We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Winter Harbor Cottages

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    R 2 924 Average
    |||
    |||
    R 0R 14 000+
    Suitability
    More filters
    Travellers to Winter Harbor are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    8 Matching Rentals in the Winter Harbor AreaView all 23 rentals
    Sort by:
    Default
    Schoodic Point Cottage1 / 19
    (2)Excellent
    Winter Harbor
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Winter Harbor
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    The following rentals are within 10 kilometres of Winter Harbor.
    Brookhouse: A Cottage by the Sea1 / 21
    (4)Excellent
    Prospect Harbor
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Prospect Harbor
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Patio
    • Grill
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PROPERTY OVERVIEW Set on the pristine Schoodic Peninsula, this restored 4BR/2BA cottage provides the ultimate New England retreat. Originally built in 1900, this two-story home boasts original charm paired with beautiful modern upgrades. Your quintessential Maine waterfront getaway features two...
    View all property information
    Location Information
    04669, Prospect Harbor, Gouldsboro
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Charming Waterfront Winter Harbor Cottage w/Views!1 / 24
    (1)Average
    South Gouldsboro
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Ocean Views
    • Balcony
    • Cable/satellite TV
    • Mountain Views
    • Waterfront
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 August 2018
    There is a lot to like at this vacation cottage (more of a mansion, really). The setting is spectacular. The cottage sits on bluffs overlooking a bay with an island and the...
    See all reviews
    About this property
    **Please note that the owners also have a chalet vacation rental unit on the 13 acre property; other travelers may be present during your stay.** Experience the ultimate retreat at this 4-bedroom, 4.5-bath cottage in Winter Harbor! Fondly known as ‘Summer Harbor Cottage,’ this home began as a...
    View all property information
    Location Information
    04693, South Gouldsboro, DownEast and Acadia Maine
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    Make Enquiry
    Birch Harbor
    1 Bedroom, 1 Bathroom, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Waterfront
    • DVD Player
    • Ocean Views
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discover the rocky shorelines and charming Prospect Harbor village when you stay at this 1-bedroom + loft, 1-bathroom vacation rental cottage! With 2.5 acres of wooded property and accommodations for 8, this home is the perfect peaceful retreat. Look forward to falling asleep to the sound of the...
    View all property information
    Location Information
    04669, Birch Harbor, Gouldsboro
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 8
    Make Enquiry
    Prospect Harbor
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • DVD Player
    • Waterfront
    • Balcony
    • Central Heating
    • Parking
    • Wi-Fi
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sitting back 100 feet off the Atlantic Ocean, Dragonwood Castle offers 200 feet of water frontage with glorious sunset reflections across the bay onto the Prospect Harbor Lighthouse. Inside its 2,100 square-feet are 3 decorative levels of living space, plus a small turret that overlooks the ocean...
    View all property information
    Location Information
    04607, Prospect Harbor, Gouldsboro
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Make Enquiry
    Prospect Harbor
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • Balcony
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note the homeowner lives on site, in a completely separate unit and may be present during your stay* Explore Maine’s scenic coastline from this 1-bedroom, 1-bath Prospect Harbor vacation rental cottage that hosts 3. Situated on the shores of the Schoodic Peninsula, natural beauty and...
    View all property information
    Location Information
    04613, Prospect Harbor, Gouldsboro
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    Save time - get the best Winter Harbor rentals sent straight to your email!
    Get the List
    List your property
    Owner log in