Waterfront vacation rentals in Chebeague 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.

Amazing Bay View Home with Hot Tub

This enchanting 2-bedroom home is a coastal dream come true! Luxurious and well-appointed, Casco Bay House sleeps up to six, provides a five-star stay, offers all of the comforts of home AND a relaxing hot tub spa. With stunning views of the water, the house also has easy access to dining, shopping, and sightseeing in Portland's lively Old Port district (just 5 minutes away). Whether you seek quiet tranquility or want to hit the town, this waterside house is the perfect home away from home!

Luxury Year-round Treehouse with private hot tub

The Canopy 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.

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.

Classic, calm river view & centrally located home

We are happy to share with you our coastal, colonial home set on eight acres along the Kennebunk River. Enjoy our quaint, warm home just 5 min to the beach and 3 minutes to Cape Arundel Golf Club. Our 4 bdrm, 2.5 bathroom suits short or long term stays. The location is ideal: 6 min from Kennebunkport, 15 min from Biddeford, and 30 min from Portland or Portsmouth! We hope to make you feel at home with the morning birds chirping and the calmness of the river just in back of the property.

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!

Higgins Beach *New* Beach Home & Private Offices

Custom designed contemporary at the beach. Perfect for a relaxing getaway, visiting family and friends or working remotely. Chef's kitchen w/ high end appliances, granite countertops, enclosed porch grill area. 3 bedrooms and 2 private offices Huge windows and amazing views from all of the rooms highlight the natural beauty of high tides, sun rises and sun sets. Wonderful beachfront walks and beautiful surroundings inside and out. Easy proximity to Portland's Old Port.

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.

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.

Wren Cabin + Wood fired Sauna

We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.

Garrison Cove Studio

Rare, Portland waterfront studio located in the heart of the historic Stroudwater neighborhood, awaits one or two guests looking for an urban hideaway. The studio occupies a 150 year old post and beam barn situated on the banks of the Stroudwater and Fore Rivers. Enjoy morning coffee on the river swing, meditate to the soothing sound of the nearby waterfall or linger over your favorite beverage in one of our comfy Adirondacks.

Stone Isle. 8 acres next 2 little john preserve.

Nestled on 8 acres overlooking Casco Bay, the Stone Isle guest house has 2 bedrooms, 1 bathroom and amazing water views. The guest house includes an open plan layout with a full kitchen, living room (with sleeper sofa) and a dining table for 4. Last but not least the guest house is a 5-minute walk from a 23-acre preserve that has numerous scenic viewpoints, tide pools and ledges, and picnic tables. Coastal Maine at its best!