Family-friendly vacation rentals 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!

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.

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.

Two bedroom duplex across st from crystal lake

Relax, have fun, spend quality time with friends and family right here at our quiet little place. Two bedrooms, three beds, one pull out couch, we can accommodate up to six guests. We have walking trails, firepit, and a barbecue area. The house sits across the street from crystal lake, with a boat launch 3/4 mile down the road with a parking area. An easy 20-minute drive to Portland. Supermarket, gas station, and restaurant less than five minutes away and ten minutes from Gray exit to 95.

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.

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!

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.

Cozy camp near highland lake

If you're looking for a quiet, cozy get a-way steps from the lake this is the place. Lake is private with no public access so it’s not crowded. Close to everything but far enough away; highway (95), Portland, Sebago Lake Area. Boating, swimming, fishing, hiking at your finger tips. 4 kayaks provided. Big yard, great for games, BBQ or sitting by the fire pit. Listen to the loons from the front deck. Sorry no pets so please don’t ask if you bring one!

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.

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

Millers Private Studio on Highland Lake

If you're looking for a quiet, cozy getaway with private Highland Lake access this is the place for you. Private deck to enjoy your morning coffee, close to everything but in a country setting. 15 minutes from 95, Portland ME and Sebago Lake Region. Small boat launch available, Swimming & Fishing . Large back yard and a great window view of the lake. Wifi 1000(mbps) for a work from home atmosphere.

Naughty Dog Private Island Log Cabin

Naughty Dog Island is what happens when island time meets unapologetic canine freedom. This is a private island log cabin where you and your pup can truly be away away — no leashes once you arrive, no neighbors, no schedules worth keeping. Just you, your dog(s), and a 1,400-acre lake that becomes your shared backyard. If your dog has ever dreamed of running the show, this is their moment.