Family-friendly vacation rentals in Peaks Island

Romantic A-Frame cabin in the woods

Stay at Hidden Pines Cabins. Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

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.

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled 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: fridge, stovetop, sink, water, firepit & firewood. Outdoor shower. WiFi . Cozy heater for cool spring nights. Ferry options on Casco Bay Lines or CTC Ferry. Host provides transport to/from ferry to the yurt.

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.

Cozy, Rustic Cabin on a Small Organic Farm

This little cabin in the woods is a wonderful place to get away from it all. Tucked away in a back meadow of our farm, hidden in the trees, you’ll love the cozy bed in the loft and privacy. It is a rustic, comfortable experience. No running water or electricity; we supply plenty of water and battery powered lanterns for you. The outhouse is close to the cabin, an outdoor shower near the farmhouse. Fresh organic sheets, wool blankets and linen down comforter make for a great sleeping place

Pristine Waterfront Studio Apt. Retreat

Studio apt. on the water where Casco Bay meets the Presumpscot River. Downtown Portland 2 minutes away. Perfect to... *Relax & enjoy the sunset & water views from decks *Head into Portland-Bon Appetite 2018 Restaurant City of the Year & "The Best Lobster Roles in Maine" *CNN named Portland as "one of the best towns to visit in 2024" *Drive up the coast, explore the beautiful beaches, lighthouses, quaint towns *Adventure inland for amazing hikes & mountainous views *Awesome music scene!

Crow’s Nest Tiny House at Old Crow Ranch

The Crow's Nest Tiny House sits nestled on Old Crow Ranch, a 70-acre working livestock farm, a true example of thriving Maine farmland. You'll be surrounded by fields and pine woods in Durham, Maine. Just outside Freeport and only 30 minutes from Portland, this cozy space makes a calming retreat away from the city - for a night or for a week. Fall asleep listening to the peepers and gazing at the stars, drink your morning coffee while looking out at the cattle grazing in the fields.

Peaks Island Master Bedroom Suite

Enjoy your stay at this conveniently located, light-filled, modern, chic living space--only a 4-minute walk from ferry, great sunsets, close to market and restaurants with a private entrance and deck. Walking distance to the best island beaches. Located on a quiet, dead end road off the main street. The space is found at the rear of one of Peaks Island's most beautiful, original Cape homes. Guests can enjoy a comfy queen size bed, organic cotton sheets, and a pull-out sofa bed.

Hope Cottage: Peaceful and Quiet Island Getaway

*Quiet and Peaceful *Easy Portland Access *Sparkling Bathroom Remote Downeast island experience just two hours from Boston ... Renovated home in the tranquil Tolman Heights section of Peaks (the island’s highest point) offers a modern kitchen and sparkling new bathroom. Sleeps 6-plus comfortably in bedrooms all equipped with ceiling fans. Spacious home is a short stroll to the Back Shore, with its dramatic views of Casco Bay and the open ocean. STHR-007313-2025

The Garden Cabin Tiny Home

Curious about tiny homes? Love dogs, gardens, pine trees, campfires, and birds? Hate cleaning fees? Our private 128 sqft cozy cabin is for you! On the spectrum between camping and a hotel room, it's a chill place to call home while visiting Portland. Enjoy our garden while sipping a beverage from your own deck or around the campfire. Heat and A/C in the cabin. Please, no smokers, kids under 7, or guest pets. STHR-000718-2018

Stunning Ocean Views From This Peaks Island Home

Completely remodeled classic Peaks Island home with stunning Atlantic Ocean white water views. Welcome to the newly renovated Valhalla on Peaks. This classic home underwent a complete renovation for your family's enjoyment. From the minute you step onto the property, your senses will be overwhelmed by the views, ocean breeze, salty smell, and the property's nostalgic feel.

Tiny Cottage Hideaway, close to everything

A studio built in 1920 turned one-bedroom Guest Cottage, full of charm, on Peaks Island. Within 5 minutes walking distance to the ferry, restaurants, beaches and "Down Front" shops. Perfect for 1-2 people and possibly a third. The 500 square foot Cottage is an off-the-beaten-path Maine experience. Peaks Island is an 18 min ferry ride from Portland.