrise

A room with a sliding glass door leading to an outdoor deck with Adirondack chairs and a table.

A room with large windows, a flat-screen TV, and a wooden floor.

A wooden staircase leading to a beach with a view of the ocean and distant land.

A spacious room with a large dining table, a comfortable seating area, and a television.

14. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport

Freeport

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

The price is AU$1,482

AU$1,482

includes taxes & fees

28 Sept - 29 Sept

Three bedroom in United States of America, Freeport

A rocking chair and a small table with a decorative plate, both placed on a wooden deck in front of a red building with a white door.

A cozy living room with a fireplace, two armchairs, a blue rug, and a window with blinds.

A bed with navy blue pillows featuring a ship and anchor design, a red and white houndstooth throw, and a view of trees through large windows.

15. 2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.

2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.

Bath

9.0 out of 10, Wonderful, (27 reviews)

9.0/10

Wonderful

(27 reviews)

"Clean, walkable to town, nice backyard to sit and talk."

Kathleen

The price is AU$340

AU$340

includes taxes & fees

28 Sept - 29 Sept

2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.

A cozy room with wooden flooring, wicker furniture, and a white brick wall.

A house with a front porch, a small patio, and a fenced backyard.

A dining area with a wooden table set for four, surrounded by wicker chairs.

A kitchen with wooden cabinets, a built-in oven, a microwave, and a refrigerator.

16. Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

Brunswick

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"Great location"

Ashley W.

The price is AU$1,046

AU$1,046

includes taxes & fees

28 Sept - 29 Sept

Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

A bedroom with a bed, a small table with a yellow mug, and a window with a view of a forest.

A small, dark-colored cabin with a single window and a door, surrounded by a forested area.

A cozy room with a built-in bench, a round window, and a bookshelf.

A cabin with a large glass door, wooden deck, and string lights.

17. Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

Georgetown

10.0 out of 10, Exceptional, (2 reviews)

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!"

Palmer M.

The price is AU$566

AU$566

includes taxes & fees

18 Oct - 19 Oct

Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

A modern kitchen with a large island, dark cabinetry, and a view of a lake.

A well-maintained garden with a variety of plants and flowers, a large rock in the foreground, and a lake in the background.

A wooden deck with two wicker chairs and a glass table, overlooking a lake and surrounded by trees.

18. The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury

The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury

Harpswell

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Beautiful property, well equipped, lots of amenities, plenty of space for our large group."

Edwin M.

The price is AU$3,243

AU$3,243

includes taxes & fees

5 Oct - 6 Oct

The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury

A hallway with a large, rustic mirror leaning against the wall, a potted plant in the foreground, and a glimpse of a bed with a yellow blanket in the background.

A kitchen with white cabinets, a dining table with a black chair, a framed picture on the wall, and a lamp on the table.

A living room with a sectional sofa, a coffee table, and a rug. There are two framed pictures on the wall and a lamp on a side table.

A two-story house with a front porch, surrounded by a well-maintained lawn and trees.

19. Lush Coastal Downtown Home - Beaches & Shopping

Lush Coastal Downtown Home - Beaches & Shopping

Freeport

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"Our stay was very comfortable and easy to navigate. The host was very communicative. We had everything we needed and more. It was nice to be in walking distance from downtown Freeport. Although the price was higher than we wanted, our family of four (2 teens) enjoyed having a clean, comfortable and seamless stay."

Alana K.

The price is AU$863

AU$863

includes taxes & fees

26 Sept - 27 Sept

Lush Coastal Downtown Home - Beaches & Shopping

A two-story white house with a front porch, green shutters, and a covered patio area with chairs.

A two-story white house with a porch and a lawn with fallen leaves.

A modern kitchen with white cabinets, stainless steel appliances, and a dark countertop.

A white house with a covered porch, a brick pathway, and a white picket fence.

20. Charming Historic home steps away from downtown

Charming Historic home steps away from downtown

Bath

9.0 out of 10, Wonderful, (2 reviews)

9.0/10

Wonderful

(2 reviews)

"The communication was excellent. The location was excellent."

Holly Y.

The price is AU$1,029

AU$1,029

includes taxes & fees

6 Oct - 7 Oct

Charming Historic home steps away from downtown

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.

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