Holiday rentals with a fire pit in Winslow

Lakefront Log Cabin on Pleasant Lake

Best view on the Lake! 500' of frontage out on a point. Private boat launch and dock site available. Covered deck to watch the sunset. Outdoor firepit, as well as indoor gas insert. Propane grill on site. Plenty of parking available. In the winter, ideal location for snowmobiling and ice-fishing. Right on to the lake and then 4 locations to get on local/ITS trails. Great fishing 200’ from the porch. Once the ice is out, hit the black crappie and Smallies from the convenience of a private launch

Scenic Lake & Urban Conveniences

Charming lakeside working retreat or family getaway! Nestled in a tranquil cove, this cozy 3-bedroom home offers a balance of relaxation and adventure. Enjoy kayaking, fishing, or unwinding by the fire pit. The house features a fully stocked kitchen for family meals, a basement theater for movie nights, and a bonus room perfect for games or remote working. Minutes from amenities and hiking trails, and wildlife parks. Embrace the best of nature & comfort in our scenic, family-friendly lakehouse!

the Anthracite at Crie Hill

Kick back and relax in this calm, stylish off-grid retreat. Set high on a hillside looking across the valley with a great view of the opposing ridge, this new luxury cabin was designed with relaxation and privacy in mind. Bask in the outdoor tub during cool mornings and watch the fog rise off the river valley below, or enjoy a fire in the sunken granite pit while you barbeque. Eco-conscious guests will appreciate the solar power setup with a clean propane standby generator for cloudy spells.

Peaceful Lakeside Getaway with Hot Tub!

Enjoy our fully renovated, lakeside, four season retreat. During the summer spend time fishing, kayaking, swimming, lounging in the hammock and then escape the heat inside the fully air conditioned house! In any season, unwind in the lakeside hot tub, take in every gorgeous sunset and dark starry night or gather around the campfire. The winter months bring snow shoeing, ice fishing, snuggling up in the living room playing games or watching a movie fireside. There is something for everyone!

Tree Yurt

The Tree Yurt is quite literally a yurt in the trees. Surrounded by nature, this is YEAR ROUND glamping close to Portland. Water for the outdoor shower and outdoor sink is seasonal Typically May through October. We do provide water for colder months. A main house sits closer to the driveway and There is a chance the house and the yurt will be rented out at the same time. The yurt is about 200 feet from the house and the only shared space is the driveway, so it is actually very private :)

Renovated home with amazing waterfront views

Welcome to Dancing Pines Cottage! We are located across from West Harbor Pond with beautiful water views in each room. Relax on the deck or bbq on the patio or take a short drive into charming Boothbay Harbor town for lobster rolls. We have three bedrooms and a den/office and 2 full bathrooms and can accommodate up to 7 guests. The house is private and has ample parking. One week rentals for June, July, and August (Saturday-Saturday). Starting January 2025 we will no longer allow pets.

Freeport Escape -Downtown, Fire-pit, 3 Kings + AC

The Freeport Escape Built in the early 1900s, this home has the old charm yet all the modern amenities you could think of. Come stay directly in the heart of Freeport, walkable to all the shopping, restaurants, breweries, and Amtrak station located in town. This corner lot provides privacy and is the perfect place to enjoy warm summer nights by the fire-pit, grilling out on the porch. We got you covered to enjoy the beautiful Maine fall and winter by the fireplace inside. STRR-2022-82

Terrapin Station @ Porter Lake – Lakefront Living

Several acres directly on a secluded portion of Porter Lake so you can bring your boat or enjoy the local trails with your ATV in the summer. Enjoy ice fishing, snowmobiling and snowshoeing in the winter. This 1500 square foot cabin offers all the modern conveniences. Close to area hiking and mountain climbing in summer and Sugarloaf and Saddleback skiing in winter. Awesome colors of foliage changes during the fall. Optional hookup for motorhome and plenty of space for tenting.

Cub Cabin- a Peaceful Paradise at Fox Carlton Pond

Welcome to Fox Carlton Pond! Settle into our Cub Cabin surrounded by the beauty of nature at a peaceful resort on our 5 acre private pond alongside the Sandy River. Our Cub Cabin is furnished with a bunk bed (see photos) with a double mattress on the bottom bunk that sleeps 2 and a single mattress on top bunk that sleeps 1. Enjoy walking trails, lawn games, fire pit, pickle ball, use of canoes, kayaks, peddle boat and docks for exploring, fishing and swimming.