Search Vacation Homes in Bailey Island

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Vacation Homes in Bailey Island

Dining
Escape to Positive Outlook

Vacation Home in West Point

10.0 out of 10, Exceptional, (2)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
The price is SAR 355
SAR 758 total
includes taxes & fees
9 Dec - 10 Dec
Escape to Positive Outlook
Fridge, microwave, stovetop, coffee/tea maker
The Outlet Studio, Rustic Comfort w Fireplace

Vacation Home in Freeport

10.0 out of 10, Exceptional, (11)
"Very comfortable, clean, with a spacious bathroom and within walking distance of downtown Freeport and Bow Street Market"
United States
Deanna S.
The price is SAR 304
SAR 597 total
includes taxes & fees
9 Dec - 10 Dec
The Outlet Studio, Rustic Comfort w Fireplace
Fridge, microwave, oven, stovetop
Beautiful 3BR Home with Office in Town of Brunswick with King beds

Vacation Home in Brunswick

9.2 out of 10, Wonderful, (5)
"Great place for our family to stay while visiting the Maine coast."
United States
Craig C.
The price is SAR 525
SAR 1,334 total
includes taxes & fees
21 Dec - 22 Dec
Beautiful 3BR Home with Office in Town of Brunswick with King beds
3 bedrooms, WiFi
Fantastic Waterfront Views

Vacation Home in West Point

9.6 out of 10, Exceptional, (14)
"Our favorite part about our stay at this location was being able to look out the many sliding door windows to see the ocean view. It was a very relaxing place to stay. "
United States
Heather S.
The price is SAR 788
SAR 1,398 total
includes taxes & fees
5 Jan - 6 January 2026
Fantastic Waterfront Views
Fridge, microwave, oven, stovetop
Huge Historic Downtown Townhome

Vacation Home in West End

9.8 out of 10, Exceptional, (8)
"The house is so charming and in an excellent location! It is walking distance to many options, on a quiet, beautiful street with comfortable beds and a well appointed kitchen. Easy booking and communication throughout! "
United States
Siobhain C.
The price is SAR 446
SAR 1,447 total
includes taxes & fees
9 Dec - 10 Dec
Huge Historic Downtown Townhome
Fridge, microwave, oven, stovetop
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Vacation Home in Brunswick

8.8 out of 10, Excellent, (23)
"Nice place, I'd stay again!"
United States
Ronnie C.
The price is SAR 544
SAR 1,465 total
includes taxes & fees
21 Dec - 22 Dec
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Private kitchen
Spacious Portland Home + Parking

Vacation Home in Parkside

9.0 out of 10, Wonderful, (2)
"we used the house has home base for several outings in Portland. Great location and easy parking."
United States
Ellen M.
The price is SAR 619
SAR 2,176 total
includes taxes & fees
9 Dec - 10 Dec
Spacious Portland Home + Parking
Outdoor dining
Camp Forever cottage

Vacation Home in Harpswell

9.6 out of 10, Exceptional, (58)
"Most enjoyed vacation this year.Location was beautiful. "
United States
Debra S.
The price is SAR 788
SAR 1,362 total
includes taxes & fees
31 Dec - 1 January 2026
Camp Forever cottage
Terrace/patio
Modern & Sunny House Steps from the Promenade. Private Parking!

Vacation Home in Munjoy Hill

10.0 out of 10, Exceptional, (37)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is SAR 597
SAR 1,239 total
includes taxes & fees
9 Dec - 10 Dec
Modern & Sunny House Steps from the Promenade. Private Parking!
Interior
Spacious Country Home Freeport, Only 5 min to LL Bean!

Vacation Home in Freeport

9.6 out of 10, Exceptional, (15)
"It was a very relaxing house to stay in. Everything was provided in the kitchen, bathroom and bedrooms. Lots of room for all of us to mingle. "
United States
Carla S.
The price is SAR 559
SAR 1,748 total
includes taxes & fees
9 Dec - 10 Dec
Spacious Country Home Freeport, Only 5 min to LL Bean!
Fridge, microwave, oven, stovetop
Modern Getaway by the Sea

Vacation Home in South Portland

10.0 out of 10, Exceptional, (2)
"Had a nice stay! House was great."
United States
Karen T.
The price is SAR 938
SAR 1,682 total
includes taxes & fees
8 Jan - 9 January 2026
Modern Getaway by the Sea
Private kitchen
Classic New England Waterfront

Vacation Home in Harpswell

10.0 out of 10, Exceptional, (2)
"Great property"
United States
Scott D.
Classic New England Waterfront
Fridge, microwave, oven, stovetop
Generous Living in a Warm, Welcoming Home

Vacation Home in Topsham

The price is SAR 558
SAR 1,825 total
includes taxes & fees
9 Dec - 10 Dec
Generous Living in a Warm, Welcoming Home
Paper towels
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

Vacation Home in Brunswick

2.0 star property
The price is SAR 619
SAR 1,669 total
includes taxes & fees
21 Dec - 22 Dec
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
1 bedroom, internet, bed sheets
Charming 1-bedroom ADU in wonderful Portland neighborhood

Vacation Home in Back Cove

Charming 1-bedroom ADU in wonderful Portland neighborhood
Fridge, microwave, oven, stovetop
Maine Luxury Home On the Sea

Vacation Home in Brunswick

The price is SAR 992
SAR 2,873 total
includes taxes & fees
9 Dec - 10 Dec
Maine Luxury Home On the Sea
Fridge, microwave, oven, stovetop
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

Vacation Home in Freeport

10.0 out of 10, Exceptional, (4)
"We had a wonderful time in Freeport, getting some Christmas season shopping in and bring our 4 year old to the Sparkle weekend festivities. "
United States
David H.
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Smart TV, books
Ambleside in Boothbay Harbor Maine! Perfect for a warm and cozy Gardens Aglow!

Vacation Home in Boothbay Harbor

10.0 out of 10, Exceptional, (7)
"The property is beautiful and within walking distance to the main town area. The house has plenty of space for my family of 10 and the host went above and beyond with amenities."
United States
Leang C.
The price is SAR 2,440
SAR 3,273 total
includes taxes & fees
9 Dec - 10 Dec
Ambleside in Boothbay Harbor Maine! Perfect for a warm and cozy Gardens Aglow!
Property grounds
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

Vacation Home in West End

8.4 out of 10, Very Good, (58)
"Quiet, close to everything and east to find."
United States
Jesse M.
The price is SAR 560
SAR 1,175 total
includes taxes & fees
14 Dec - 15 Dec
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Fridge, microwave, oven, stovetop
Award Winning Luxury Carriage House a short stroll from town!

Vacation Home in Bath

2.0 star property
10.0 out of 10, Exceptional, (9)
"An exceptional property and guest. Would love to stay again next time Thank you Jared and Heather!"
United States
Ronald H.
The price is SAR 1,595
SAR 2,430 total
includes taxes & fees
10 Dec - 11 Dec
Award Winning Luxury Carriage House a short stroll from town!
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

Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

10/10 Excellent
"The staff was very pleasant and helpful. The room was clean. "
Deborah 1-night trip
Posted 2 days ago
Comfort Inn South Portland Airport