Holiday rentals in Cumberland County

A-frame w/ towering 18ft glass wall & deck - 15

The Escape is a gorgeous A-frame cabin that features an 18' wall of glass overlooking beautiful woods. It is set among the tranquil northern pines of the recently renovated campground on the edge of the famous dunes of the Desert of Maine. The cabin has everything you need to enjoy a luxurious, relaxing outdoor experience. It is just a short walk away from the Unwind Nordic Spa which includes a sauna, hot tub, plunge pool, cold plunge, and more. Disconnect from the world at this beautiful A-fram

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.

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.

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.

Nestled Treehouse | 65 Acres, Pond + Kayak

Escape to your own treehouse, nestled around a beech tree in 65 private acres of Maine forest. Peek through the trees to our 25-acre natural pond. • ✅ Dock & kayaks & trails • ✅ Fire pit under the stars and by the water • ✅ Wildlife & beautiful views • ✅ Only 8 miles to grocery store and restaurants • ✅ 2.5 miles to Sebago Lake state park - 45 minutes to Portland • ✅Enclosed outdoor bathroom with skylight A romantic, unplugged getaway in the Sebago Lakes region. Book your escape today!

Dockside Dreams

Welcome to Dockside Dreams, your year-round retreat on the shores of Sebago Lake. This thoughtfully updated Maine cottage is a perfect blend of rustic charm and modern convenience. Inside, you'll find warm wood finishes, exposed beams, and an open-concept layout that creates a cozy yet spacious feel. Large windows and sliding doors bring in beautiful natural light and open to a lakeside deck, offering sweeping views of Sebago Lake with your own dock for boating, swimming, and waterfront fun!

The Modern Lakehouse

This modern lakehouse is situated on Hogan Pond in Oxford Maine. Here you can stay with all the comforts of a beautiful lakehouse built in 2020 while being feet from the water. This is a great place to vacation whether you prefer the private sandy beach, the A/C inside complete with Smart TV cable and Wifi, or the hottub! Sip a drink at the bar while watching the game or use the grill on the deck but be sure to use the built in sound system to play your music throughout the house and deck.

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!

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.

The Copper Fox Treehouse

Named the 10th most spectacular tree house in the world by the BBC Featured in the book: Modern Tree Houses by Taschen Airbnb's Most wishlisted property in Maine in 2025! Come experience the whimsy and craftsmanship of this red fox head shaped treehouse for yourself. The magic of this wild adventure awaits you in the treetops... Come to relax, explore and make lasting memories your family and friends will talk about for years. Follow our journey on IG at @thecopperfoxtreehouse

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

Mermaid's Chair | Private Beach | Hot Tub

*Hot tub not available after October 27- April This is a rare one. A classic 1939 Maine camp sitting directly on Casco Bay with a private dock, sweeping water views, and a saltwater hot tub, all on a quiet private road. Properties like this don't come around often, and once you're here, you'll understand why. The dock puts you right on the water, with one slip available for guests. Wolf's Neck State Park and Wolf's Neck Farm are a short walk away, and Downtown Freeport.