Cottage vacation rentals in Windham

Peaceful Cottage on Maine Flower Farm

Overlooking the gardens at Ferris Farm, our family-owned specialty cut flower farm, this charming cottage offers a peaceful retreat to relax and reconnect with nature. Take in garden views, sip coffee on the deck, wander through the flowers, kayak the river, and end your day with a cozy bonfire under the stars. Use the cottage as your home base to explore beaches, or head into Portland for breweries, coffee shops, and great dining. Perfect for a solo retreat, romantic escape, or work getaway.

Maine lakehouse 2.5 hrs from BOS, 40 min Portland

Beautiful lake living: 2.5 hours from Boston, 40 min. from Portland. This cozy 2-bedroom home on Lake Sabattus with 110 feet of private lake frontage, sleeps four. All the amenities of home incl. a SS kitchen with newer appliances, air conditioning. Minutes to Lewiston/Auburn - close to dining and stores. Spend your days swimming, canoeing, kayaking and fishing, use our grills or lobster pot to prepare your dinner and relax by the fire pit, toasting s'mores while watching the gorgeous sunsets.

Cozy & Quiet Modern Cottage

Modern studio cottage designed and maintained with sustainability and eco-friendliness in mind, located in a quiet and very safe Portland neighborhood only a 7-10 minute drive (and $10-13 Uber/Lyft ride) from downtown Portland, the Old Port, and most local attractions. The cottage is a walkable mile (+/-) from Allagash Brewing (and the 4 other breweries there), and is within walking distance (.5 mi) of the restaurants and bars at Morrill's Corner. This is an LBGTQIA- and BIPOC-friendly space.

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.

Relax by a Quiet Lake

Charming lakeside cottage only 29' from the waterline, w/65' of private waterfront. The cottage is a 3-season, classic L.C. Andrews, log-sided Maine summer lake home. Cozy atmosphere and a wonderful enclosed porch with amazing waterfront views. Enjoy fishing off the dock, hiking, canoeing, campfire, and exploring surrounding areas. Air conditioning units will ensure your comfort on warm summer nights and high-speed internet will keep your devices connected. Furnishings are family mix.

#1 Cozy cottage minutes from the beach!

3 night Min. 6/1 to Labor Day. This charming one bedroom cottage is beautifully decorated with a blend of vintage pieces and modern decor, creating a cozy and stylish atmosphere. It features a fully stocked kitchen, complete with pots and pans, perfect for cooking when you choose to stay in. The cottage also includes a private patio with a gas grill and outdoor seating for your enjoyment. Just a short 7-minute walk to the beach and pier. And yes, pets are welcome at no extra charge.

Taproot Cottage at Stone Mountain

Taproot Cottage is cozy, quiet, comfortable and nestled in the beautiful White Mountain foothills of Brownfield, ME. Just one mile from the Stone Mountain Arts Center, 30 minutes to North Conway, NH, and easy access to hiking trails, mountain vistas, and the Lakes Region of western Maine. It offers a well-equipped kitchen/dining/ living room combination, full bath, a relaxing sunroom with full-sized futon for additional sleeping, and a loft bedroom with a queen bed.

Modern cozy cottage in historic coastal Maine

Contemporary, newly-renovated cottage between Portland and Freeport. Spotless interior w/ full kitchen, Netflix/AppleTV+, premium Tuft+Needle bed, and washer/dryer. EV charging available. Walk down Main Street to shops, restaurants, and the scenic Royal River. Easy drives to downhill skiing and iconic beaches, Portland's renowned restaurants, LL Bean flagship, and top-rated Maine Brewing. Half way between Boston and Sugarloaf. Your ideal base for Maine adventures.

Sunset Haven - Little Sebago Lake

Sunset Haven is a beautiful 3BR, 1.5 bath year round lakeside cottage on Little Sebago Lake in Gray, Maine. It boasts a private beach and water frontage in the heart of Maine's Sebago Lakes Region. Located only about half an hour max from Portland, Maine and the Atlantic coastline, approximately an hour or less from Shawnee Peak and the Sunday River Ski areas, 40 minutes from Oxford Casino, this area is truly a great destination for four season recreation.