Holiday houses in Ring Island

Luxury Year-round Hobbit House w/ private hot tub

Fern Hollow is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

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!

Dreamy Post&Beam Hideaway Near Portland & Freeport

Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.

Cabin at Sunshine on Long Lake

You can't get any closer to Long Lake! The Cabin at Sunshine is a few short steps to the sandy bottom of this crystal clear lake. The Cabin at Sunshine was recently remodeled to give the home a relaxed, lake feeling with unobstructed views of Long Lake. All new mattresses and appliances throughout the cabin. A new Webber grill is outside for those days when you want to spend every second outside. Walk into Naples for ice cream, cocktails, shopping, entertainment, boat rentals, and dinner.

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

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.

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!

Writers Cabin in the Woods with Sauna!

Nestled in the woods and on Adams Pond with new wood fired sauna! The cabin feels totally hidden away but is less than 10 minutes to Bridgton and Naples, hiking, beaches and restaurants. The woods are beautiful and peaceful and the pond is just down a mossy path. Great for couples or a weekend away. Large deck with grill and outdoor shower, firepit. There is a shared dock on the pond for swimming, fishing, or just enjoying the view as well as a canoe and 2 kayaks, and a paddle board.

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.

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. *** Remaining June Dates Have Been Discounted *** 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.

Cozy Lakefront Cabin-Private Dock-Kayaks-Firepit

Welcome to Salmon Point Cottage a 1,000 sq. ft. cabin on stunning Panther Pond. Deck sits less than 10’ from the water with direct dock access. Open concept living with high-end kitchen. Cozy up by the gas stove. Swim, kayak, or relax by the firepit—your private lakeside retreat awaits. This property has it all including: -Private Dock -Fire Pit -Complementary Kayaks -BBQ Grill -Gas burning fireplace -Washer & Dryer -Fully Equipped Kitchen

Romantic Pond Cabin | 65 Private Acres + Kayak

Escape to a Modern cabin on 65 acres, with a serene 25-acre pond. Feels secluded yet only half a mile from Route 302. • ✅ Dock & kayaks • ✅ Stone fire pit under the stars • ✅ Wildlife & beautiful views • ✅ 8 minutes to grocery store and restaurants • ✅ 1 mile of trail and access to a beaver dam • ✅ 2.5 miles to Sebago Lake state park - 45 minutes to Portland Book your escape today!