Bailey Island Treehouses, Townhouses & more


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Areas near Bailey Island

Great rentals within 20 miles that match your search

1 / 16

Beachfront Cottage on Indian Point

  • 2
  • 6
  • Min stay varies

$279

Details

1 / 30

The Tranquil Beauty

  • 3
  • 7
  • 7 nights min

$501

Details

1 / 24

The Coal Shack: Pet-Friendly Harborfront Studio in Downtown Boothbay

  • 2
  • Min stay varies

$140

Details

1 / 5

Colorful Sunny Second Floor

  • 1
  • 2
  • 4 nights min

$76

Details

1 / 12

The Gatehouse – B

  • 1
  • 2
  • Min stay varies

$155

Details

1 / 67

WILLARD BEACH with OCEAN VIEWS ~ 100 yds to beach!

  • 3
  • 9
  • Min stay varies

$295

Details

1 / 24

3BR Waterfront Home w/ Backyard Kayak Launch – 5 Mins to Botanical Gardens

  • 3
  • 6
  • 2 nights min

$248

Details

1 / 14

NEW! ‘Osprey Cottage’ 2BR South Freeport Cottage

  • 2
  • 6
  • Min stay varies

$250

Details

1 / 31

17B – Patio Home

  • 4
  • 8
  • Min stay varies

$205

Details

1 / 17

SOUTHPORT Waterfront Tidewater Farm with dock

  • 4
  • 6
  • 7 nights min

$357

Details

1 / 15

Beautiful 4BR House, Pool, Free Daily Breakfast

  • 4
  • 10
  • 4 nights min

$450

Details

1 / 156

Camp Card Cove

  • 4
  • 10
  • 7 nights min

$465

Details

1 / 12

Classic Maine Cottage with beautiful water views

  • 3
  • 8
  • Min stay varies

$145

Details

1 / 18

Beautiful views of the Open Ocean and Harbor

  • 4
  • 10
  • Min stay varies

$216

Details

1 / 73

WILLARD BEACH: Stunning newly RENOVATED HOUSE! 4 Mins to DT Portland.

  • 4
  • 17
  • Min stay varies

$546

Details

1 / 15

Quiet Lake Serenity Just 10 Miles from Portland

  • 3
  • 8
  • 7 nights min

$272

Details

1 / 42

Portland Area Cottage w/OCEAN VIEWS ~ pet friendly

  • 3
  • 6
  • Min stay varies

$295

Details

1 / 5

Sunny Home with Ocean Views

  • 3
  • 6
  • 3 nights min

$351

Details

1 / 23

220 Ft of Waterfront

  • 3
  • 10
  • Min stay varies

$229

Details

1 / 22

Casco Bay Atlantic Cape...POOL!

  • 4
  • 8
  • 1 night min

$176

Details

1 / 28

East End, Portland, - top neighborhood, near ocean and town

  • 3
  • 8
  • 3 nights min

$270

Details

1 / 20

Waterfront Cottage

  • 1
  • 2
  • 3 nights min

$174

Details

1 / 24

Romantic Crow’s Nest Hideaway with Deck and Treetop Vistas – Walk

  • 1
  • 2
  • Min stay varies

$103

Details

1 / 4

Oceanfront Cottage on Middle Bay

  • 3
  • 5
  • 7 nights min

$286

Details

1 / 14

True St Freeport

  • 2
  • 5
  • 2 nights min

$125

Details

1 / 8

Classic Harbor Cottage

  • 4
  • 5
  • Min stay varies

Inquire for Rates

Details

1 / 23

Spectacular Oceanfront Home w/ Private Cove, Dock

  • 6
  • 10
  • Min stay varies

$651

Details

1 / 13

6B – Officer’s Quarters

  • 4
  • 8
  • Min stay varies

$425

Details

1 / 12

Oceanfront Shingle Style

  • 6
  • 14
  • 7 nights min

$1001

Details

1 / 12

Hillcrest Cottage

  • 3
  • 6
  • Min stay varies

$341

Details

1 / 8

2 Bedroom Apartment at Moody Beach

  • 2
  • 5
  • 7 nights min

$171

Details

1 / 28

Sunrise Cottage

  • 4
  • 8
  • Min stay varies

$518

Details

1 / 27

2BR / 1B - Willard Beach -- South Portland

  • 2
  • 4
  • 3 nights min

$150

Details

1 / 19

Panoramic Ocean Views!

  • 2
  • 6
  • 7 nights min

$401

Details

1 / 22

Georgetown (Back River) Vacation Home

  • 5
  • 10
  • Min stay varies

$214

Details

1 / 14

Antique Cottage in Serene Setting

  • 2
  • 4
  • 7 nights min

$186

Details

1 / 28

Open Ocean Estate

  • 3
  • 10
  • 7 nights min

$526

Details

1 / 33

Historic Captain York House: 7 Bed, 6.5 Bath

  • 7
  • 14
  • Min stay varies

$401

Details

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