Entire home
Osprey Overlook: Peaceful Riverfront Retreat
Wiscasset vacation home with kitchen
Choose dates to view prices
Photo gallery for Osprey Overlook: Peaceful Riverfront Retreat





Popular amenities
- Pet friendly
- Air conditioning
- Parking available
- Kitchen
Explore the area

Westport, ME
- Monkey C Monkey DoPlace, Monkey C Monkey Do9 min drive
- Wiscasset Historic DistrictPlace, Wiscasset Historic District13 min drive
- Castle TuckerPlace, Castle Tucker13 min drive
- Wiscasset, ME (ISS)Airport, Wiscasset, ME (ISS)9 min drive
Room options
About the area
Wiscasset
On waterfront.Within 6 miles (10 km) of this Wiscasset vacation home, you'll find Monkey C Monkey Do and Castle Tucker. Wiscasset Historic District and Lincoln County Jail Museum are also within 6 miles (10 km).
What's nearby
- Monkey C Monkey Do - 9 min drive - 6.1 km
- Wiscasset Historic District - 13 min drive - 8.6 km
- Castle Tucker - 13 min drive - 8.6 km
- Fort Edgecomb State Historical Site - 16 min drive - 10.8 km
- Waterfront Park - 18 min drive - 18.7 km
Getting around
- Brunswick Station - 27 min drive
- Wiscasset, ME (ISS) - 7 min drive
Restaurants
- Circle K - 7 min drive
- McDonald's - 7 min drive
- Jodie’s Cafe & Bakery - 7 min drive
- Dunkin' - 7 min drive
- Sea Basket - 7 min drive
About this property
Osprey Overlook: Peaceful Riverfront Retreat
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
🔑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
Policies
Check-in
Check-in time starts at 4:00 PM
Minimum check-in age: 25
Check-out
Check-out before 10:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Rules
Guests are required to sign rental agreement; only those on the original reservation may stay overnight
A security deposit of up to $1000 will be held 2 days before arrival and released (if no issues are found) 7 days after departure
Primary guest must be at least 25 years of age. No parties or events; no smoking
Pets
- Pets are welcome
- Service animals are exempt from fees
Children and extra beds
- Children are welcome.
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
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
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
- 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. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit in each accommodation.
Property is also known as
orp5b74190x