Smoking friendly holiday rentals in Cumberland County

The Redbird Retreat

Quintessential Maine cabin on Bonny Eagle Pond! Come relax in this private, cozy cabin in beautiful Southern Maine. The cabin boasts private access to a 211-acre quiet body of water w/ a dock, along with kayaks, paddle boards, floats, seating and tables and more! The large yard offers two fire pits, yard games, outdoor dining and cooking. The cabin offers an enclosed porch, indoor dining, a full kitchen, a workspace with free Wi-Fi, and comfortable beds and is nestled in on a small private road.

Black Point Surf Club

Black Point Surf Club is within 2 miles of 3 very popular beaches, and more. You will have the benefit of an included beach pass to Scarborough beach where you can Surf all day. Enjoy being set apart from the hustle and bustle of the a beachfront rental but close enough to enjoy it thoroughly. When the Surf is flat you are 20 minutes to Portland and Old Orchard Beach. You can also use the knowledge of your host for the best restaurants, bars, and ways to set sail through your Maine vacation.

Maine A-Frame with Hot Tub, Game Room, Lake Access

Escape the city and relax at Camp Merryweather. Our A-Frame is perfect for a romantic getaway or a family retreat with the kids and dogs welcome! If you’re a work from home professional looking to escape your normal routine, we’ve got you covered! With a fully equipped work space and reliable high speed internet you can break free from the pressures of the city while still staying connected. Enjoy our hot tub and game room Come experience our slice of heaven for yourself, you won’t regret it!

Portland, Beaches & More! Fenced Yard for Dogs

Conveniently close to lots of beaches - just minutes to Portland, OOB, parks, trails & more! Clean and pet friendly! Large private fenced in backyard with patio & firepit Updated kitchen & spacious counter top perfect for cooking, entertaining (dishwasher, garbage disposal, stove w/ air fry, microwave, full fridge/freezer) King bed in Lighthouse room Queen bed in Evergreen room Big comfy sectional with daybed - cozy space to gather, play games or just relax in front of the bigscreen!

Apartment on Boody St - fenced yard, pet friendly!

Stay in our unique garage apartment less than three blocks from Bowdoin College & within walking distance of downtown Brunswick! Convenient & cozy, this studio apartment has what you need to get away and yet still be in town. Fast internet & a dedicated work space make this a functional, fun, central location for your adventures in the Midcoast region. A short drive to Harpswell or Freeport & within walking distance of dozens of shops & restaurants. One bedroom with a loft. Shower is small!

On the water Boathouse!

In the water! Two story boathouse. Originally built in 1939 and parked boats in until 1972. Converted to living space in the early eighties. The upstairs consist of a bedroom walk in closet and a balcony. The downstairs is a living room, kitchen and bathroom. Walk out the door to the patio , dock , and beach! You won't find anything closer to the water! The balcony is the perfect place to watch the sunset, thunderstorms, or sip your morning coffee. Watch the fish out the window!

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!

Rustic, cozy cabin on Sebago Lake. A hidden gem.

Step out of the screened in patio to lakeside relaxation. Dive into crystal waters, snorkel or float with a cool beverage. Kayak or canoe out to Turtle Cove and enjoy the wildlife in this natural waterway teeming with birds to include our resident Blue Heron, ducks, geese, and loons who make this place their home. We have the fortune of bald eagles in several tall pines. Turtles sunning on doting rocks and lily pads in bloom greet us each day. It is a natural water landscape.

Downtown Crash & Snooze — 2 Rooms, Sleeps 7

Previously recognized as a Superhost, I’ve proudly welcomed many satisfied guests. When the neighborhood experienced changes due to years of loud construction and increased homelessness, I received some negative reviews. I assure you, My property is a clean, comfortable, and thoughtfully maintained retreat. Guests will appreciate a private entrance, two bedroom stay with on-site parking that's walking distance to everything Portland has to offer.

Top of the Old Port-1 BR APT

The unit is cozy and quiet tucked at the rear of the building on the first floor. There are privacy/light block shades for your convenience. There’s a bit of an Egyptian theme in the apartment now but it will always be changing. I like to promote friends’ art work and I will always have live plants to keep the air fresh. Pet fee is per pet per stay. ***We’ve recently upgraded our pest control measures to ensure the highest level of cleanliness.***

Blueberry Hill

Beautiful property located on Watchic Lake in Standish Maine. Clear clean spring fed lake. 25 minutes to Portland with access to shopping, restaurants and entertainment. 45 minutes to North Conway New Hampshire. Where you wil find plenty of shopping, restaurants and winter skiing. Property includes use of Main Chalet home year round and two additional cabins each sleeping 4 are available from May-Oct. Great for extended families and friends.

The Maine Escape

Tucked into the trees and just a short walk from downtown Westbrook, The Maine Escape is your calm and cozy home base for all things Maine. Only 10 miles from beaches, Sebago Lake, winding rivers, and downtown Portland, this modern 2BR retreat blends natural beauty with unbeatable access. Whether you’re exploring the coast or staying in, The Maine Escape is your perfect adventure post in Maine.