Bailey Island Holiday Houses

Bailey Island Holiday Homes
Maine
United States of America
Holiday Homes
Expedia.co.nz

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

A sliding glass door leading to a room with a wooden floor and a bed.

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

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 NZ$638

NZ$638

includes taxes & fees

5 Oct - 6 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 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".

A cozy living room with a sofa, chairs, a dining table, and a kitchen area with wooden cabinets and a refrigerator.

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 NZ$358

NZ$358

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

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.

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 NZ$634

NZ$634

includes taxes & fees

3 Oct - 4 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 spacious living room with a large sofa, wooden flooring, and a ceiling fan.

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 NZ$442

NZ$442

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 neatly arranged bedroom with a patterned bedspread, a desk, and a chair.

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 NZ$310

NZ$310

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 NZ$480

NZ$480

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 dining area with a long wooden table and chairs, a spiral staircase, and a large window providing a view of the outdoors.

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

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 NZ$372

NZ$372

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 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.

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

8. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood

Freeport

The price is NZ$707

NZ$707

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 living room with a sofa, a green couch, a coffee table, a fireplace, and a staircase.

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

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 NZ$835

NZ$835

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 dining area with a wooden table and chairs, a staircase, and a view of the outdoors.

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

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

10. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape

West Point

The price is NZ$377

NZ$377

includes taxes & fees

28 Sept - 29 Sept

Captains Watch: A Coastal Escape

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

A porch with a rocking chair and a metal bench with decorative plates.

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.

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 NZ$323

NZ$323

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 stone pathway leading to a building with a wooden fence on one side.

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

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

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 NZ$765

NZ$765

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

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

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

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 NZ$3,095

NZ$3,095

includes taxes & fees

19 Oct - 20 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 wooden staircase leading to a beach with a view of the ocean and distant land.

A coastal property with multiple houses, a stone retaining wall, and a wooden staircase leading to the houses.

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

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 NZ$1,903

NZ$1,903

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 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.

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

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

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 NZ$415

NZ$415

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 modern kitchen with wooden cabinets, a granite countertop, a coffee maker, and a dishwasher.

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

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

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 NZ$1,273

NZ$1,273

includes taxes & fees

5 Oct - 6 Oct

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 beach with a sandy shore, waves, and a forested hill in the background.

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

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

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 NZ$695

NZ$695

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

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

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 NZ$4,016

NZ$4,016

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 bedroom with a bed, pillows, a bedside table with a lamp, a framed picture, and a window with a view of greenery.

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

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

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 NZ$1,067

NZ$1,067

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

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

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 NZ$1,303

NZ$1,303

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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Top Bailey Island Hotel Reviews

Cambria Hotel Portland Downtown-Old Port

10/10 Excellent

"."

Jessica 1-night trip

Posted 1 hour ago

Cambria Hotel Portland Downtown-Old Port

Portland Regency Hotel & Spa

10/10 Excellent

"Hotel was very nice and clean rooms updated and hotel staff friendly and helpful. I recommend if staying in old port area. Valet is $40 a night as parking options are limited downtown but other than that a very nice hotel."

Elizabeth 1-night trip

Posted 2 hours ago

Portland Regency Hotel & Spa

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

8/10 Good

"Simple operation. Good ice machine."

Marc 4-night trip

Posted 8 hours ago

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

10/10 Excellent

"Breakfast was sparse and wasn’t replenished in the last hour or so of breakfast service."

LINDA 1-night trip

Posted 9 hours ago

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

Clarion Pointe South Portland

8/10 Good

"Staff was helpful, beds comfortable and"

Linda 4-night trip

Posted 1 day ago

Clarion Pointe South Portland

Embassy Suites by Hilton Portland Maine

10/10 Excellent

"I’ve stayed there previously and it’s always a good stop a good spot to get to the airport and friendly staff"

gemma 1-night trip

Posted 1 day ago

Embassy Suites by Hilton Portland Maine

Hampton Inn Portland Downtown - Waterfront

10/10 Excellent

"Great location. Staff and hotel were great"

Amy 1-night trip

Posted 1 day ago

Hampton Inn Portland Downtown - Waterfront

The Westin Portland Harborview

10/10 Excellent

"Very professional staffed Great amenities."

Richard 1-night trip

Posted 3 days ago

The Westin Portland Harborview

Find out more about Bailey Island

Bailey Island Holiday Homes information

Number of reviews	365
Accommodation	614 Holiday Homes
Lowest Price	NZ$310
Highest Price	NZ$4,016

Explore a world of travel with Expedia

More ways to book

Book Holiday Homes in Bailey Island on Expedia.com

Holiday Homes in Bailey Island

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Bailey Island holiday homes

1. Full sized home

2. Mid Coast Getaway w/ water views

3. Camp Forever cottage

4. 2 bedroom w/ expansive water views

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

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

7. Fantastic Waterfront Views

8. Quiet Spot in lovely Freeport neighborhood

9. Centerview cottage

10. Captains Watch: A Coastal Escape

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

12. Mere Point Sunrise Views at Eastern Shore!

13. Classic New England Waterfront House Big Lawn Beautiful Sunrise

14. Three bedroom in United States of America, Freeport

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

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

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

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

19. Lush Coastal Downtown Home - Beaches & Shopping

20. Charming Historic home steps away from downtown

Find holiday rentals that suit your style

Top Bailey Island Hotel Reviews

Cambria Hotel Portland Downtown-Old Port

Find out more about Bailey Island

Bailey Island Holiday Homes information

Explore a world of travel with Expedia