Family-friendly holiday rentals in Windham

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.

THE LILLIPAD.Off-grid A frame. Sebago lake region!

Take it easy in the woods at this cozy, off-grid A frame located in the Sebago Lakes Region. Kick back and relax around the fire while being "away from it all" yet still close by to great restaurants, beaches and more! This cabin is "off grid" and does not have running water or electricity. The space offers solar power that will power all lights, fans as well as charge devices. There is a battery operated pump that gives you potable water out of the sink. A porta potty is on property.

Edgewater Retreat - Lakefront w/Sauna & EV Charger

Welcome to Edgewater Retreat! This custom-built cottage features lakefront views and access to three beaches: secluded pocket beach in front of cottage, boaters beach with docks, and a full sun sandy bottom swim beach. Enjoy an unforgettable Maine vacation. Paddlecraft on the water, lounge in the hammocks, S'mores by the campfire, canoe to nearby island for offshore yoga, and gril with friends & family. In winter, enjoy ice fishing and kids enjoy snow sledding on adjacent hill.

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.

Sebago Sunrise Yurt - Trail Access!

Nestled between Portland's fine dining and Sebago's outdoor fun, the Sunrise Yurt is a great camping spot to explore what Southern Maine has to offer. Park & take a short walk to the back 2 acres of my property. The yurt overlooks a meadow & faces the sunrise. Located with access to the Sebago to the Sea Trail - 28 miles of walking & biking paths. .5 mile walking distance to Presumpscot River. *Please read 'Show More' notes section for important details.

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.

Sebago Lakehouse: Hot Tub and Private Beach Access

Lovely 3 bedroom/2 bathroom house in the woods with a Hot Tub and access to the private shared beach! Sebago Lake is a perfect family destination for swimming, boating, and fishing. It is ideally located for a day trip to Portland, Old Orchard Beach, Kennebunkport, or Freeport. Or stay home, enjoy the Lake or watch the stars from the Hot Tub. Close to grocery stores and restaurants. Lake and beach access is only a 5-minute walk.

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

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

Cottage Under a Crabapple Tree

Steps from extensive nature trails and wildflower meadows, this quaint studio cottage is nestled conveniently between the restaurants and breweries of Portland, the outlet shopping of Freeport, and miles and miles of rocky coastline. Perfect for a quiet Maine getaway, lodging near Cumberland fairgrounds and other local attractions, or a visit to family and friends in the area.