Cozy Winter Retreats on Peaks Island: Stunning Waterfront & Secluded Getaways

Reflecting on a Magical Winter on Peaks Island: Why Now’s the Time to Plan Your Next Off-Season Escape

Wintertime on Peaks Island, Maine, brought with it a quiet beauty that only a select few truly get to experience. This past season, several of our vacation properties transformed into cozy, long-term winter havens—welcoming guests who chose to slow down, recharge, and embrace the peaceful rhythm of island life. Whether it was remote workers seeking focus, couples enjoying fireside evenings, or writers and creatives drawing inspiration from the ever-changing seascape, winter on Peaks proved to be a deeply restorative experience.

While spring brings new life to the island, we’re already looking ahead—because the best winter stays require early planning. If you've ever dreamed of watching snow fall over Casco Bay or enjoying the solitude of quiet beaches and scenic hikes all to yourself, a long-term winter rental might be exactly what you're looking for. Now is the perfect time to reach out, explore our available properties, and reserve your spot for next season.

From fully equipped kitchens and high-speed internet to breathtaking views and homey comfort, our winter rentals offer everything you need to settle in and truly experience the magic of off-season living on Peaks Island. Curious about availability or ready to start planning your stay? Scroll to the bottom of this post for full booking details or click here.

Gorges Sunset One – Peaks Island Water View Condo

Imagine waking up to breathtaking views of Casco Bay, sipping a hot cup of coffee on your private outdoor deck, and embracing the serene beauty of Peaks Island in winter.

Gorges Sunset One is a luxurious, newly built condo that offers all the comforts of home while immersing you in an unforgettable island experience.

Why You'll Love It:

Location, Location, Location – Just a short walk to the ferry, restaurants, and market, yet perfectly tucked away for privacy.
Modern Amenities – New construction means everything is pristine, from the fully equipped kitchen to the in-unit laundry.
Year-Round Beauty – Whether blanketed in snow or kissed by the winter sun, Casco Bay provides a stunning backdrop to your stay.
Spacious Comfort – With a queen bed in one bedroom and twin beds in the other, it's the perfect retreat for couples or small families.

This Peaks Island gem is ideal for a long weekend getaway or an extended stay, providing the perfect balance of luxury and island charm.

Gorges Sunset Two – Peaks Island Water View Condo

For those who can’t get enough of waterfront views, Gorges Sunset Two offers another exceptional winter escape on Peaks Island. With an expansive deck and a cozy interior, this home is designed to make your winter retreat truly magical.

What Sets It Apart?

Unobstructed Water Views – Watch the winter waves roll in while staying warm and cozy inside.
Ultimate Convenience – A five-minute walk to everything you need, from fresh seafood restaurants to charming local shops.
Cozy & Modern Living Space – With an open-concept layout, in-unit laundry, and a smart TV for your winter movie nights.
Perfect for Short or Long Stays – Available for nightly, weekly, or monthly rentals, allowing you to plan the perfect winter getaway.

If you’re looking for a place to relax and recharge while enjoying scenic beauty, Gorges Sunset Two is the perfect spot.

29 Beach – Spacious Peaks Island Getaway

For those who need a little more space without sacrificing charm, 29 Beach is the perfect winter retreat. This three-story home offers stunning ocean views, a warm and inviting interior, and easy access to Centennial Beach on Peaks Island.

Highlights:

Classic Meets Contemporary – Beamed ceilings and hardwood floors provide a rustic touch, while modern updates ensure total comfort.
Spectacular Views – Gaze out toward Portland and Down the Bay while enjoying the peaceful surroundings.
Perfect for Families or Groups – Three spacious bedrooms accommodate up to seven guests, making it an excellent option for larger groups.
A Cozy Retreat with Work-from-Home Potential – A lofted office space allows for a peaceful and productive getaway if needed.

If your winter escape includes family or friends, 29 Beach is the perfect home to gather, unwind, and enjoy the beauty of the season.

Winter View – A Hidden Peaks Island Sanctuary

Not all winter getaways need a water view to be magical. Winter View is an unexpected treasure tucked away just moments from the island’s bustling center. Surrounded by garden spaces and natural beauty, this recently renovated home is perfect for those looking to relax, read, and recharge.

Why Choose Winter View?

Charming & Secluded – Experience a peaceful retreat while still being close to local attractions.
Thoughtfully Designed – Updated with modern amenities while preserving its natural character.
Cozy Comforts – With three bedrooms (queen, full, and twin beds), this home provides plenty of space to unwind.
Perfect for Quiet Reflection – A porch with rockers, an abundance of books, and a warm interior make this an ideal retreat for winter relaxation.

If you’re seeking a winter hideaway to reconnect with yourself or loved ones, Winter View is your perfect match.

The Dwelling Place – Cozy Peaks Island Cottage with Ample Space

If you’re dreaming of a classic cottage getaway, The Dwelling Place is the perfect winter retreat. With a spacious yard, a fire pit for roasting marshmallows, and a covered front porch, this Peaks Island cottage is an ideal destination for a cozy escape.

What You'll Love:

Quaint Yet Spacious – Offers single-level living with an airy layout, vaulted ceilings, and French doors leading to the patio.
Fully Equipped for Comfort – Thoughtfully curated for a calming, connected stay. With cozy interiors and a peaceful setting, this is a place to slow down, feel grounded, and experience the true rhythm of island life—surrounded by a close-knit, welcoming community.
Close to Everything – Just a six-minute walk to the ferry, restaurants, and market, making island life a breeze. Enjoy the serenity of the island while still being just a scenic 15-minute ferry ride from the vibrant energy of downtown Portland.
Ideal for Families or Small Groups – Two bedrooms and a futon accommodate up to six guests.

For those looking for a charming and peaceful retreat, The Dwelling Place is a winter getaway dream come true.

Book Your Perfect Peaks Island Winter Escape Today

No matter what kind of winter retreat you’re dreaming of—whether it’s a cozy waterfront view, a private beach escape, or a hidden island sanctuary—these Peaks Island properties in Portland, Maine, offer something truly special. From peaceful morning strolls along the shore to crackling fireside evenings, your perfect winter getaway awaits.

These are just a few of the properties we've had available this past winter season. If you're interested in planning ahead for next winter, we’d love to help you find the perfect spot—reach out to see which homes will be available.

Ready to start dreaming? Book your stay now and experience the quiet magic of a Peaks Island winter.