Vacation Rentals & Cottages in Southwest Harbor

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79 cottages

Andy's Retreat - Heated outdoor pool, Hot Spring jacuzzi, central AC, BBQ

Falmouth house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Heated pool Sea view

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Price per night from

$684

The Point, Where the Land Meets the Sea

Harpswell house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Heated pool Sea view

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Price per night from

$913

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Beach Getaway

Moody cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Sea view, Heated pool

1 of 2 filters match

Price per night from

$286

Kendall Farm Cottages

Perry cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$195

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Birch Harbor boathouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$1,027

Hannah's House - in Bar Harbor, close to Acadia NP, & POOL!

Bar Harbor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Sea view, Heated pool

1 of 2 filters match

Price per night from

$826

Seal Cove Beach Smokeshed Cottages

Grand Manan house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$114

Ocean Waterfront - Walk to Pemaquid Light

New Harbor house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$367

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: Heated pool, Sea view

1 of 2 filters match

Price per night from

$160

Waterfront Home on Scenic Cove

Harpswell house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$183

Quintessential Rustic Maine Oceanfront Cottage with Sunset Views

Tremont cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$343

Captain's Quarters at Captain Bennis House

Sullivan apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$114

Ellenton Cottage on the Cove, Prospect Harbor

Prospect Harbor house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$310

Oceanfront mini home, two decks, with spectacular views.

Meteghan cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$125

Nattuary, a Nordic Spa Retreat on the Bay of Fundy

Gardner Creek guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$209

Classic Oceanfront Cottage on Orr's Island

Orrs Island cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$320

Maine Bed & Boat, NEBI

Damariscotta boathouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$338

Modern Loft with a timeless Ocean View

Port Clyde studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$81

Harbor/ Pound Access & Views from Large Deck

Owls Head house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$154

Quaint cottage with the charm & tranquility one looks for on the Coast of Maine

Tenants Harbor cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$154

Unique, Secluded Home with Pool: Acadia High Tower

Mount Desert house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Sea view, Heated pool

1 of 2 filters match

Price per night from

$864

Charming oceanfront cottage

Cape Neddick cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$319

Minutes from Popham Beach - Cozy Maine Coast Cottage

Phippsburg cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$257

Midcoast Waterfront Maine Home- Direct Waterfront, secluded site.

Cushing house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$310

Charming ocean front cottage in Harpswell

Harpswell cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 2 hours 55 minutes

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$176

Beachfront Cottage on Indian Point

Georgetown cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$314

Bayview Cottage

Welshpool house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$206

Ocean Front Cottage, Harpswell, ME

Harpswell cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$253

Camp Forever

Harpswell studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$314

Seaside Rosehip Cottage Downeast Maine

Jonesport cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$257

Working Lighthouse on Picturesque Island in Maine

Saint George lighthouse

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$1,712

Beautiful Seaside Island Home

Long Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$457

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: Heated pool, Sea view

1 of 2 filters match

Price per night from

$185

SUMMER COTTAGE BY THE SEA

Swans Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$286

Chadwick House

Friendship house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$457

Bay Sunrise Vista Helmet

Portland condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$326

Scenic White Rocks Cottage on the Maine Coast

Georgetown cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Outstanding vacation location on Georgetown Island, Maine” For the past three years, we have vacationed at White Rocks Cottage on Georgetown Island, Maine (not far from Bath) and we highly recommend it. Whether you have children or not, there are plenty of activities in the area for everyone (hiking, boating, fishing, swimming, strolling beaches, shopping & eating in or out) or, you can do nothing but relax and watch the world go by in the comfort of this lovely, private, clean and well furnished home on the Maine Coast. You will certainly not be disappointed in fact, a stay at White Rocks cottage will be a memory you will treasure forever!

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$200

Bungalow On The Bay

Saint John house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Heated pool, Sea view

1 of 2 filters match

Price per night from

$146

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rentals in Southwest Harbor

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