Vacation Rentals & Cabins in Winthrop

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71 Houses

Waterfront Cottage, Stroll Away from Historic Bath

Bath cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Waterfront Car not required

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Price per night from

$320

Oceanfront Cottage On Linekin Bay Boothbay Harbor

Boothbay Harbor cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$287

Tiny House Cottage

Boothbay Harbor house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$172

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SUMMER COTTAGE BY THE SEA

Swans Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Car not required, Waterfront

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Price per night from

$287

Chadwick House

Friendship house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Car not required, Waterfront

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Price per night from

$459

Waterfront Cottage on Mount Desert Isle - 8 Mi from Acadia

Mount Desert cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Car not required, Waterfront

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Price per night from

$717

Private Island - Great for Reunions - Sleeps 24

Port Clyde house

  • 11 bedrooms
  • 6 bathrooms
  • sleeps 24

1 of 2 match: Car not required, Waterfront

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Price per night from

$2,458

West Lee Cottage

Swans Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 46 minutes

1 of 2 match: Car not required, Waterfront

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Price per night from

$184

Virginia's Sunset at Sunset Cottages

Bernard cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Car not required, Waterfront

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Price per night from

$153

Cedarledge Cottage at Seaside Cottages, waterfront, Acadia - "quiet" side of MDI

Southwest Harbor cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Car not required, Waterfront

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Price per night from

$263

Maine Ocean Front 2 Bedroom Cottage

Tenants Harbor cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“A Little Bit of Heaven” Several years ago I had the good fortune to rent this cottage "sight unseen" and have been returning each year for 10 or so years which tells you how much I love it here. Dream about it in the winter too. It is immaculate, close to a small beach, stores, and not too far from Rockland and Camden. If I could, I would spend the summer here and be in heaven! Tranquil, beautiful, soothing and good for the soul are some of the ways I would describe Hupper Cottage. The owners are terrific and most accommodating. In my opinion you won't find a better place to stay in Maine for rest and relaxation! Walking and sight seeing are great, and the lobster and sunsets are fabulous! Great hub for sightseeing in mid-coast Maine as well.

Responds fast! avg. 2 hours 24 minutes

1 of 2 match: Car not required, Waterfront

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Price per night from

$161

Pauls Cottage @ Seaside Cottages, Mt Desert Acadia

Southwest Harbor cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Car not required, Waterfront

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Price per night from

$394

Oar Island

Bremen cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

“perfect” We love Oar Island. It is the perfect vacation place for families with children of different ages, or just a couple. There is hiking, sunning, relaxation, but mostly what we love about Oar Island is the isolation. It is an adventure as well, since the only way to get there is by the little motorboat. It is a getaway for certain kinds of people; but if you prefer the Marriott type of stay, this is not that kind, it is much more "out-doorsy".

1 of 2 match: Car not required, Waterfront

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Price per night from

$270

Waterfront villa, Coastal Southern Maine

Scarborough house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 10

1 of 2 match: Car not required, Waterfront

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Price per night from

$1,148

Annie's Outlook at Sunset Cottages

Acadia National Park cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Great location, beautiful view, cosy place” We visited for a week with our kids (9, 12 years) in July, I can only support my Co-reviewers: a most beautiful location, the sea at your feet, a spectacular sight with sunsets and rocks for kids to climb, with love, taste and insight prepared surroundings (find a bench/picknic table at the places you like to sit), a cosy, clean place, with all you need to feel comfortable, kind people meeting your needs/wishes whereever possible, lots of interesting things to do (hikes, biking, whale watching) in close distance.

1 of 2 match: Car not required, Waterfront

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Price per night from

$186

Pinelodge Cottage, Quiet side of Mt. Desert Island, Acadia Natl.Park, waterfront

Mount Desert cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Car not required, Waterfront

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Price per night from

$279

The Gray Barn

Bass Harbor apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Close to Nirvana” It would be difficult to find a better spot for spending a vacation than the Quietside of Mt. Desert, and the Gray Barn experience is part of the fun. The accomodations are modern and in great shape, and the windows both have a great view over upper Bass Harbor and give great air circulation. Access to cellphone and internet coverage is a convenience. The kitchen is very functional, though you'll want to visit the lobster pounds and restaurants in the area. A perfect base for hiking in acadia National Park. The week we were there was perfect for using the owner's kayaks in the upper harbor and the estuary beyond. We've stayed three different years and will be happy to return.

1 of 2 match: Car not required, Waterfront

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Price per night from

$229

Grace Cottage

Long Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Car not required, Waterfront

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Price per night from

$413

Little Cottage at Sunset Cottages

Bernard cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Peaceful, Romantic and Inspiring” First I must say that all folks involved in the rental and care of the cottages are the tops. They know just how to be there for everything you might need without being intrusive, and the cottage is very bright and clean. This small cottage is on one spectacular piece of property where we sat by the cove each night in strategically placed adirondack chairs to watch the glorious sunsets. Cannot recommend Little Cottage too highly for a couple or single, as long as they are not too tall. The location is perfect for those who want to be on the quiet side.

1 of 2 match: Car not required, Waterfront

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Price per night from

$136

Welcome to Pleasant Cove in Beautiful Boothbay Maine

Boothbay house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 2 match: Car not required, Waterfront

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Price per night from

$327

Maine Bed & Boat, MAZU

Damariscotta yacht

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Car not required, Waterfront

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Price per night from

$338

Ocean Waterfront - Walk to Pemaquid Light

New Harbor house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Car not required, Waterfront

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Price per night from

$369

1 of 2 match: Car not required, Waterfront

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Price per night from

$299

Maine Cottage, Mid-Coast Maine

South Bristol cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Car not required, Waterfront

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Price per night from

$161

Rustic Lakeside Lodge and Four Cabins-13 bedrooms

Jefferson lodge

  • 10 bedrooms
  • 9 bathrooms
  • sleeps 26

1 of 2 match: Car not required, Waterfront

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Price per night from

$1,213

Ocean Front Cottage on Penobscot Bay

Belfast cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Car not required, Waterfront

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Price per night from

$322

Working Lighthouse on Picturesque Island in Maine

Saint George lighthouse

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

1 of 2 match: Car not required, Waterfront

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Price per night from

$1,721

Waterfront Home on Scenic Cove

Harpswell house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Car not required, Waterfront

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Price per night from

$184

Beautiful Seaside Island Home

Long Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Car not required, Waterfront

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Price per night from

$459

Sunset Chalet

Belgrade chalet

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Car not required, Waterfront

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Price per night from

$573

Private Oceanfront Beach House

Georgetown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Car not required, Waterfront

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Price per night from

$574

SkyView treehouse

Belgrade tree house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Car not required, Waterfront

1 of 2 filters match

Price per night from

$686

K2 Lake Paradise

Windham cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Car not required, Waterfront

1 of 2 filters match

Price per night from

$287

Family Friendly Cottage on Androscoggin Lake

Leeds cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Car not required, Waterfront

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Price per night from

$344

Classic Oceanfront Cottage on Orr's Island

Orrs Island cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Car not required, Waterfront

1 of 2 filters match

Price per night from

$320

Charming oceanfront cottage

Cape Neddick cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Car not required, Waterfront

1 of 2 filters match

Price per night from

$320

South Bristol Boathouse

South Bristol house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Car not required, Waterfront

1 of 2 filters match

Price per night from

$301

Quintessential Rustic Maine Oceanfront Cottage with Sunset Views

Tremont cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Car not required, Waterfront

1 of 2 filters match

Price per night from

$345

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