Chalet holiday rentals in Owls Head

Sunset Chalet | Lakefront • Hot Tub • Game Room

Tucked along the quiet shores of Belgrade Stream and Messalonskee Lake, Sunset Chalet is a cozy waterfront hideaway designed for connection, comfort, and joy. Whether you’re sipping morning coffee on the deck, unwinding in your private hot tub, or making memories in the game room downstairs, this is a place to slow down, breathe deeply, and just be. Built for couples, small families, or anyone seeking a four-season retreat, Sunset Chalet is where nature meets nostalgia—and every stay becomes a

Pristine, Peaceful Kingfield Chalet

Just a short 15-20 minute drive from Sugarloaf and 3 minutes from historic downtown Kingfield, this chalet provides a peaceful, private respite after a busy day on the mountain. Our 2BR, 1BA eco-friendly chalet is tucked back from the road, with distant neighbors and fast WiFi. You can be surrounded by nature but only minutes from lovely restaurants, local shops, grocery store, gas station and tons of trails, rivers & lakes for snowshoeing, XC, snowmobiling, hiking, huts, MTB, kayaking & more.

Cozy lakeside chalet

Immaculate, cozy and quaint lake side chalet with dock and beach on pristine George’s Pond. Enjoy beautiful sunrises and kayaking on the clean, clear water of the 360 acre pond known for its variety of fish. Comes fully furnished and equipped with all the normal amenities, including a gas grill, large fire pit, 4 kayaks, paddles and jackets to explore the lake. Only 23 miles to Acadia and Bar Harbor, and conveniently located 15 minutes to Ellsworth, and 5 minutes to a small trading post store.

Oceanfront Retreat 3 miles to Acadia National Park

A lovely 2 BR waterfront cottage near Bar Harbor that sleeps 6 is in a wonderful park-like, oceanfront location with a large lawn area and a spectacular wide, flat beach; Cole Cottage (and sister Cross Carriage House) are in a unique and beautiful place to really experience Mt. Desert Island's natural environment. The property is only three miles from the main entrance to Acadia National Park. (the 2 BR carriage house is optionally-available to rent. Together the two units sleep up to 10).

The Guzzle

Bring the whole family to this great place with lots of room for fun. With our chalet style house you will have plenty of space for entertaining. We are located on a dead end road perfect for walks with the family with breathtaking views of the sunset all summer. The hot tub located on the front porch is perfect for stargazing at night! The house is located 23 miles from Ellsworth, 10 miles from Winter Harbor which is home to the ferry terminal that will take you to Bar Harbor for the day!

Acadia area waterfront Chalet on 12 secluded acres

With unobstructed views of Flanders Bay and the islands and mountains beyond, our quaint Chalet sits nestled on 12 acres of unspoiled nature. The three bedroom, knotty pine, pet-friendly Chalet stands just 400 ft. from our beach; you’ll enjoy direct walking access to the Flanders Bay shoreline. Enjoy a scenic 40 minute drive to Acadia National Park and Bar Harbor or just kick back for a peaceful afternoon soaking in the views from the deck or exploring the natural surroundings.

The Hideaway

Welcome to our cozy 3-bedroom home, nestled in the heart of downtown Kingfield. This family-friendly retreat is perfect for relaxing while exploring all the area’s seasonal activities. Just an 18-minute drive to Sugarloaf Mountain, it’s ideal for skiers, snowboarders, and winter sports lovers. Not a skier? No worries! With plenty of driveway space for snowmobile trailers, you’ll enjoy direct access to the Interconnected Trail System (ITS) from the property.

Visit Beautiful Home on Snow Pond

Belgrade Lakes, Maine's premiere lakes region. Beautiful, four season home on 9 mile long, Messalonskee Lake also known as, Snow Pond. Come to experience life the way it should be. Sunrise view, from master bedroom and lakeside deck surrounded by undeveloped wooded shoreline. Swim, canoe and kayak from private dock. Loons, eagles, osprey, and beavers can be your neighbors for a relaxing week at the lake. Open concept kitchen dinning and living room.

Mainely Green Lake Superior Recreational Retreat

This gracious three bedroom two bathroom home is the perfect getaway to relax and experience Maine. Our home is located in a secluded area where you right away feel that you are entering a calm and peaceful place. We have tried to make our home as cozy and family friendly as possible. Cozy up by the fireplace and have a wonderful time. In the summer you can enjoy swimming in the lake, hiking, biking, fishing, outdoor bbq, outdoor fire pit and much more.