Vacation rentals in Dingley Island

Quaint & Peaceful Designer's Oceanfront Cottage

Coco Cottage is a peaceful, cliffside escape with stunning 180° views of Harpswell Sound. Located at the end of a private road, it’s perfect for a designer’s retreat or family getaway. Three bedrooms—two queens, plus a twin/office combo—make it ideal for remote work or rest. Relax fireside and watch a movie, dine on the patio, read on the dock, or explore the amazing trails, beaches, seafood and sunsets of Harpswell. Enjoy oceanfront tranquility just 15minutes from Bowdoin College and Brunswick.

Waterfront Farmhouse with Modern Flair!

On the shores of Winnegance Creek in Bath, Maine—one of America’s best small towns—this 19th-century farmhouse has been completely renovated. Boasting waterfront views and sitting on more than an acre of land, opportunities for recreation and relaxation abound. Enjoy the outdoor deck, fire up the grill, visit the beach or the farmers market, explore the area via kayak, stargaze—so much to do! Not to mention shopping, restaurants, and all that downtown Bath and midcoast Maine have to offer!

Sunset on the Shore

This secluded waterfront oasis offers the ultimate escape from the everyday. Set against a backdrop of serene waters, the property features a private dock for easy boating access and a tranquil place to unwind. Whether you're enjoying the water at sunrise or soaking in the vibrant colors of the sunset, every moment here feels like a peaceful retreat. With the perfect balance of privacy and nature, your waterfront oasis is an idyllic place to recharge and create lasting memories.

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!

Classic Maine Cottage - dock, sauna & kayaks

The Perfect Maine Cottage! On the edge of the ocean, carefully preserved with traditional details. Charming, open floor plan, with a wall of windows to the ocean. Sunny large wrap-around deck and screen porch creates beautiful outside spaces to enjoy. Perfect for listening to waves and watch lobstermen pull up their traps. Cathedral ceilings and Scandinavian design gives the cottage an exclusive feeling. Gentle stairs lead to the private deep water dock for all kinds of boating.

Modern Treehouse w/Water Views+Cedar Hot Tub

Stay in our custom designed tree dwelling w/ wood-fired cedar hot tub up among the trees! This unique structure is perched atop a 21-acre wooded hill sloping to water views. Enjoy stunning views from the King size bed through a wall of windows. Located in a classic coastal Maine village w/ Reid State Park's miles of beaches + famed Five Islands Lobster Co. (See 2 other tree dwellings on our 21 acre property listed on AirBnb as "Tree Dwelling w/Water Views." See our reviews!).

Tranquility Redefined. The Maine House on Dingley

Available Nov. 1- April 28- 7 Beds - Sleeps 10 Tucked along the rocky coast of Harpswell’s Dingley Island, The Maine House blends comfort with understated seaside elegance. Enjoy sweeping ocean views, then unwind by one of two fireplaces after a day of ice skating or soaking in the hot tub beneath a starlit sky. A chef’s kitchen sets the stage for shared meals, while the pool table, private office, and exercise equipment ensure a cozy, well-rounded winter retreat.

Perched atop the Coast of the Atlantic Ocean

Enjoy sweeping vistas of the Atlantic Ocean from this 2002 home perched among spruce trees above the rocky coast. Watch for bald eagles and seals. Fall asleep to the sound of crashing waves. Walk down to the edge of the ocean to lounge or picnic. Walk 6 minutes or drive the 0.1 miles to the park entrance. Hike the Little River Trail. The house has vaulted ceilings, panoramic views, fully equipped kitchen, and whirlpool bath.

Waterfront Cottage On Basin Cove - Amazing Sunsets

Bright, airy cottage right on Basin Cove,a tidal cove in Harpswell Maine. Cool breezes with pristine views, especially for the sunsets over the cove. At the end of Harpswell Neck, so it feels like you're far away, but still only an hour from Portland, 1/2 hour from Freeport & 15 minutes from Brunswick. Use it as your hub to explore Midcoast Maine or hunker down and enjoy the screened in porch after a swim in the cove.

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.

Maine Coast Waterfront Retreat

Welcome to your dream coastal escape in pristine midcoast Maine! This 3,200-sq-ft waterfront home offers 150 ft of shoreline, a private deepwater dock, and a furnished deck with sweeping views. Inside, enjoy vaulted ceilings, skylights, a stone fireplace, and a chef’s kitchen with island. The upstairs game room and six beautifully appointed bedrooms provide plenty of space for family and friends.

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!