Osprey Overlook: Peaceful Riverfront Retreat

  • Welcome to Osprey Overlook!
    Welcome to Osprey Overlook!
  • Spacious main floor with living room, dining area and kitchen
    Spacious main floor with living room, dining area and kitchen
  • Views of the river
    Views of the river
  • Room for everyone to gather while you cook and enjoy meals together
    Room for everyone to gather while you cook and enjoy meals together
  • Well equipped kitchen
    Well equipped kitchen
  • Entrance hall - large area for shoes, coats and gear!
    Entrance hall - large area for shoes, coats and gear!
  • Stairs are required to enter the main living area
    Stairs are required to enter the main living area
  • Hallway to the main living area
    Hallway to the main living area
  • Cozy nooks to read one of the hundreds of books provided in the home!
    Cozy nooks to read one of the hundreds of books provided in the home!
  • Gather to play games in the living room
    Gather to play games in the living room
  • Main floor has a mini split (heating in winter/cooling in summer)
    Main floor has a mini split (heating in winter/cooling in summer)
  • Dining area
    Dining area
  • Deck is accessible in the warmer months
    Deck is accessible in the warmer months
  • Main floor bedroom with queen bed and a mini split (heating in winter/cooling in summer)
    Main floor bedroom with queen bed and a mini split (heating in winter/cooling in summer)
  • First floor bathroom with shower/tub combo
    First floor bathroom with shower/tub combo
  • Stairs to the primary bedroom
    Stairs to the primary bedroom
  • Primary bedroom with a queen bed. The bedroom is a loft style and overlooks the main living area.
    Primary bedroom with a queen bed. The bedroom is a loft style and overlooks the main living area.
  • Sitting area that overlooks main floor
    Sitting area that overlooks main floor
  • View from primary bedroom
    View from primary bedroom
  • View from primary bedroom
    View from primary bedroom
  • Primary bathroom en-suite with shower and separate toileting area
    Primary bathroom en-suite with shower and separate toileting area
  • Primary en-suite shower
    Primary en-suite shower
  • Stairs to finished lower level
    Stairs to finished lower level
  • Many books to choose from!
    Many books to choose from!
  • Lower-level full bathroom with shower
    Lower-level full bathroom with shower
  • Lower level bedroom with queen bed
    Lower level bedroom with queen bed
  • Twin beds in the lower-level TV/Family room
    Twin beds in the lower-level TV/Family room
  • Lower-level TV/Family room - only TV in the house is on this level. There is also access to the backyard.
    Lower-level TV/Family room - only TV in the house is on this level. There is also access to the backyard.
  • Peaceful water views - conducive to kayaking and fishing but not swimming.
    Peaceful water views - conducive to kayaking and fishing but not swimming.
  • Experience all that beautiful Westport Island has to offer at Osprey Overlook!
    Experience all that beautiful Westport Island has to offer at Osprey Overlook!
$350-750/night
3 Bedrooms • 3 Baths • Sleeps 2-8
Allows pets Internet Waterfront (more...)

Hosted by Of Sea and Pine; Maine Vacation Rentals, Osprey Overlook on Westport Island is the kind of place people envision when they dream of a Maine coastal escape. The home’s waterfront location instantly sets it apart—life here flows with the rhythm of the river.

🔑Key Features
-Stunning riverfront location with water views throughout the home
-Deck perfect for lounging, dining, or simply soaking in the peaceful surroundings
-Open-concept living room, kitchen and dining area with cathedral ceilings and abundant natural light
-Three bedrooms and three bathrooms across 3 levels – ideal for families or groups
-Expansive yard for games, lobster dinners or peaceful moments alone
-Private and peaceful setting on Westport Island with convenient access to nearby coastal towns
-Ideal for year-round getaways, from summer vacations to cozy winter retreats
-Dog-Friendly (with owner approval; see pet policy below)

Please Note: Ideal for kayaking, and fishing, but this is NOT a designated swimming area. A vehicle is required, as the area is rural and rideshare services are not available.

🏠 Home Layout
Main Level:
Open-concept kitchen, dining, and living area with cathedral ceilings and water views - mini split (heating/cooling)
1 bedroom with queen bed and mini split
Full bathroom with shower/tub combo
Access to deck

Upper Level:
Primary bedroom with queen bed, en-suite bathroom (walk-in shower) and river views. The primary bedroom is a loft style bedroom and overlooks the primary living area.

Lower Level:
One additional bedroom with a queen bed
Full bathroom (walk-in shower)
Lounge/TV room area with two twin beds and access to the yard

Fans are available in every room, and the home remains cool with the coastal breeze and open windows. Mini splits in main living area and main floor bedroom provides cooling.

Full Description:
Each day unfolds with the sights and sounds of nature: soaring eagles and ospreys from a nearby nesting preserve sweep overhead, while lobster boats and tall ships drift past in the morning light. Evenings bring peaceful sunsets, the gentle movement of tides, and the occasional loon stopping by for a visit.

The home’s connection to the water goes far beyond a scenic view—it’s a fully immersive experience. Whether you're kayaking, fishing, or simply relaxing by the river, the natural beauty surrounding the home is always close at hand.

Whether you're seeking a classic summer waterfront getaway or a cozy, restorative retreat during the quieter months, Osprey Overlook is more than just a vacation rental—it's a tranquil riverfront haven where time slows down and nature sets the scene. From savoring a lobster dinner on the deck to sipping coffee at sunrise or exploring Maine’s charming nearby towns, this home offers a uniquely memorable experience in every season.

📍 Location & Local Charm
Westport Island offers a rare blend of rural seclusion and easy access to some of Midcoast Maine’s most beloved destinations. The island itself is quiet and relaxed, with the soothing rhythm of the river setting the pace.

Nearby Towns to Explore:
Wiscasset – Antique shops, charming cafes, and the famous Red’s Eats (15 minutes away)
Boothbay Harbor – A classic coastal town with sailing tours, shopping, and waterfront dining (30 minutes away)
Damariscotta – Known for oysters, bookstores, and local art galleries (45 minutes away)
Bath – Historic shipbuilding town with museums and a beautiful downtown (15 minutes away)
Brunswick – Home to Bowdoin College, restaurants, and cultural attractions (30 minutes away)

🌅 Things to Do Nearby
-From scenic hikes and fresh-caught seafood to rich local history, the area offers something special for every kind of traveler—nature lovers, foodies, and history buffs alike.
-Kayaking right from the property (Kayaks not provided but can be rented locally)
-Coastal hikes at nearby preserves and trails
-Lobster shacks and seafood spots throughout the region
-Local farmers markets for fresh produce and artisanal goods

A complete guidebook will be provided with detailed recommendations for dining, attractions, hikes, and more!

♿ Accessibility
There are stairs to access the home and multiple levels inside. It may not be ideal for those with limited mobility.

🚗 Parking
Ample parking is available for up to 4 vehicles in the private driveway.

💤 Sleeps
Up to 8 guests comfortably
3 bedrooms and 3 full bathrooms

Neighborhood Notes:
-This is a friendly community with neighboring homes nearby.
-You may hear children playing, neighbors chatting, and dogs barking
-Please respect quiet hours: 9 PM – 7 AM

Dogs are welcome with prior approval and must meet the following requirements:
• Maximum of 2 dogs, each under 60 lbs
• Dogs must be at least 1 year old with up-to-date vaccinations
• Owners must pick up after pets and dispose of waste
• Dogs must be leashed in accordance with local laws
• No dogs allowed on furniture or bedding
• Dogs must be crated if left unattended

Westport, Maine

Property Type House
Accommodation Entire Home
House Rules
  • Maximum occupancy: 8
  • Children welcome
  • Infants welcome
  • Smoking not allowed
  • Wheelchair inaccessible
  • Minimum age of primary renter: 25
  • Pets welcome
Setting & View
  • Water View
  • Waterfront
  • River View
General
  • Air Conditioning
  • Linens Provided
  • Towels Provided
  • Washing Machine
  • Clothes Dryer
  • Hot Water
  • Hair Dryer
  • Wifi
  • Ceiling Fans
  • Laptop Friendly Workspace
  • Basic Soaps
  • Paper Towels
  • Shampoo
  • Toilet Paper
  • Hangers
  • Private Entrance
  • Hair Conditioner
  • Clothing Storage (closet or wardrobe)
  • Portable Fans
Kitchen
  • Kitchen
  • Refrigerator
  • Stove
  • Oven
  • Dishwasher
  • Dishes & Utensils
  • Spices/Pantry Items
  • Coffee Maker
  • Toaster
  • Freezer
  • Blender
  • Pots & Pans
  • Kitchen Island
  • Dining Table
  • Baking Sheet
  • Barbeque/Grill Utensils
  • Coffee
  • Wine Glasses
Bathrooms 3 Baths
  • Primary Floor Bathroom – Combination Tub/Shower, Toilet
  • 2nd Bathroom – Shower, Toilet
  • 3rd Bathroom – Shower, Toilet
Sleeping Arrangements 3 Bedrooms, sleeps 2-8
  • Primary Bedroom – 1 Queen Bed
  • Second Bedroom – 1 Queen Bed
  • 3rd Bedroom – 1 Queen Bed
  • Basement Lounge – 2 Twin Beds
Entertainment
  • Television
  • Books
Outdoor
  • Outdoor Grill
  • Deck/Patio (uncovered)
  • Lawn/Garden
  • Private Yard
  • Outdoor Seating
Vehicles
  • Parking
  • Free Parking
Theme
  • Family
Leisure
  • Antiquing
  • Bird Watching
  • Eco Tourism
  • Whale Watching
  • Boating
  • Shopping
  • Wildlife Viewing
  • Water Sports
Sports & Adventure
  • Fishing
  • Hiking
  • Kayaking
Safety
  • Carbon Monoxide Detector
  • Fire Emergency Contact
  • Fire Extinguisher
  • First Aid Kit
  • Medical Emergency Contact
  • Exterior Lighting
  • Police Emergency Contact
  • Smoke Detector
  • Cleaning Products
Expectations
  • Requires Stairs
  • Near Lake, River, or Water Body