Holiday houses in Portland

Moss House: A Modern Waterfront Cabin in the Woods

Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

Glass Wall Waterfront Hot Tub Fireplace Tiny Home

Wake up to rushing waterfalls right outside your glass wall in this romantic waterfront tiny home in Norway, Maine! Private hot tub with river views, see-through gas fireplace, cozy raised queen bed overlooking the water, outdoor shower, hammocks, and direct access to hiking trails. Total privacy—no neighbors in sight. Modern kitchen, heated floors, fast WiFi, and thoughtful touches for couples or solo escapes. Romantic getaway near Sunday River skiing, golf & Maine adventures. Nature's oasis

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.

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

Luxury Retreat In Back Cove | 10 Min to Downtown

Bike to downtown just 2 miles away. Ideal for a couple or family looking for a restorative getaway in a quiet, locals neighborhood. The architect owner designed and built this light-filled spacious eco-suite to meet the needs of the most discerning guest with luxurious accommodations. Organic and down-topped king mattress, linen bedding, spacious marble rain shower, deep soaking tub, fenced in backyard with deck, hammock, and pool - everything you need for a memorable Maine vacation!

Portland Back Cove Hideaway-1 BR- With Patio

Our quiet residential Back Cove neighborhood is your perfect retreat from a busy day exploring Portland. Take a short drive to the center of the city, or enjoy the waterfront walking and biking trail which loops around the cove. Dine at Tipo or Woodford F&B, two neighborhood favorites. Come home to this newly renovated space and relax on the patio! Our space can accommodate four guests. Great for a family, or close friends! We look forward to hosting you!

Downtown Penthouse Suite - Stunning Harbor Views

CO2024-01992 Private 1850's Old Port Penthouse w/Breathtaking Views and Complimentary Parking Nearby. Gorgeous contemporary suite full of light located right across from the working waterfront. Lobster and seafood off the boat is 100 meters from your front door. Watch ferries and smell the salt air from your private deck. Welcome to Portland! Please note: animals (including assistance animals) not allowed due to owner's health.

The Garden Cabin Tiny Home

Curious about tiny homes? Love dogs, gardens, pine trees, campfires, and birds? Hate cleaning fees? Our private 128 sqft cozy cabin is for you! On the spectrum between camping and a hotel room, it's a chill place to call home while visiting Portland. Enjoy our garden while sipping a beverage from your own deck or around the campfire. Heat and A/C in the cabin. Please, no smokers, kids under 7, or guest pets. STHR-000718-2018

Modern Condo Portland's Historic Old Port District

Enjoy a stylish experience at this centrally-located loft. A converted factory building has been transformed into this chic and modern condo. Cobblestone streets, endless incredible dining and nightlife, boutiques, shops and historic architecture. A quintessential New England seacoast town and working waterfront.

INCREDIBLE! Waterfront views. 94 walk score.

Wow! Incredible 3 bedroom, 2 bath apartment with working waterfront views. Spacious apartment nestled in Downtown, between the Old Port, Arts District and West End, just steps away from all the highlights of the peninsula. You are just steps away from everything the City has to offer. STHR-000508-2018

Tiny house in the Birch Grove with private HOT TUB

Quaint tiny house that is surrounded by white birch trees in a quiet country setting with a private hot tub. Centrally located to Freeport shopping outlets (25 min), Old Port, Portland (40 min), Pineland Farms (New Gloucester (10 min)), Bradbury Mountain State Park (15 min) nearby Golf Courses

Chic Portland Penthouse, 2BR

Enjoy a stylish experience at this centrally-located place. We are in the middle of all the excitement in the Old Port. Ride down the elevator and just out our front door you are steps to all the best that Portland has to offer. Shops, dining and night life all conveniently at your door step.