Osprey Overlook: Peaceful Riverfront Retreat | House in Westport

New |   Pet Friendly   4 Bedrooms  3 Bathrooms  8 Guests
Wiscasset House | Osprey Overlook: Peaceful Riverfront Retreat

4 Bedroom House in Wiscasset, Westport

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

Osprey Overlook: Peaceful Riverfront Retreat is located in Wiscasset. Osprey Overlook: Peaceful Riverfront Retreat provides accommodation, featuring Air Conditioner, Wellness Facilities, Internet, among other amenities. This House features Air Conditioner, Wellness Facilities, Internet, to make your stay a comfortable one.

Osprey Overlook: Peaceful Riverfront Retreat has 4 Bedrooms , 3 Bathrooms, and max occupancy of 8 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Wiscasset has interesting places to visit. If you want to learn more about the House in Wiscasset, such as places to visit and things to do nearby, you can check below to learn more.

Show more
OneKey Logos

This Property is OneKey Eligible

Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.

JOIN TODAY

Amenities

Air Conditioner
Parking
Pet Friendly
TV
Balcony/Terrace
Security/Safety
Bedding/Linens
Wellness Facilities
Barbecue/Outdoor Cooking
Child Friendly
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Air conditioning
Bathrooms
  • Towels provided
  • Bathtub or shower
  • Hair dryer
Bedroom
  • Bed sheets provided
  • Dining table
Kitchen
  • Kitchen island
  • Cookware/dishes/utensils
  • Oven
  • Dishwasher
  • Toaster
  • Coffee/tea maker
  • Spices
  • Refrigerator
  • Stovetop
Laundry
  • Washing machine and dryer
Parking
  • Onsite parking
  • Car recommended
Pet Friendly
  • Pet friendly
Accessibility
  • Smoke-free property
Activities
  • Ecotours nearby
  • Whale watching nearby
  • Hiking/biking trails nearby
  • Kayaking nearby
  • Fishing nearby
  • Wildlife and game walks nearby
  • Birdwatching nearby
  • Hiking nearby
  • Power boating nearby
Entertainment
  • TV
  • Books
General
  • Unit size: 2532 sq ft (235 sq m)
  • English
  • On the waterfront
Internet
  • WiFi available
Outdoors
  • Barbecue grill
  • Deck or patio
  • Garden
Security/Safety
  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • Fire extinguisher
  • First aid kit
  • Smoke detector installed (host has indicated there is a smoke detector on the property)

Policies

Check-in
Check-in time starts at 4:00 pm minimum check-in age: 25
Check-out
Check-out before 10:00 am
Child Policy
Children are welcome.
Event Policy
No events allowed
Pet Policy
Pets allowed service animals are welcome, and are exempt from fees
Smoking Policy
Smoking is not permitted

Extra-person charges may apply and vary depending on property policy government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher and a first aid kit special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation

Check House Availability
Nightly rates from:
USD511
You will be redirected to  
Hot Deal - It has been viewed 46 times today
Not the right fit? Check out our other properties in Wiscasset
Hidden Gem on Westport Island From US $214
         

10.0 (111 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
High Street Stunner From US $700
         

|
10.0 (1 Review)
House
  • Balcony/Terrace
  • Security/Safety
  • Sports/Activities
The Squire Tarbox Inn From US $327
         

9.6 (22 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Riverfront Coastal Escape with Deep Water Dock! From US $642
         

|
10.0 (1 Review)
House
  • Parking
  • Accessibility
  • Security/Safety
Westport Waterfront From US $552
         

|
9.5 (2 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Periwinkle Cottage From US $391
         

|
9.4 (6 Reviews)
House
  • Balcony/Terrace
  • Security/Safety
  • Sports/Activities
Beautiful Wiscasset Home 5 AC units, sleeps 16 From US $567
         

10.0 (23 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Maine Village Properties 5 AC units, sleeps 16 From US $640
         

Tiny A-Frame Romantic Getaway From US $333
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Doggett Castle Guest House From US $341
         

9.8 (18 Reviews)
House
  • Parking
  • Pet Friendly
  • TV