Holiday rentals in Dingley Island

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Top-rated holiday rentals in Dingley Island

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Top guest favourite
Cabin in Norway
5 out of 5 average rating, 94 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.

Top guest favourite
The image captures an aerial view of a serene landscape with lush green trees surrounding calm waters. The shoreline curves gently, leading to a private dock that extends into the water. A soft sunset glow reflects off the surface, creating a peaceful ambiance.
Home in Georgetown
4.99 out of 5 average rating, 127 reviews

Moss House: A Modern Waterfront Cabin in the Woods

Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

Top guest favourite
A private hot tub is surrounded by trees displaying vibrant autumn leaves, with a gentle stream flowing nearby. A fire pit sits beside the hot tub, offering a cozy gathering space. The cabin's exterior features wooden siding and large windows that invite natural light.
Tiny home in Norway
4.94 out of 5 average rating, 256 reviews

Glass Wall Waterfront Hot Tub Fireplace Tiny Home

Wake up to rushing waterfalls right outside your glass wall in this romantic waterfront tiny home in Norway, Maine! Private hot tub with river views, see-through gas fireplace, cozy raised queen bed overlooking the water, outdoor shower, hammocks, and direct access to hiking trails. Total privacy—no neighbors in sight. Modern kitchen, heated floors, fast WiFi, and thoughtful touches for couples or solo escapes. Romantic getaway near Sunday River skiing, golf & Maine adventures. Nature's oasis

Guest favourite
A private deck overlooking the water features a round table with four surrounding chairs, sheltered by a large umbrella. The scene includes lush trees lining the opposite shore, with clear blue skies reflecting on the calm water.
Cottage in Harpswell
4.92 out of 5 average rating, 142 reviews

Seal Ledge - water's edge cottage with kayaks

Beautiful cottage sitting literally on the water's edge makes you feel like you're staying on a boat (minus the rocking!). Soak up the sun and watch the sun set on the private deck or take a few steps down to the dock and use our kayaks to go visit the seals that hang out on the rocks just down the cove all summer long. The cathedral ceiling great room is all glass facing the water so you can enjoy if it's too cool to sit outside. Only 15 mins to Brunswick and central to everything Harpswell!

Top guest favourite
Flat in Phippsburg
4.88 out of 5 average rating, 16 reviews

Beautiful Waterview Special Sunsets

Take it easy at this unique and tranquil getaway. Beautiful private property on the New Meadows River with a dock for fishing, swimming and Kayaking. Walk out your door and you have a nature preserve with 1800 acres to bike, hike and bird watch. Minutes to beaches and golfing and centrally located to exploring the Great State of Maine. Enjoy the sunsets from your private deck as you unwind from eating lots of Lobsters....The fire pit is always available along with Marshmallows to toast.

Top guest favourite
The exterior of the A-frame cabin is showcased, featuring a unique wooden facade and metal roof. Sunlight streams through tall triangular windows, illuminating the surrounding wooded area. A gravel path leads to the entryway, enhancing the cabin's connection to nature.
Cabin in Freeport
5 out of 5 average rating, 133 reviews

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

Top guest favourite
Cabin in Georgetown
5 out of 5 average rating, 198 reviews

Near Beach+Cedar Sauna+Outdoor Shower+Pond+FirePit

Unwind at your own studio cabin with forest views, private sauna & pond! * New Private Cedar & Glass Barrel Sauna * Minutes to Reid State Park Beach & 5 Island🦞 * Fire Pit * Outdoor Shower * Rain Shower & Heated Bathroom Floor * AC/Heat * TV & Record Player w/Vinyl * Fast Wifi *Spruce Studio is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart & separated by a privacy screen and natural landscaping.

Top guest favourite
A spacious two-story home is shown with a welcoming front porch adorned with rocking chairs. Solar panels are visible on the roof, which is complemented by several skylights. Surrounding greenery enhances the peaceful setting under a partly cloudy sky.
Flat in Harpswell
4.93 out of 5 average rating, 223 reviews

Comfortable studio apartment in quiet location

Peaceful, rural second story studio apartment. Near Middle Bay in beautiful Harpswell, Maine. Enjoy our farmer's porch or walks to the shore deck to look out over the water and enjoy a sunset or go the the shore for a swim in summer. Short distance to Brunswick and Bowdoin College, local restaurants. The host also teaches porcelain doll making. You could learn to make porcelain dolls while enjoying the Maine coast.

Top guest favourite
A bright living area is captured with hardwood flooring and a high tongue-and-groove ceiling. A plush sofa sits opposite a small coffee table, with shelves displaying books nearby. Windows frame the space, allowing natural light to illuminate the area.
Guest house in West Bath
5 out of 5 average rating, 56 reviews

Spruce Ledge Boathouse

Oceanfront escape! Perched over the New Meadows river this western facing, private, one bedroom cabin includes full kitchen, outdoor BBQ & dining area, gas fireplace, full bathroom, & deep water dock access. Watch the Osprey, Bald Eagles, lobsterman hauling traps, and the many sloops and yawls that traverse the saltwater river. Outdoor stairs (75 or 5 flights of stairs in photos) are required to access cabin.

Top guest favourite
The cottage exterior features light-colored siding and a distinctive steeply pitched roof with a prominent window above the entrance. Double doors framed by a large glass panel invite visitors inside, surrounded by lush greenery and flowering shrubs.
Guest house in Boothbay Harbor
5 out of 5 average rating, 267 reviews

The Sparrow’s Nest Charming Country Cottage

The Sparrow's Nest is located on a country road approximately 5 miles from downtown Boothbay Harbor. The Sheepscot River, it's coves and nature trails are close by. Enjoy the beautiful country surroundings, gardens, and the miracle of nature. What a delight to wake up to the sound of birdsong while enjoying a cup of local coffee, or sitting by the outdoor fire sipping wine and taking in the beautiful night sky.

Top guest favourite
A spacious waterfront view captures the serene Kennebec River, adorned with small islands and surrounded by lush green trees. The sky is bright blue with scattered clouds, reflecting a tranquil natural setting.
Guest house in Bath
5 out of 5 average rating, 176 reviews

Waterfront Sunrise Cove Cottage

Unwind with spectacular sunrises from this sunny waterfront cottage on a tidal cove in the Kennebec River! This is the perfect home base for a midcoast Maine getaway. The post-and-beam cottage has cozy furnishings and expansive views across a field, pond, and cove. Bald eagles and osprey soar overhead, sturgeon leap in the river & nights are full of stars. Owners live on property with small dog.

Guest favourite
An aerial view captures a serene point surrounded by calm water, with lush green trees lining the rocky shore. The rocky outcrop extends into the water, providing direct access to the tidal area. The tranquil setting highlights the natural beauty of the landscape.
Cottage in Harpswell
4.89 out of 5 average rating, 128 reviews

Rising Tide Times - quintessential Maine cottage

Classic Maine cottage on the end of a point, surrounded by water on 3 sides provides stunning views. The perfect backdrop for the quintessential cottage vacation. Features spacious decks, direct tidal access for kayaking, and outdoor firepit. 15 min to downtown Brunswick/45 min to Portland. We even have Kayaks onsite for guests to paddle around Cards Cove. Perfect for couples and families!

Popular amenities for Dingley Island holiday rentals

  1. Airbnb
  2. United States
  3. Maine
  4. Cumberland County
  5. Harpswell
  6. Dingley Island