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Holiday rentals in Ring Island

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Top-rated holiday rentals in Ring Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A modern structure designed with a staircase leading to a rooftop deck is surrounded by trees. Two wooden Adirondack chairs are positioned near a fire pit, offering a cozy outdoor gathering space. Gravel paths and natural greenery enhance the overall setting.
Shipping container in Casco
4.89 out of 5 average rating, 19 reviews

Point Sebago Resort - Star Gazer (Single)

Point Sebago's Stargazer is truly 'Glamping' - also knows as glamorous camping in style - it captures the glam by bridging the outdoors with memorable luxury. This is most certainly camping without the 'roughing' part. It has been designed for that more luxurious experience. It is fully furnished with a double bed, and a single pull out, linens, pillows and blankets, a coffee maker, coffee mugs, microwave, small refrigerator, and a sink. Each unit will have heat, air conditioner and a bathroom.

Guest favourite
A beautifully crafted treehouse is illuminated at night, highlighting its wooden exterior and spiral staircase. Soft lights strung in the surrounding trees create a warm ambiance, inviting serenity and connection with nature.
Treehouse in Sanford
4.96 out of 5 average rating, 252 reviews

Luxury Year-round Treehouse with private hot tub

Cliff House 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.

Guest favourite
A welcoming approach to a charming waterfront home is presented, featuring a wooden staircase leading to a spacious deck. Lush greenery surrounds the pathway, with sunlight filtering through the trees, creating a bright and serene atmosphere. A lamp post adds a touch of elegance to the outdoor space.
Home in Casco
4.91 out of 5 average rating, 11 reviews

Sebago Waterfront with beach, kayaks, + amenities

Escape to this charming waterfront home on Sebago Lake and enjoy the tranquility of Maine's Camp Life. The sandy beach and cove are perfect for swimming, kayaking, and fishing and the 2 decks and back yard are great for grilling dinner and taking in the views by the fire. With comfortable accommodations for up to 6 adults (or 8 guests with children), this cozy retreat offers everything you need for a memorable lakeside vacation! *Please note that bed sheets + towels are guests' responsibility.

Top guest favourite
Cabin in Norway
5 out of 5 average rating, 91 reviews

Modern Cabin: View, Hot Tub, 10 min Walk to Lake

Architect-designed alpine cabin with panoramic White Mountain views, including Mount Washington Relax in the hot tub, watch the sunset over the mountains, and enjoy a peaceful forest setting close to lakes, hiking trails, and skiing. 4WD or AWD REQUIRED Nov 1st-April 15th Starting May–Fall 2026, there may occasionally be (weekday only) construction noise up the road (250ft) from neighbors building their home. Work would occur roughly 8am–4/5pm and not every day. Cannot see it from the house.

Guest favourite
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.
Home in Casco
4.97 out of 5 average rating, 30 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!

Top guest favourite
The exterior of a post and beam cottage is shown, featuring a light wood facade and a brown shingled upper section. Two black Adirondack chairs are placed on a wooden deck, accompanied by potted plants. Large windows offer a view of the forested surroundings under a partly cloudy sky.
Cottage in Pownal
4.99 out of 5 average rating, 458 reviews

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.

Guest favourite
An aerial view showcases a serene lake surrounded by lush greenery, with several homes visible along the water’s edge. The dense wooded area offers a natural backdrop, while the calm water reflects the landscape. A red marker highlights the property location near the water.
Tiny home in Casco
4.95 out of 5 average rating, 20 reviews

Maine Glamping at the Lake with direct lake view!

Come try one of the best places to enjoy a real Maine Summer at the lake in our brand new 2024 Keystone Hideout loft destination-home, hooked up to power, private well water, and septic on site. Wifi and Netflix tv. Solar panels on the roof, stereo/dvd player, gas stove and oven, AC, Fireplace in master bedroom, screen house for outside dining, wood deck and Gas Grill. Boat ramp next to our property, also Thomas pond is home to several species of fish, fishing & swimming on site possible.

Guest favourite
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.
Home in Casco
4.95 out of 5 average rating, 20 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

Guest favourite
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.
Home in Casco
4.94 out of 5 average rating, 54 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.

Guest favourite
The cabin exterior is showcased with large glass walls, allowing natural light to fill the interior. A wooden deck is lined with outdoor lights, leading to a hot tub. Surrounded by trees, the peaceful setting is visible, creating a serene outdoor atmosphere.
Home in Naples
4.98 out of 5 average rating, 188 reviews

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!

Top guest favourite
A cozy interior features natural wood paneling and beams. Two upholstered chairs are positioned near a large window, allowing light to fill the space. A small bookshelf holds several books, while kitchenware is organized on a nearby shelf. A white stove complements the rustic setting.
Cabin in Bridgton
4.95 out of 5 average rating, 188 reviews

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.

Guest favourite
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
4.92 out of 5 average rating, 173 reviews

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.

Popular amenities for Ring Island holiday rentals

  1. Airbnb
  2. United States
  3. Maine
  4. Cumberland County
  5. Casco
  6. Ring Island