But don't worry, we're on call to make sure your stay goes smoothly.But don't worry, we're on call to make sure your stay goes smoothly.
5 bedrooms2+ bathroomsSleeps 10
Popular amenities
Garage parking available
Kitchen
Washing machine
Air-conditioning
Deck or patio
Internet access
Explore the area
Freeport, ME
Bradbury Mountain State Park
Place, Bradbury Mountain State Park
3 min drive
Wilbur's of Maine Chocolate Confections
Place, Wilbur's of Maine Chocolate Confections
6 min drive
LL Bean Flagship Store
Place, LL Bean Flagship Store
8 min drive
Portland, ME (PWM-Portland Intl. Jetport)
Airport, Portland, ME (PWM-Portland Intl. Jetport)
25 min drive
Rooms & beds
5 bedrooms (sleeps 10)
Bedroom 1
1 King Bed
Bedroom 2
1 Queen Bed
Bedroom 3
2 Single Beds
Bedroom 4
1 King Bed
Bedroom 5
1 Queen Bed
2 bathrooms, 1 half bathroom
Bathroom 1
Toilet
Bathroom 2
Bathtub or shower · Toilet
Bathroom 3
Toilet · Shower only
Spaces
Deck or patio
Kitchen
About this property
Luxury Waterfront Vacation Rental in South Freeport - Private Dock on Casco Bay
Welcome to Little Anchor, a beautifully renovated waterfront vacation rental in South Freeport, Maine, offering sweeping views of Casco Bay, a private dock, and an exceptional coastal Maine retreat just minutes from Freeport and Portland. Located on scenic Castle Road in the charming village of South Freeport, this thoughtfully renovated home combines luxury comfort, modern design, and classic Maine coastal charm. With expansive water views, an open floor plan, and abundant natural light, Little Anchor is the perfect destination for families or small groups seeking a relaxing Maine coastal vacation. ________________________________________
Stunning Waterfront Views of Casco Bay. Nearly every room in the home enjoys panoramic views of Casco Bay, while others overlook a peaceful forest setting with glimpses of Spar Cove. The home’s open layout was designed to maximize natural light and showcase the spectacular waterfront scenery. Guests can relax in the spacious living room and media room, both designed for comfort and gathering after a day exploring the Maine coast. Step outside to a beautiful south-facing stone patio overlooking the bay, perfect for outdoor dining, morning coffee, or watching the sunset over the water. The large lawn leads directly to Little Anchor’s private dock, providing easy access to the tidal waters of Casco Bay when tides allow. ________________________________________
Comfortable Accommodations for Families and Groups. Little Anchor comfortably accommodates up to 10 guests across five well-appointed bedrooms, making it ideal for family vacations, couples traveling together, or small retreats on the Maine coast. Each bedroom is thoughtfully designed with comfortable bedding, ample storage, and peaceful views.
Bedroom Layout Main Level • King Bedroom – Bay Views • Queen Bedroom – Forest Views • Twin Bedroom – Forest Views Lower Level • King Bedroom – Bay Views • Queen Bedroom – Bay Views A private home office provides a quiet space for guests who need to work remotely while enjoying a Maine getaway. ________________________________________
Modern Amenities for a Relaxing Coastal Stay. The home features modern conveniences designed for comfort and relaxation: • High-speed WiFi throughout the home • Three Smart TVs in the living room, media room, and twin bedroom • Peloton bike • Central air conditioning • Spacious two-car garage • Large yard with direct waterfront access Whether you're unwinding after a day on the water or enjoying a quiet evening indoors, Little Anchor offers everything needed for a memorable stay. ________________________________________
Private Dock and Waterfront Activities. Little Anchor sits directly on the tidal waterfront of Casco Bay, making it an ideal base for boating, kayaking, paddleboarding, and coastal exploration. Guests can easily rent kayaks or paddleboards locally and launch directly from the private dock located just steps from the lawn. The protected waters around South Freeport offer incredible opportunities to experience Maine’s coastal beauty, marine wildlife, and scenic islands. ________________________________________
Walk to South Freeport Village. One of the most special aspects of Little Anchor is its walkable location in South Freeport Village. Within a short stroll, you’ll find: • Harraseeket Lunch & Lobster – famous for some of the best lobster rolls in Maine • South Freeport Village Market – groceries, prepared foods, and essentials • Harraseeket Yacht Club • Brewers and Stroud’s Marine Boatyards For sailing enthusiasts, the Portland Yacht Club is also a short drive away. ________________________________________
Explore Freeport, Portland, and Coastal Maine. Little Anchor is perfectly located for exploring some of the best destinations in coastal Maine.
Nearby attractions include: • Downtown Freeport (5 minutes) – LL Bean, shopping, restaurants • Freeport Golf Club (10 minutes) • Yarmouth Village (10 minutes) Charming shops and restaurants • Oyster Farms in Surrounding Areas • Portland Old Port District (20 minutes) • Beaches, island cruises, and scenic coastal drives
Travel is easy with Portland International Jetport only 25 minutes away. Concord Coachlines Bus goes directly to and from Logan Airport and South Station in Boston. Amtrak train station is in Freeport, just 5 minute’s drive and conveniently provides access to destinations both North and South. ________________________________________
The Perfect Coastal Maine Getaway. With its stunning Casco Bay views, private dock, modern renovations, and unbeatable South Freeport location, Little Anchor offers a truly special waterfront vacation rental experience in Maine. Whether you're planning a family vacation, boating getaway, or relaxing coastal retreat, this elegant home provides the perfect setting to experience the beauty of the Maine coast.
Welcome to Little Anchor — your private waterfront escape in South Freeport, Maine.
Here is a link for more information and a Floor Plan! https://www.waterfrontrentalhome.com/ https://cdn.openhomesphotography.com/cms/29-castle-road.1ee20085-9abc-6f68-8104-028e91101f1d/46742567-eff8-430a-910a-420ad5c61d82.pdf
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Air conditioning
Gym
Ocean view
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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
Parties and events (including family gatherings) are allowed on site. Maximum attendees: 25
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
About the area
Freeport
Freeport is home to this holiday home. Golf Learning Center and Gilsland Farm Audubon Center are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Wilbur's of Maine Chocolate Confections and Wolfe's Neck Farm. Greely Center for the Arts and Orion Performing Arts Center are also worth visiting. Spend some time exploring the area's activities, including golfing.
Bradbury Mountain State Park - 3 min drive - 2.2 km
Eartha - 6 min drive - 6.5 km
Wilbur's of Maine Chocolate Confections - 6 min drive - 5.0 km
Winslow Memorial Park - 7 min drive - 4.7 km
LL Bean Flagship Store - 8 min drive - 7.2 km
Getting around
Freeport Station - 8 min drive
Portland, ME (PWM-Portland Intl. Jetport) - 31 min drive
Restaurants
Circle K - 8 min drive
Cumberland Farms - 8 min drive
McDonald's - 8 min drive
Dunkin' - 8 min drive
Dunkin' - 8 min drive
Frequently asked questions
Is Luxury Waterfront Vacation Rental in South Freeport - Private Dock on Casco Bay pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Luxury Waterfront Vacation Rental in South Freeport - Private Dock on Casco Bay?
As of 27 April 2026, prices found for a 1-night stay for 2 adults at Luxury Waterfront Vacation Rental in South Freeport - Private Dock on Casco Bay on 23 June 2026 start from NZ$1,364, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Luxury Waterfront Vacation Rental in South Freeport - Private Dock on Casco Bay?
On-site parking is available at the property.
What time is check-in at Luxury Waterfront Vacation Rental in South Freeport - Private Dock on Casco Bay?
Check-in begins at 3:00 PM.
What time is check-out at Luxury Waterfront Vacation Rental in South Freeport - Private Dock on Casco Bay?
Checkout is at 11:00 AM.
Where is Luxury Waterfront Vacation Rental in South Freeport - Private Dock on Casco Bay located?
Situated in Freeport, this holiday home is steps from Casco Bay and within 3 mi (5 km) of Bradbury Mountain State Park and Wilbur's of Maine Chocolate Confections. Eartha and Freeport Historical Society are also within 6 miles (10 km).