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Winslow Rentals

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Winslow Rentals

1,061 Houses

TARBOX COTTAGE | WESTPORT ISLAND | HISTORICAL FARM HOUSE | 600ft OF WATERFRONT |

Wiscasset house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$293

1 / 29

Evergreen Hill

Southwest Harbor house

3 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$400

1 / 21

Perfect for Two...Historic cottage with harbor views and waterfront access

Port Clyde house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$150

1 / 17

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

Boothbay Harbor apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$116

1 / 25

Mazu, the Bed&Boat, the most waterfront cottage

Damariscotta yacht

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$225

1 / 19

The Maine Hideaway - Pilot House Room

Brooklin b and b

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$165

1 / 9

M&M Cottage - Walk to Town from this Roomy Boothbay Harbor House, Pet Friendly

Boothbay Harbor house

2 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$140

1 / 33

Peaceful Lakeside Cabin on Shores of Biscay

Bremen log cabin

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$125

1 / 16

Midcoast Guest House on farm w/2 kayaks, close to ocean

Cushing guest house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$125

1 / 18

Mavooshen Retreat at Sprucewold, Private Beach Access, Minutes to Downtown

Boothbay Harbor log cabin

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$170

1 / 29

Campabella - rustic beauty on Isle au Haut

Isle Au Haut log cabin

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$123

1 / 15

The Pickering House - an 1854 Harbor View Home

Deer Isle farmhouse

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 26 minutes

Price per night from

$314

1 / 26

The Community House on Rockport Harbor with dock

Rockport house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 58 minutes

Price per night from

$145

1 / 34

Oceanfront 2BR Cottage on Wooded Half Acre w/ Ocean View

East Boothbay cottage

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$141

1 / 26

The Loft Guest Cottage

New Harbor house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 14 minutes

Price per night from

$171

1 / 12

Quintessential Maine! Green Gables Oceanfront 4BR Cottage w/ Private Beach

Friendship house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$243

1 / 31

Secluded 3BR Home w/ Beautiful Water Views

Boothbay house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$159

1 / 24

Oceanside cottage with private dock - newly updated and private

Rockland house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$160

1 / 14

Maine. Lovely Cottage on Penobscot Bay

Penobscot cottage

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$154

1 / 20

Condo on Grand Beach(OOB)-Steps to Beach, Pool

Old Orchard Beach condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 46 minutes

Price per night from

$207

1 / 10

Quarterdeck 2 bedroom shore front fabulous sunsets

Trenton cottage

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$214

1 / 9

DOCS PLACE ON SOUTHPORT ISLAND | CAPE NEWAGEN | STONE FIREPLACE | PRIVATE DOCK &

Southport house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$419

1 / 13

Couples cottage at the head of Mackerel Cove with views to Mt. Washington.

Orrs Island cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$140

1 / 22

Oceanfront Log Cabin, 1BR Haven w/ Loft, Sunroom, Swim Inlet & Stunning Views

Squirrel Island log cabin

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$150

1 / 24

Family Friendly Cottage on Androscoggin Lake

Leeds cottage

2 bedrooms / 1 bathroom / sleeps 7

Price per night from

$250

1 / 6

Charming water view home overlooking Mill Cove w/ a large deck - near town

Boothbay Harbor house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 34 minutes

Price per night from

$74

1 / 29

Spectacular Ocean Views & Private Beach, Minutes from Popham & Sebasco Resort

Phippsburg house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$197

1 / 29

Sensational 5* Apt. in 1862 Sea Captain's House

Rockland apartment

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 49 minutes

Price per night from

$195

1 / 14

Brand new cottage with a screened porch & woodland views - close to Acadia!

Bar Harbor house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 34 minutes

Price per night from

$113

1 / 24

Caretakers Cottage

Camden house

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$350

1 / 13

Long Cove Cottages

Tenants Harbor cottage

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$114

1 / 29

Price per night from

$325

1 / 16

Charming home w/ ocean views, large deck, entertainment - walk to beach!

Trevett house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 1 hour 34 minutes

Price per night from

$130

1 / 31

Estabrooke Cottage, in the Heart of the Village of Castine

Castine house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$142

1 / 10

Home & Cottage w/ Great Ocean Views near Acadia

Tremont house

7 bedrooms / 5 bathrooms / sleeps 16

Responds fast! avg. 1 hour 34 minutes

Price per night from

$586

1 / 44

Pine Point Beach Studio condo

Scarborough condo

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$75

1 / 24

The Barn

Alna house

3 bedrooms / 2 bathrooms / sleeps 12

Responds fast! avg. 3 hours 13 minutes

Price per night from

$300

1 / 20

Back Bay Cottage - Portside: Luxury Condo on Water

Boothbay Harbor apartment

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 10 minutes

Price per night from

$284

1 / 12
Viewing 38 of 1,061
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