Tiny house vacation rentals in Cumberland County

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Top-rated tiny house rentals in Cumberland County

Guests agree: these tiny house rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

A cozy living area features a comfortable gray sofa arranged near a light wooden coffee table. A large TV displays a streaming service, while natural light enters through expansive windows adorned with soft curtains. A small kitchenette is visible in the background.

Guesthouse in Brunswick

Modern Brunswick Tiny Home near Bowdoin & Downtown

WINTER 2026/27 NOTE: The main house on this property will be under construction. The tiny home will not be under construction and will be rentable, but you may hear construction noise during the day. A lofted bed space with additional optional pull out couch fitted with ergonomic foam mattresses. This space has air conditioning, heat, and amazing natural light. Brand new bathroom with rain shower head! A full kitchen with mini fridge, separate freezer space, oven, stove and coffee/tea supplies.

4.92 out of 5 average rating, 209 reviews

Top guest favorite

Tiny home in Bridgton

Cozy Library Tiny Home *Private Hot Tub* King Bed

Welcome to The Tiny Library - Maine's most unique tiny home! This antique library building has been newly renovated into a cozy getaway for bibliophiles and library lovers alike. Its book-lined shelves and dark academia decor, along with modern amenities and high quality bedding ensure a memorable stay, while the gas fireplace and hot tub provide the perfect ambiance for rest and relaxation. Whether you're a bookworm or just in need of a quiet escape, The Tiny Library is the perfect retreat.

4.98 out of 5 average rating, 204 reviews

Top guest favorite

The exterior of a post and beam cottage is shown, featuring a light wood facade and a brown shingled upper section. Two black Adirondack chairs are placed on a wooden deck, accompanied by potted plants. Large windows offer a view of the forested surroundings under a partly cloudy sky.

Cottage in Pownal

Dreamy Post&Beam Hideaway Near Portland & Freeport

Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.

4.99 out of 5 average rating, 487 reviews

Guest favorite

Home in Naples

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!

4.98 out of 5 average rating, 203 reviews

Top guest favorite

A tiny house with a grey exterior sits nestled among lush greenery and colorful flower beds. It features tall windows that allow natural light to flow in, and a bright red door that adds a pop of color. Surrounding steps made of stones lead up to the entrance.

Tiny home in Durham

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.

4.99 out of 5 average rating, 408 reviews

Top guest favorite

The image captures a serene riverside scene along the New Meadows River during sunset. Calm waters reflect the clear blue sky, while trees line the banks. Nearby, natural elements like rocky shores and patches of snow create a peaceful outdoor setting.

Cottage in West Bath

Coastal Waterfront Cottage in West Bath

***Please Message me to ask about possible discounts and length of stay minimums.*** 4 season home right on the waters edge on New Meadows River in West Bath sits this newly remodeled home. Fully furnished and includes a Minisplit Heat Pump/ AC, and Propane fireplace. Great location as it is on a dead end road that is just minutes to shopping, restaurants, etc. Incredible spot to watch the boats come and go as Sawyer park boat launch as well as the town boat launch are right in view.

4.94 out of 5 average rating, 140 reviews

Top guest favorite

A serene lakeside view reveals a wooden dock with a reclining chair near the water's edge. Vibrant autumn leaves frame the scene, contrasting with the clear blue sky and calm lake. Rocky terrain adds natural texture to the tranquil environment, inviting relaxation.

Cabin in Raymond

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.

4.93 out of 5 average rating, 187 reviews

Top guest favorite

Cottage in Oxford

Thompson Lake, No Cleaning Fee Pine Point Cottage,

A refurbish 1967 knotty pine."Cottage a short walk to lake and has lake rights. Located 400 feet from lake access." For swimming, FREE docking for your boat to fish, water ski or just cruise in Thompson lake. 14 miles one of Maines cleanest lakes. 6 Bicycles, 2- kayaks, 2-16 ft canoes, a 14 ft rowboat, and a paddle boat, fishing gear, firewood available for guest at no charge for fire pit. Propane and charcoal barbeques available at cottage. THERE IS NO WIFI.

4.96 out of 5 average rating, 188 reviews

Guest favorite

A cozy interior features natural wood paneling and beams. Two upholstered chairs are positioned near a large window, allowing light to fill the space. A small bookshelf holds several books, while kitchenware is organized on a nearby shelf. A white stove complements the rustic setting.

Cabin in Bridgton

Writers Cabin in the Woods with Sauna!

Nestled in the woods and on Adams Pond with new wood fired sauna! The cabin feels totally hidden away but is less than 10 minutes to Bridgton and Naples, hiking, beaches and restaurants. The woods are beautiful and peaceful and the pond is just down a mossy path. Great for couples or a weekend away. Large deck with grill and outdoor shower, firepit. There is a shared dock on the pond for swimming, fishing, or just enjoying the view as well 2 kayaks, and a paddle board.

4.94 out of 5 average rating, 208 reviews

Top guest favorite

The modern tiny home features a sleek exterior with horizontal siding and a dark roof. Two chairs are positioned on the covered entryway, accompanied by a small table adorned with a pot of flowers. Lush green grass surrounds the home, complemented by a newly paved pathway.

Tiny home in Scarborough

Cozy Fall Cottage • 9mi Portland

Escape the everyday in this charming, brand-new tiny cottage in Scarborough, Maine. The Greenhouse proves you don’t need a lot of square footage to live in style — just the right details. Wake up in a king bed, cook in a fully stocked kitchen, and unwind by the electric fireplace. When evening falls, string lights set the perfect mood for a quiet Maine night. Portland’s restaurants and breweries are 9 miles away. The beach is 6. Come home whenever you’re ready.

4.99 out of 5 average rating, 136 reviews

Top guest favorite

The exterior of the guest suite is shown, featuring a stone pathway leading to a glass door. Landscaping includes a decorative planter and natural stone elements, surrounded by greenery. A wooden fence provides privacy, creating a welcoming entryway to the space.

Guest suite in North Yarmouth

open concept Guest Suite in southern Maine

A short distance to many nature trails, Bradbury Mountain, state parks and the rocky coastline. This North Yarmouth guest suite is nestled between all the breweries and restaurants Portland has to offer as well as the famous outlet shopping in Freeport. We are located in a unique location where you are able to go from the rocky coast to the hiking trails all within 30 minutes. The guest suite is perfect for quiet lodging after a day of exploring or visiting.

4.97 out of 5 average rating, 155 reviews

Guest favorite

A charming cottage features a sloped metal roof and a welcoming entrance. Two chairs are positioned on the front porch, with a small table nearby. Lush green grass surrounds the cabin, complemented by flowerbeds and a large tree stump serving as a natural accent.

Cottage in Windham

Cozy camp near highland lake

If you're looking for a quiet, cozy get a-way steps from the lake this is the place. Lake is private with no public access so it’s not crowded. Close to everything but far enough away; highway (95), Portland, Sebago Lake Area. Boating, swimming, fishing, hiking at your finger tips. 4 kayaks provided. Big yard, great for games, BBQ or sitting by the fire pit. Listen to the loons from the front deck. Sorry no pets so please don’t ask if you bring one!

4.83 out of 5 average rating, 175 reviews