Smoking friendly holiday rentals in Cumberland County

LUX Designer Private Waterfront

Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

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.

A delightful historic Barn* Unique / Salt Hot Tub!

"The Harmony Barn”.We converted 1/2 of our barn into a queen bedroom, living room, kitchenette & giant walk-in shower. You will also have your own outdoor Salt water Hot Tub! Our antique house is on 4 acres of land. We are minutes from Portland & the ocean, but you will feel like you are in the middle of nowhere. We live across the street from 125 acres of nature trails. If you have a pet with a loud voice! Have no fear! No one will hear a thing! Including us! Bricks are great insulation!)

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!

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. I have a very eclectic and unique style that many people enjoy. 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*** Reservation form is incorrect. If you are bringing two pets the fee is $200**

Beaches, Portland & more! Coastal Getaway w/ pets!

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!

Tri-Lake Escape: Brandy Pond

Tri-Lake Escape offers the ultimate waterfront getaway with direct access to Brandy Pond, Long Lake, and Sebago Lake. This charming retreat is perfect for families, couples, and outdoor enthusiasts looking to relax and explore. Enjoy stunning lake views, a private dock, and endless activities, including swimming, boating, fishing, and kayaking. Unwind on the spacious deck, gather around the fire pit, or take a short drive to downtown Naples for dining, shopping, and local attractions.

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!

Lakefront family friendly gem

Maine living at its best. This lakefront, family-friendly home/camp has everything you need for a special stay. Even though you have no reason to leave, you are located 15 minutes from Portland, ME and a half hour from Freeport. You have 300 feet of lakefront for your swimming, kayaking and canoeing pleasure. Eight people can sleep comfortably and enjoy sunsets out the dining room window. Grill on the patio while the kids play on the two acres of lawn just steps away.

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.