Holiday houses in Windham

Tranquil waterfront cottage

A private clean tranquil cottage, dock, parking, deck, grill, hammock, kitchen & all amenities, bathroom, 2 bedrooms, sleeps 5, futon, WIFI, cable, bidet, washer & dryer, granite outdoor table, kayaks, paddle boards, floats, fire pit and fireplace. Minutes from great restaurants, bars, hiking trails, and shopping. The most amazing sunsets. 30 minutes from Portland. Winter rentals as well. 40 min. from Shawnee Peek, 1 mile from Seacoast tubing. This place is privately yours. Smoke free please!

LUX Designer Private Waterfront Hot Tub - Secluded

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.

Lakefront | Dock + Fire Pit Near Sebago & Portland

Experience the charm of Forest Lake just 28 mins from Sebago & Portland! Swim, kayak, paddleboard, or unwind on your private beach. Enjoy BBQs & bonfires in the spacious yard under the stars. Sleeps 7. Fully stocked home with 72" OLED TV, PS5, surround sound, and fast Wi-Fi. New heat pumps ensure comfort year-round. Whether you're after lakeside peace or easy access to southern Maine's best spots, your perfect escape awaits. Explore local trails, beaches, breweries, & classic Maine lake towns.

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

Coveside on Little Sebago

Welcome to our lakefront home on Little Sebago Lake in Gray, Maine. Have morning coffee on the patio while listening to wildlife. Kids enjoy the beach with shallow water entry, while boaters appreciate the deeper water at the dock! Westerly view of glorious sunsets. Gardens, wildlife, great star viewing! 7 day minimum in the summer. 4 mi. from Gray Exit #63 of the Maine Turnpike I-95. 2 hrs from Boston. 30 min to Portland or Oxford Casino, 60 min to Shawnee Peak, 74 min to Sunday River.

1 Bedroom with Beach Access

This beautifully converted 1860s carriage house loft blends historic charm with modern comfort. Tall vaulted ceilings showcase the exposed beams of the original timber framing, while a sliding barn door adds rustic character to the space. Nestled in a tranquil neighborhood, the apartment offers beach access to our neighborhood's pond—perfect for swimming or kayaking on sunny days. Conveniently located near North Windham businesses, 9 minutes from I-95 in Gray and 25 minutes from Portland.

Covered Bridge Cottage - Maine woods and river

Covered Bridge Cottage is on the Presumpscot River. Historic Babb's bridge adjoins the property. This peaceful, secluded woods cottage sleeps 5. Eat-in kitchen, dishwasher, full bath with washer and dryer. Wifi, Sony TV, a/c , heat, weber grill, porch. Use of dock, 2 kayaks, floats, campfire, picnic table, hammock. A wonderful spot to relax and explore the river. Swim in shimmering water. Portland 12 mi., beaches, or Sebago. owner has dog and chickens and lives next door .

Maine Vacation Home on the Water

Create memories with family and friends at this well loved waterfront home with plenty of fun to be had whether you’re spending the day floating down the lazy ‘river’, swimming at the small association beach, kayaking on the pond or enjoying meals and games inside. Downtown Windham is minutes away (there is some traffic noise at the property) and has nice shopping and sweet restaurants while Portland is just 16 miles with everything Maine’s largest city has to offer.

The Roost - lovely one bedroom efficiency unit

Staying at the Roost means you will be 15 minutes to the ocean, the airport and to the Old Port; 10 minutes to nearby lakes and rivers; 5 minutes to everything downtown Westbrook has to offer, including many restaurants, parks, live music venues, shopping and a movie theater: what you are looking for is nearby! Kick back and relax in this calm, stylish space with a queen-sized bed, kitchenette, dining/work area, excellent wifi, a full bathroom and a big yard.

The Retreat at Crystal Lake Farm

This getaway features two spacious bedrooms plus an upstairs bedroom loft, sleeping up to 6 with ease. The large bathroom is accessed by both the master bedroom and living room and features on-site laundry. For guests who love to cook the kitchen is fully equipped and the deck is a perfect place to relax in the summer and enjoy the view. In colder seasons guests are encouraged to cozy up by the wood-burning stove or use the outdoor BARREL SAUNA.

Cottage on Black Brook Preserve

This charming cottage is thoughtfully furnished, it's your home away from home! Clean and cozy, one bedroom with queen size bed and full kitchen. Sit in front of the gas fireplace or on your own private deck overlooking the 105 acres of Black Brook Preserve. Take a hike, snowshoe or cross-country ski right outside your door. We now have new sofa, bed, refrigerator, stove, as well as shower and bathroom flooring.

Cozy cottage near Sebago Lake

Cozy & adorable house (cottage) close to Sebago Lake. Backyard with fire pit. Great for those who like boating, swimming, fishing, skiing, snowmobiling. You are close to everything; Sebago Lake State Parks, several areas to launch a boat or visit one of the area beaches (house does not have lake access but plenty of access nearby). Less than 2 miles from grocery stores & restaurants/bars. Sorry no pets!l