Family-friendly holiday rentals in Orr's Island

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

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.

Spacious & Sunny 1BR | Near Bowdoin + Route 1/295

Welcome to your Brunswick getaway! Our bright and airy 1-bedroom apartment is tucked in a quiet neighborhood just one mile from Bowdoin College, with fast, easy access to Route 1 and I-295. Surrounded by greenery, trees, and fresh Maine air, this is the perfect spot to relax, recharge, and still be minutes from everything Brunswick has to offer. Proximity to Freeport outlets, Bowdoin College, and spring hiking/coastal walks. Downtown Brunswick restaurants (great for Valentine’s dinners).

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled peacefully in a private clearing in the woods. Explore island beaches and hidden trails. This yurt is “glampy” inside with leather chairs and a substantial log bed. The yurt has a rusticator kitchen with all of the basics for cooking, small fridge, stovetop, sink. Water. Outdoor fire pit. WiFi . Check ferry options on Casco Bay Lines or Chebeague Transportation. Host will provide transport to/from ferry to the yurt.

Cozy log cabin on private pond, near Reid St Park!

Winter or summer, the Little River Retreat will help you step away from the world - but still be minutes from Reid State Park, Five Islands Lobster, the Georgetown General Store, and the rugged beauty of Midcoast Maine. This is our family camp, with our own books, games, and “vibe”. It is not a hotel, and some things may not be “industry standard”. We love the unique charm of this space and place, and many repeat guests do too. We hope you will treasure (and care for it) as we do!

Sweet Fern Cabin on Merrymeeting Bay

Nestled in the woods on 2.5 waterfront acres where the Muddy River meets Merrymeeting Bay. The cabin is 350 square feet of simple living with a panoramic view. There is a three season hot water outdoor shower and wood burning stove with plenty of wood included. Kitchen is fully stocked with cooking supplies and has off grid cold water sink. Outbuilding with composting toilet is right out the back door. Kayaks and stand up paddle board are available to rent for an additional fee.

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 Tree Dwelling 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!).

Modern Brunswick Tiny Home near Bowdoin & Downtown

A lofted bed space with additional optional pull out couch fitted with ergonomic foam mattresses. This space has air conditioning as well as heat and amazing natural light. Brand new bathroom with rain shower head! A full kitchen with mini fridge, separate freezer space, oven, stove and coffee/tea supplies. Centrally located in Brunswick, and quiet! Right across from Bowdoin’s Whittier Field, and 10 minute walk to Maine Street.