Search Vacation Homes in Bailey Island

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Nov 14 - Nov 16
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Nov 21 - Nov 23
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Dec 5 - Dec 7
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Jan 2 - Jan 4

Vacation Homes in Bailey Island

Beach
Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR

Harpswell
9.8 out of 10, Exceptional, (7)
"We enjoyed our weekend tremendously, especially being right on the beach, with miles of private access to the rocky shores to search for treasures and sea glass! Thank you so much!"
United States
Jason M.
$411 nightly
The price is $415
Nov 24 - Nov 25
Total with taxes and fees
Orchid Harbor, Bailey Island 3BR
Hair dryer, towels, soap, toilet paper
Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood

Back Cove
$214 nightly
The price is $233
Nov 10 - Nov 11
Total with taxes and fees
Charming 1-bedroom ADU in wonderful Portland neighborhood
Property grounds
Captain's Guest Room w/private bath. Walk to everything.

Captain's Guest Room w/private bath. Walk to everything.

Bath
8.2 out of 10, Very Good, (21)
"Clean, well maintained, slighly funky in an historical way . Very convenient to great breakfast spots and downtown Bath. Would stay there again."
United States
Benjamin E.
$146 nightly
The price is $159
Nov 10 - Nov 11
Total with taxes and fees
Captain's Guest Room w/private bath. Walk to everything.
Dining
Escape to Positive Outlook

Escape to Positive Outlook

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.
$205 nightly
The price is $217
Dec 1 - Dec 2
Total with taxes and fees
Escape to Positive Outlook
Property grounds
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome

Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome

Boothbay
9.0 out of 10, Wonderful, (68)
"The house was so charming, clean, and comfortable. We couldn’t have found a better place to stay during our visit to the Boothbay area. The Dome House is off the beaten track, right on a tidal river, which made every day and every hour a new private view. Be sure to schedule time to simply be. This is the perfect house for it!"
United States
Lawton S.
$284 nightly
The price is $310
Nov 11 - Nov 12
Total with taxes and fees
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome
Exterior
Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!

Brunswick
9.8 out of 10, Exceptional, (7)
"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.
$374 nightly
The price is $378
Nov 12 - Nov 13
Total with taxes and fees
Mere Point Sunrise Views at Eastern Shore!
Fridge, microwave, stovetop, coffee/tea maker
The Outlet Studio, Rustic Comfort w Fireplace

The Outlet Studio, Rustic Comfort w Fireplace

Freeport
10.0 out of 10, Exceptional, (11)
"Very comfortable and homey Great location to the outlets. "
United States
Patricia C.
$151 nightly
The price is $164
Nov 10 - Nov 11
Total with taxes and fees
The Outlet Studio, Rustic Comfort w Fireplace
Interior
Captain's Quarters 1BR Guest Suite. Quiet. Walk to everything.

Captain's Quarters 1BR Guest Suite. Quiet. Walk to everything.

Bath
7.6 out of 10, Good, (12)
"Very nice cozy place to make home base for a week. Had everything I needed and owner was very responsive with all of my questions. Primary destination was Bath and very convenient to everything I needed. Thank you!"
United States
Carol N.
$145 nightly
The price is $158
Nov 10 - Nov 11
Total with taxes and fees
Captain's Quarters 1BR Guest Suite. Quiet. Walk to everything.
TV
Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views

West Point
9.0 out of 10, Wonderful, (4)
"Seeing the water from the living room and porch was spectacular -- we watched the fishing boats come and go and a pair of bald eagles fishing. Loved all the natural light! "
United States
Wendy L.
$179 nightly
The price is $188
Nov 10 - Nov 11
Total with taxes and fees
Mid Coast Getaway w/ water views
3 bedrooms, WiFi
Fantastic Waterfront Views

Fantastic Waterfront Views

West Point
9.8 out of 10, Exceptional, (12)
"The place is amazing with lots of room for a family, and great views of the water from almost everywhere. The neighborhood is quiet and the people were very friendly. "
United States
Joseph V.
$255 nightly
The price is $269
Nov 30 - Dec 1
Total with taxes and fees
Fantastic Waterfront Views
Fridge, microwave, oven, stovetop
Beautiful 3BR Home with Office in Town of Brunswick with King beds

Beautiful 3BR Home with Office in Town of Brunswick with King beds

Brunswick
9.2 out of 10, Wonderful, (5)
"Great place for our family to stay while visiting the Maine coast."
United States
Craig C.
$322 nightly
The price is $351
Nov 12 - Nov 13
Total with taxes and fees
Beautiful 3BR Home with Office in Town of Brunswick with King beds
Property grounds
Centerview cottage

Centerview cottage

Harpswell
9.6 out of 10, Exceptional, (59)
"Had a great stay at the Centerview cottage! Views were spectacular, saw lots of wildlife right from the deck. We enjoyed paddling around the area with the kayaks and jumping in for a quick dunk from the dock. Can’t wait to come back next summer."
United States
Jennifer O.
$345 nightly
The price is $376
Dec 1 - Dec 2
Total with taxes and fees
Centerview cottage
Fridge, microwave, oven, stovetop
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Brunswick
8.8 out of 10, Excellent, (21)
"Great location for baileys island and popham"
United States
Anonymous traveler
$367 nightly
The price is $400
Nov 16 - Nov 17
Total with taxes and fees
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Private kitchen
Spacious Portland Home + Parking

Spacious Portland Home + Parking

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.
$532 nightly
The price is $580
Nov 10 - Nov 11
Total with taxes and fees
Spacious Portland Home + Parking
Outdoor dining
Camp Forever cottage

Camp Forever cottage

Harpswell
9.6 out of 10, Exceptional, (57)
"Nice, quiet location. Bed is super comfortable, and everything is neat and clean inside. We were a little confused which kayaks we could use and how to get them down to the water, and we were encouraged to use life vests, but there were none available (and we did not bring any with us). Otherwise, hosts were very responsive and we had a nice time."
United States
Lisa K.
$355 nightly
The price is $387
Nov 30 - Dec 1
Total with taxes and fees
Camp Forever cottage
Terrace/patio
Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!

Munjoy Hill
10.0 out of 10, Exceptional, (34)
"Adorable and pristine place, with many thoughtful amenities. Great location. Incredible host. Loved our stay."
United States
Brant H.
$308 nightly
The price is $336
Nov 10 - Nov 11
Total with taxes and fees
Modern & Sunny House Steps from the Promenade. Private Parking!
Property grounds
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

West End
8.6 out of 10, Excellent, (56)
"Quiet, close to everything and east to find."
United States
Jesse M.
$291 nightly
The price is $317
Nov 10 - Nov 11
Total with taxes and fees
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Private kitchen
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

Cash Corner
$579 nightly
The price is $631
Dec 8 - Dec 9
Total with taxes and fees
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
Private kitchen
Classic New England Waterfront

Classic New England Waterfront

Harpswell
10.0 out of 10, Exceptional, (2)
"We had a wonderful stay! "
United States
Ashma B.
$651 nightly
The price is $710
Dec 1 - Dec 2
Total with taxes and fees
Classic New England Waterfront
Interior
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Scarborough
10.0 out of 10, Exceptional, (7)
"We loved our weekend getaway! The back yard set up was amazing and perfect for our rainy Saturday!"
United States
Alicia D.
$527 nightly
The price is $574
Nov 11 - Nov 12
Total with taxes and fees
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
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

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

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

10/10 Excellent
"Very clean hotel"
Marijana 2-night trip
Posted 1 hour ago
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Find out more about Bailey Island

Bailey Island Vacation Homes information

Number of reviews
335
Accommodation
524 Vacation Homes
Lowest Price
$158
Highest Price
$710

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