Pet-friendly holiday rentals in Freeport

Luxury Year-round Treehouse with private hot tub

Cliff House 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.

Freeport Village Sunny Studio

Privacy and nature on the edge of the Village with a deck onto the yard, laundry, and small kitchen. You'll enjoy sitting out on the deck listening to the birds and you may see a deer, woodchuck, or chipmunk. Very quiet residential street. Walk to trails (5 min, Bow Street Market (5 min), LLBean (5min), restaurants (5-8min), and Amtrak (4min). Have the best of both worlds! We have an extensive guidebook to the area available through the Airbnb platform. Take a look! (Note: No microwave.)

Charming Historic Freeport House

Bring the whole family to this historic house just minutes from downtown Freeport and the LL Bean flagship stores. The cozy central kitchen and dining are flanked by two separate living rooms making plenty of room for fun and relaxation! With two twin beds, toddler bed and full-sized crib we can accomodate any family. Catch glimpses of the Harraseeket River from this updated 1840s home on a half acre. A wonderful jumping off point for both Portland and the natural beauty of Mid-coast Maine!

Waterfront, 5 Bedroom, Spacious Home in Freeport

Large, luxury 5 bedroom home on Harraseeket Cove & South Freeport Harbor, great for kayaking & wildlife, set on 3.5 acres tucked away in the woods! WiFi, Smart TVs, backyard grills, firepit, outdoor furniture and kayaks. Waterfront tranquility just 3 minutes to Freeport's lively downtown shops, restaurants, breweries, and LLBean. Wolfes Neck State Park's stunning coastal trails and forests are close by and Portland's scenic Old Port is 20 minutes! Enjoy an authentic coastal Maine experience!

Waterfront Sunrise Cove Cottage

Unwind with spectacular sunrises from this sunny waterfront cottage on a tidal cove in the Kennebec River! This is the perfect home base for a midcoast Maine getaway. The post-and-beam cottage has cozy furnishings and expansive views across a field, pond, and cove. Bald eagles and osprey soar overhead, sturgeon leap in the river & nights are full of stars. Not recommended for those with mobility issues. Bathroom is downstairs, bedroom is upstairs. Owners live on property with small dog.

Cozy & Private Studio Apartment

Recently renovated studio apartment, very cozy, with a private side yard and entrance, kitchenette and TV (Roku with Netflix, Disney Plus, Hulu and Amazon). Very comfortable queen size bed with floor space for kids, if desired. Fantastically located just over a mile from beautiful Winslow Park's walking trails and beach, four miles south of downtown Freeport's shopping and 15 miles north of the popular city of Portland. Housebroken and well behaved pets welcome to join their humans!

StreamSide Getaway- HOT TUB / AC/ Wi-Fi

The Streamside Getaway offers a luxurious glamping experience in a new solar and wind-powered Geodome. Equipped with custom furniture, new hot tub,luxury appliances, free high speed wifi, AC/Heat Unit and modern bathroom and kitchen facilities, guests can enjoy a homely and comfortable stay in nature. A glamping site built in 2022 offers a contactless check-in process with a custom key code. Additionally, we have added archery, axe throwing, and kayaks to enhance your outdoor activity!

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!

Fully Updated Airy Historic Home in South Freeport

Conveniently located 5 minutes from downtown Freeport, 20 minutes from Portland Jetport, and 20 minutes from downtown Portland. This newly renovated, charming, and sunny 200 year old home is perfect for your Maine getaway. It is a fantastic home-base for exploring Southern and Midcoastal Maine while enjoying close proximity to shopping in Freeport and Portland's award-winning restaurants and attractions as well as beautiful beaches, islands, museums, lighthouses, and much more.

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.

Studio Apartment in Freeport

Relax with your family in this modern studio apartment. Kids or adventurous adults will love climbing into the twin bed nook to read a book or sleep. Have a seat at the table to play a board game, eat a home cooked meal, or devour takeout. Lay in the king bed or sit on the couch to watch a movie or just relax. We are in a private wooded area just 5 minutes from downtown Freeport.