Holiday houses in Ring Island

5.0 out of 5 average rating, 98 reviews

A serene lakeside scene is presented with two dark green Adirondack chairs positioned around a fire pit on a grassy area. A wooden dock extends into the lake, with a small boat resting beside it, surrounded by trees that frame the tranquil view.

Cottage in Raymond

Lovely Lakefront Cottage - Book Your Fall GetAway!

Whether you’re craving a peaceful retreat or a winter adventure, this lakefront cottage has everything you need to create unforgettable memories. Cozy up by the fire, snowshoe the lake, or simply soak in the serene beauty of the season. Embrace the charm of winter on the lake, the perfect getaway for families, couples, or solo adventurers. Don't wait for summer to fall in love with this hidden gem. NOTE: Winter & Spring guests should be comfortable navigating winter weather/seasonal conditions.

LocationValueOutdoor spaces

Superhost

A comfortable outdoor space is presented with a grassy area surrounded by trees. Blue chairs are arranged around a fire pit, and large windows of the two-story home reflect the natural light. A sense of privacy is offered by the surrounding foliage.

Cottage in Casco

4.8 out of 5 average rating, 45 reviews

Waterfront Getaway w/ Private Beach (HOT TUB)

Enjoy a cozy home away from home! This sunny 3 bedroom, 1 bath cape comfortably sleeps up to 8 guests right on one of Maine’s premier lakes, Big Sebago Lake. Take in the beautiful views of Kettle Cove from the back yard or go swimming at the private beach, just a 2 minute walk away. Tastefully updated, it offers amenities such as an open entertainment space and exceptional comfort during those hot summer days or cold winter nights. ****HOT TUB is only available in the cold season October-May***

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The master bedroom features a spacious bed with light-colored bedding, complemented by soft pink pillows. Natural light floods the room through sliding glass doors leading to the outdoor area. A rustic barn door adds character and provides access to the adjacent bathroom.

4.87 out of 5 average rating, 106 reviews

Fully Updated Lake View Home on Thomas Pond

Full of light and thoughtful touches, this lake view home on Thomas Pond is perfect for your Sebago Lake getaway. Spend your evenings relaxing or entertaining on the spacious deck and days on the water. Enjoy boating, fishing, swimming and kayaking with access to two association beaches and a boat launch across the street. Perfect for family fun and couples' retreats, this home is a fantastic home base to explore the Lake Region. Minutes to North Windham shopping and 30 minutes to Shawnee Peak.

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The exterior of the Sebago Breeze Lake House reveals a charming shingle-style structure nestled among lush greenery. A spacious lawn leads to a screened porch, offering relaxation space. Stairs provide access to the upper level, while a paved driveway accommodates vehicles.

4.97 out of 5 average rating, 35 reviews

Prime Sebago Lakefront House

The Sebago Breeze Lake House has it all. 185' of private, direct waterfront including a sandy beach with firepit, built-in grill and spacious level lot for all the summer activities. Tie your boat to the giant dock or mooring and enjoy the lake from your own swim float. The calm waters around Dingley Islands lie just offshore. Inside you will enjoy all the updates, 4 bedrooms, 3.5 baths, two separate rec spaces and an airy, screened porch, perfect no mater the weather. The Way Life Should Be!

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A warm and rustic living area features a stone fireplace, with a flickering flame providing a cozy ambiance. Natural wood paneling surrounds the room, complemented by a comfortable leather sofa. A large window reveals a view of the outdoor deck amidst a wooded backdrop.

4.96 out of 5 average rating, 28 reviews

Kettle Cove Beach Access Sebago Lake

Welcome to Kettle Cove Cabin! Located just steps from beautiful Lake Sebago, our charming cabin offers a serene escape from the hustle and bustle of everyday life. With its rustic charm and modern comforts, this retreat is designed to provide you with a home away from home. Spend your day on the lake and watch the sunset by the fire as you make memories that will last forever. 2 min-Point Sebago Golf Course 8 min-Sebago Lake State Park 10 min-Naples Causeway 12 min-Seacoast Adventure

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A calm lake scene reflects clear blue skies dotted with clouds. Pine trees line the shore, while boats are anchored along the water's edge. The surface of the water is smooth, creating a mirror-like effect that enhances the tranquil atmosphere.

4.89 out of 5 average rating, 65 reviews

Sebago Lake family friendly escape w dock, dogs ok

Unwind at our family and pet-friendly Cottage on Sebago Lake located in Kettle Cove, steps away from a neighborhood beach, shared dock, boat launch, and own slip. Enjoy modern comforts, including air conditioning. Grill outdoors and make s’mores by the fire pit in the summer or cozy up inside by the gas fireplace in the winter after skiing, snowmobiling, snow tubing, or ice fishing. Just under 45 minutes to Portland Jet Port, North Conway and minutes away from Point Sebago golf course.

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5.0 out of 5 average rating, 27 reviews

Home in Naples

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.

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4.97 out of 5 average rating, 198 reviews

Home in Naples

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!

FamilyLocationParks

4.89 out of 5 average rating, 9 reviews

NEWLY Remodeled Waterfront Home on Sebago Lake

NEW for 2026- Escape to this newly renovated waterfront home on Sebago Lake. Enjoy stunning sunrise views of the big bay with the calm protection of the cove. The walk-in sandy beach is perfect for swimming, kayaking, and fishing. The backyard offers outdoor dining, a grill, and a fire pit for evenings by the water. With comfortable accommodations for up to 10 adults, and whole house AC, this cozy retreat provides everything you need for a relaxing and unforgettable lakeside getaway.

LocationFamilyWi-Fi

4.91 out of 5 average rating, 67 reviews

A charming home nestled among trees, with a spacious deck extending from the front. Large windows offer views of the serene surroundings, while a pathway leads from the house to the water's edge. The exterior features a mix of natural elements and a carefully maintained yard.

Cottage in Raymond

The Great Escape - Picturesque Sebago Lake

Experience an intimate home with stunning Sebago Lake views. This inviting retreat features 4 bedrooms and 8 beds, ensuring a restful stay for up to 12 guests. The enormous kitchen island is perfect for gathering, whether preparing a family feast or enjoying casual conversations. Snuggle up by the propane fireplace in the living area, or spend evenings around the outdoor firepit, making s’mores under the stars. The breathtaking lake views create a serene backdrop for your vacation.

FamilyLocationHiking

4.93 out of 5 average rating, 183 reviews

A serene lakeside view reveals a wooden dock with a reclining chair near the water's edge. Vibrant autumn leaves frame the scene, contrasting with the clear blue sky and calm lake. Rocky terrain adds natural texture to the tranquil environment, inviting relaxation.

Cabin in Raymond

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.

ValueFamilyHospitality