Pet-friendly vacation rentals in Bailey Island

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.

Cozy Private Lux Yurt W/Mt View/HOT TUB /AC/WiFi

Birdsong yurt is a truly unique and special lodging experience you won’t forget. An ideal couple’s getaway or perfect place for friends and family to relax and connect with loved ones. Located on two private acres of land surrounded by trees, you will feel close to nature while still having the comforts of modern conveniences. The deck is the perfect place to enjoy the Mountain View, watch the sunsets and stargaze with a glass of wine by the gas fireplace! Relax in the Hot Tub to end the day!

Waterfront Private Apartment only 5 min to LLBean!

Guest apartment with private entrances, king bed, pull out sofa, kitchenette, walk-in shower, and porch facing the water providing the perfect relaxing coastal Maine experience! Custom built home on 8 acres tucked away in the woods with waterfront access to Harraseeket Cove & South Freeport Harbor, great for kayaking! Located 5 minutes from LL Bean and Freeport's many shops, restaurants, bars, etc. Wolfes Neck State Park and its stunning coastal trails and forests are less than a mile away.

Floating Island Cabin Private Pet-Friendly Retreat

Waves peacefully lapping at your cabin door... Watch the sunrise over the lake from your comfy bed. Cook your favorite meals. Chill out in a hammock. Bask in the campfire glow. Dine on the floating front porch. Enjoy hot showers. Play on the rope swing. Tie a canoe up next to the porch. Explore the trails of a 14 acre wooded island. Enjoy super clean, Superhost, Maine Guide hospitality. We'll help you settle into the rhythm of island life and return you refreshed, renewed, and inspired.

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.

Gorgeous Studio on the Kennebec

Gorgeous riverside studio, the smaller of two AirBnB houses on the same property on the outskirts of beautiful and historic Bath, Maine. (The other, “Beautiful Summer River Retreat,” is a separate Airbnb rental.) Kitchenette, bathroom/shower, living room, and bedroom. Simple, modern decor. Close to great shops, restaurants, and beaches, and just a 20-minute drive from Bowdoin College. Adjacent to a boat launch, and a short walk from the Bath Marine Museum and a scenic dog park.

Charming Cottage With Spectacular Water View

Find peace and serenity as you gaze at the glistening waters of the Sheepscot River. Our property sitting on Davis Island in Edgecomb, Maine overlooks the quaint town of Wiscasset, providing a calm atmosphere, stunning evening sunsets, and panoramic views. Located within the Sheepscot Harbour Village Resort, you are in a prime location to have access to local shops, antique markets, and restaurants. Take a stroll down to the Pier where you can experience the water up close.

SNOW SWEET, A Yurt for All Seasons

Snow Sweet at The Appleton Retreat is very private, check out the Trail Map. This contemporary yurt faces the Field of Dreams and has a nice view of Appleton Ridge. It features a private therapeutic hot tub on the deck, a fire pit, and fast wifi. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.