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Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Bailey Island vacation homes

Property grounds

Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
9.8 out of 10, Exceptional, (9 reviews)
"Orchid Harbor was perfect for my 3 week escape from life. Bailey Island is quiet and the house is comfortable and accommodating for family and friends.The outdoor seating along the ocean was our favorite place to be."
United States
Karen T.
The price is ￥33,897
￥73,728 total
includes taxes & fees
Apr 6 - Apr 7
Orchid Harbor, Bailey Island 3BR
TV

2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (3 reviews)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
The price is ￥14,918
￥31,886 total
includes taxes & fees
Mar 12 - Mar 13
2 bedroom w/ expansive water views
TV, fireplace, books

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

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
9.0 out of 10, Wonderful, (4 reviews)
"Good communication with host. Beautifully decorated. Well appointed kitchen and bath. Great wooded views. Quiet but close to restaurants and shopping."
United States
Lecia M.
The price is ￥10,439
￥41,709 total
includes taxes & fees
Mar 24 - Mar 25
1 Mi to Maine Street! MCM-Style Home in Brunswick
3 bedrooms, WiFi

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.8 out of 10, Exceptional, (16 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is ￥19,890
￥40,666 total
includes taxes & fees
Mar 12 - Mar 13
Fantastic Waterfront Views
TV

Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (5 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is ￥20,719
￥39,069 total
includes taxes & fees
Apr 5 - Apr 6
Mid Coast Getaway w/ water views
Interior

Modern Getaway by the Sea

Modern Getaway by the Sea
South Portland
10.0 out of 10, Exceptional, (2 reviews)
"Had a nice stay! House was great."
United States
Karen T.
The price is ￥47,358
￥79,855 total
includes taxes & fees
Mar 15 - Mar 16
Modern Getaway by the Sea
Exterior

Maine Luxury Home On the Sea

Maine Luxury Home On the Sea
Brunswick
Maine Luxury Home On the Sea
1 bedroom, internet, bed sheets

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
The price is ￥27,626
￥44,222 total
includes taxes & fees
Mar 16 - Mar 17
Charming 1-bedroom ADU in wonderful Portland neighborhood
Outdoor dining

Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (8 reviews)
"Such a beautiful home and peaceful location. We loved our stay and the host was responsive and helpful with any questions we had!"
United States
Diana H.
The price is ￥34,241
￥74,933 total
includes taxes & fees
Mar 13 - Mar 14
Mere Point Sunrise Views at Eastern Shore!
Exterior

New 2-bedroom townhouse close to Town, ocean, recreational, and Bowdoin College

New 2-bedroom townhouse close to Town, ocean, recreational, and Bowdoin College
Brunswick
The price is ￥23,363
￥38,027 total
includes taxes & fees
Apr 5 - Apr 6
New 2-bedroom townhouse close to Town, ocean, recreational, and Bowdoin College
Fridge, microwave, oven, stovetop

Award Winning Luxury Carriage House a short stroll from town!

Award Winning Luxury Carriage House a short stroll from town!
Bath
10.0 out of 10, Exceptional, (9 reviews)
"An exceptional property and guest. Would love to stay again next time Thank you Jared and Heather!"
United States
Ronald H.
The price is ￥67,091
￥102,553 total
includes taxes & fees
Mar 13 - Mar 14
Award Winning Luxury Carriage House a short stroll from town!
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (51 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
The price is ￥31,967
￥57,730 total
includes taxes & fees
Mar 16 - Mar 17
Full sized home
Interior

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very Good, (59 reviews)
"Nice place. Good location."
United States
Rob M.
The price is ￥22,211
￥47,783 total
includes taxes & fees
Mar 12 - Mar 13
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
TV, offices

Sleeps 16+ | W/D | Parking | 15 mins to Old Port

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
The price is ￥67,248
￥148,666 total
includes taxes & fees
Mar 12 - Mar 13
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Exterior detail

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (68 reviews)
"Had a really nice stay. "
United States
John F.
The price is ￥110,107
￥166,648 total
includes taxes & fees
Mar 16 - Mar 17
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Iron/ironing board, free WiFi, bed sheets

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

Spruce Studio: Near Beach+FirePit+Pond+Heat/AC+Fast WiFi
Georgetown
10.0 out of 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
Palmer M.
The price is ￥23,743
￥49,412 total
includes taxes & fees
Mar 25 - Mar 26
Spruce Studio: Near Beach+FirePit+Pond+Heat/AC+Fast WiFi
Terrace/patio

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is ￥33,151
￥55,750 total
includes taxes & fees
Mar 31 - Apr 1
Camp Forever cottage
Exterior

Willard Square Family Home

Willard Square Family Home
Willard Beach
9.6 out of 10, Exceptional, (9 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
The price is ￥38,676
￥83,537 total
includes taxes & fees
Mar 12 - Mar 13
Willard Square Family Home
Smart TV

Generous Living in a Warm, Welcoming Home

Generous Living in a Warm, Welcoming Home
Topsham
The price is ￥34,120
￥89,327 total
includes taxes & fees
Apr 5 - Apr 6
Generous Living in a Warm, Welcoming Home
Terrace/patio

Coastal Maine Retreat w/ Sprawling Ocean Views

Coastal Maine Retreat w/ Sprawling Ocean Views
West Point
8.6 out of 10, Excellent, (45 reviews)
"The property was perfect for our family get together. Close to different activities and food."
United States
Karen L.
The price is ￥24,863
￥48,566 total
includes taxes & fees
Apr 5 - Apr 6
Coastal Maine Retreat w/ Sprawling Ocean Views
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

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

4/10 Poor
"Breakfast doesn’t even start until 7. We had to leave before that. Many people stay for business and are gone by then. Also it was very cold and icy. The parking lot was pure ice and there was no salt or sand put down. We both almost landed on our faces and we had 2 children with us. "
Shawn 1-night trip
Posted 8 hours ago
Clarion Hotel Portland Airport ME

Find out more about Bailey Island

Bailey Island Vacation Homes information

Number of reviews
19,306
Accommodation
509 Vacation Homes
Lowest Price
￥11,723
Highest Price
￥23,255