Updating...

Enter dates for more accurate prices

Winter Harbor Rentals

Filter

Bedrooms

  • Any
  • 1+ Bedrooms
  • 2+ Bedrooms
  • 3+ Bedrooms
  • 4+ Bedrooms
  • 5+ Bedrooms
  • 6+ Bedrooms
  • 7+ Bedrooms
  • 8+ Bedrooms
  • 9+ Bedrooms
  • 10+ Bedrooms
  • 11+ Bedrooms
  • 12+ Bedrooms
  • 13+ Bedrooms
  • 14+ Bedrooms
  • 15+ Bedrooms

Price range

Per night

$10 - $500

Winter Harbor Rentals

11 condos

Down East Maine Modern, Well Equipped Cottage in Heart of Coastal Winter Harbor

Winter Harbor cottage

2 bedrooms / 2 bathrooms / Sleeps 5

$139

1 / 10

ACADIA National Park. Walk to Ocean, Restaurants. PRIVATE Deck w/Mountain View

Winter Harbor house

3 bedrooms / 2 bathrooms / Sleeps 6

“Great family stay” We have 4 generations staying here for several nights. First of all the owners were wonderful to work with and the home had everything we needed to have a wonderful time. There was plenty of space for everyone and we enjoyed walking

$129

1 / 58

Gerrish Vacation Rentals

Winter Harbor apartment

1 bedroom / 1 bathroom / Sleeps 2

$145

1 / 9

Gerrish Vacation Rentals

Winter Harbor apartment

1 bedroom / 1 bathroom / Sleeps 2

$145

1 / 8

Acadia, Schoodic Peninsula, Henry's Cove Home

Winter Harbor house

3 bedrooms / 1 bathroom / Sleeps 6

$150

1 / 15

NEW! Cozy 3BR Waterfront Cabin in Winter Harbor!

Winter Harbor log cabin

3 bedrooms / 2 bathrooms / Sleeps 6

$155

1 / 24

Fred's Place

Winter Harbor apartment

1 bedroom / 1 bathroom / Sleeps 2

$75

1 / 21

Spectacular Oceanfrontage & Private Cove

Winter Harbor house

2 bedrooms / 2 bathrooms / Sleeps 6

$214

1 / 24

Guptill Cottage on Schoodic Point, Winter Harbor

Winter Harbor house

3 bedrooms / 1 bathroom / Sleeps 5

$179

1 / 24

Captain Bickford House (Arthur Frommer was here)

Winter Harbor house

2 bedrooms / 1 bathroom / Sleeps 6

$95

1 / 26

Captain Guptill House steps from the waters edge in Winter Harbor

Winter Harbor house

3 bedrooms / 3 bathrooms / Sleeps 6

$221

1 / 21
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more