Holiday houses in Sebago

Vacationland Retreat Lake House

Perfect for families. Newly renovated, luxurious, 3 bedroom/3 bathroom, waterfront house located in Southern Maine's Lakes and Mountains Region. You will have your own, private, shallow lake entry, private wooden dock to use and a floating dock with built-in loungers to swim to and sunbathe on! Our pristine pond is ideal for swimming, paddle boarding, kayaking, fishing and more. House is located near Pleasant Mnt, Bridgton, Sebago Lake, Long Lake, Naples, Saco River, Cranmore Mtn, & Conway, NH.

Sebago Lake waterfront Cottage

This 3 acre Sebago Lake property has an adorable 2 bed/1 bath cottage. It's a perfect family destination for swimming, boating, and fishing. Perfectly located for a day trip to Portland, Old Orchard Beach, Kennebunkport, Freeport, Kittery and North Conway, NH. Wake up to the beautiful sunrise with a cup of coffee or watch the sunset from the front porch. The cottage has a full kitchen, laundry, and two TV areas. In the winter snowmobile, snowshoe, ice skate, or cross-country ski in the area

Modern lakefront home on Sebago Lake in Maine

** New photos showcasing refreshed furnishings for 2026! ** Serene and spacious, this lakefront house has all of the comforts that make for a relaxing getaway. Looking for a more active vacation? Its ideal waterfront setting is the perfect launch point for a kayak adventure, a swim, or a casual hang on a float. [Note: AirBNB is auto-calculating a 13-min walk to Sebago Lake proper as its system does not recognize the "Sebago Cove" section of the lake. The house is lakefront w/ direct access!]

Tri-Lake Escape: Brandy Pond

Tri-Lake Escape offers the ultimate waterfront getaway with direct access to Brandy Pond, Long Lake, and Sebago Lake. This charming retreat is perfect for families, couples, and outdoor enthusiasts looking to relax and explore. Enjoy stunning lake views, a private dock, and endless activities, including swimming, boating, fishing, and kayaking. Unwind on the spacious deck, gather around the fire pit, or take a short drive to downtown Naples for dining, shopping, and local attractions.

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

Private 4-Season Home – Quiet Side of Sebago Lake

Close to wedding venues! Guests have the entire first floor, deck/grill/fire pit, yard & private entrance. 4 Season contemporary home built in the 80’s. Open plan. 5 minutes from: Autumn Lane Estate Camp O-AT-KA Nason’s Beach Boat launch Sandwich Shop 10 minutes from: Garden Gate at Haley Farm Naples Sebago Lake State Park Restaurants Entertainment shopping Churches Seaplane rides Boat rentals 30/60 min: Stone Barn Leaf Peeping Skiing/Snowboarding Outlet Shopping N Conway NH

Barrett’s Cabin-Lakes Region-Private Trails

Welcome to Barrett's Cabin located in the foothills of the White Mountains with water views of Hancock Pond, 50 minutes to Portland, 35 to North Conway and 15 to Bridgton and Pleasant Mountain. Open concept first floor, 2 bedrooms, 1 bathroom, Carriage House has 2 bedrooms for an additional $50 per night. Driveway fits up to 6 cars. Enjoy outdoor patio, shower, fire-pit, private mini hiking trail system and quick access to snowmobile trails and public boat launch 1/3 mi away.

Rustic, cozy cabin on Sebago Lake. A hidden gem.

Step out of the screened in patio to lakeside relaxation. Dive into crystal waters, snorkel or float with a cool beverage. Kayak or canoe out to Turtle Cove and enjoy the wildlife in this natural waterway teeming with birds to include our resident Blue Heron, ducks, geese, and loons who make this place their home. We have the fortune of bald eagles in several tall pines. Turtles sunning on doting rocks and lily pads in bloom greet us each day. It is a natural water landscape.

The Chalet~ 4 bed Lakefront Family Vacation

Welcome to your secluded slice of paradise on the shores of Sebago Lake! Nestled amidst towering pines and overlooking the tranquil waters of Seabgo Cove, our 4-bedroom waterfront chalet promises a serene escape like no other. Whether you're seeking adrenaline-pumping thrills from the local excursions, or peaceful moments surrounded by nature and a book, The Chalet offers endless opportunities for unforgettable experiences and cherished memories in the heart of Naples.

Best Ski & Lake House

Spectacular, expansive, state-of-the-art log cabin—your ultimate four-season escape. Winter ski trips (just 25 minutes to Pleasant Mountain, formerly Shawnee Peak), summer fun (beaches & watersports galore), & unforgettable year-round gatherings. Chef’s kitchen with two ovens, dining for eight + bar seating, sleeps up to 12 (with 2 king beds), two living rooms, and abundant outdoor dining & lounge space, including a playground - designed to make lasting memories!

Trickey Moose Family Retreat | Fire Pit Kayaks

Enjoy 4 seasons of fun with shared access to Trickey Pond and use of 2 kayaks, large deck, fire pit, gas grille, backyard, wood stove, air hockey, ping pong table, close to skiing, snowmobile trails, boating, hiking & much more. Beautiful open concept house with loft and cathedral ceilings is perfect for large families with a well appointed kitchen, fast Wi-Fi, laptop friendly workspace, central AC, jacuzzi, free parking.

Quiet, Cozy Cabin Tucked in the Woods

Escape to a peaceful, secluded cabin perfect for relaxing with family and friends. Just 1/4 mile from Camp Micah, enjoy scenic hiking with Bald Pate Mountain’s trail right across the street. Visit nearby farms and orchards, or take a quick 15-minute drive to Sebago Lake and Naples. In winter, Pleasant Mountain skiing is only 20 minutes away. The perfect year-round Maine getaway for adventure or pure tranquility.