Family-friendly vacation rentals in Highland Lake

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Highland Lake

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

A serene lakefront view showcases a cozy cottage surrounded by lush trees displaying vibrant autumn colors. The still water reflects the landscape, enhancing the tranquil scene of nature. Gentle ripples and scattered rocks can be seen along the shoreline.

Cottage in Whitefield

4.96 out of 5 average rating, 248 reviews

Lux Waterfront Cottage with Private Island

Luxurious Cottage on pristine private pond. Hot Tub! Outdoor wood fireplace, kayaks & gas fire table. Graceful bridges lead to your Private Island with screened gazebo and hammock. Have coffee or cocktails on the deck with mountain and lake view or hike the trails on our 68 acres to the Gold Mine Trail. With a full kitchen, fine china, new shower, Jacuzzi bathtub, electric fireplaces, and two workspaces, this dog-friendly luxury cottage has it all! Make memories in this charming retreat!

Guest favorite

A spacious kitchen features white cabinetry with modern hardware and a large island with a wooden countertop. Black appliances, including a refrigerator and stove, complement the granite countertops. A window above the sink allows natural light to enter, enhancing the functionality of the space.

Home in Bridgton

4.91 out of 5 average rating, 316 reviews

Lake Region Comfort, Close to Everything!

Come enjoy the Highland Lake area known for its clear water, boating and fishing! Just a few miles away from Shawnee Peak which offers both day/night skiing. Also a few miles away is downtown Bridgton where there is the Magic Lantern movie theater and the drive-in theatre. Downtown also offers shopping and many options for superb dining. This single-family residence will provide you with 3 bedrooms, a newly renovated kitchen, sliders to deck, bathroom, living room with large panel tv and WiFi.

Guest favorite

A chalet-style home is nestled among tall trees, featuring a wooden deck with a set of stairs leading down to the ground. Large windows provide glimpses into the living spaces, welcoming natural light into the interior.

Home in Bridgton

4.88 out of 5 average rating, 162 reviews

Moose Pond Mountain Escape

A two minute walk to Moose Pond and one mile from Pleasant Mtn skiing in picturesque Bridgton, Maine. This cozy retreat is perfect for those who want a relaxing getaway in a fun-filled area in the heart of the lakes region. Guests enjoy a short walk to Association's beach/dock access and kayaks, and a short drive to tennis courts and pool. Hike, bike and explore Western Maine's mountains, lakes and villages. Bridgton shops are 5 miles away while N. Conway's outlets are 20 miles to the east.

Guest favorite

A small, wooden dock extends into Jewett Pond, featuring two teal Adirondack chairs positioned towards the water. Lush green hills rise in the background, reflecting the serene setting. The calm water invites relaxation and offers unobstructed views of the surrounding nature.

Cabin in Waterford

4.89 out of 5 average rating, 152 reviews

Jewett Pond Retreat

Relax in the Western Maine Foothills at our cabin on Jewett Pond. The main cabin has 672 sq ft of finished living space with bedroom (queen bed), bathroom, basic kitchen, great room (queen sleeper sofa), and screened porch. There is an additional rustic bunkhouse with two twin beds. This space is ideal for a couple or adventurous family who enjoys swimming, canoeing, hiking, fishing, or sitting on the screened porch with a good book and pine forest backdrop. Canoe included with booking.

Top guest favorite

A spacious bedroom is furnished with a king-size bed featuring a plaid bedding set. Two windows allow natural light to enter, complemented by a bedside lamp. Wooden accents, including a wardrobe and a small table, enhance the room's warm ambiance.

Guest suite in Freeport

4.97 out of 5 average rating, 238 reviews

Waterfront Private Apartment only 5 min to LLBean!

Guest apartment with private entrances, king bed, pull out sofa, kitchenette, walk-in shower, and porch facing the water providing the perfect relaxing coastal Maine experience! Custom built home on 8 acres tucked away in the woods with waterfront access to Harraseeket Cove & South Freeport Harbor, great for kayaking! Located 5 minutes from LL Bean and Freeport's many shops, restaurants, bars, etc. Wolfes Neck State Park and its stunning coastal trails and forests are less than a mile away.

Superhost

Two wooden chairs are positioned on a deck, facing a serene pond surrounded by vibrant autumn foliage. A small table rests between the chairs, and the expansive sky is filled with clouds, adding to the tranquil atmosphere of the natural setting.

Home in Harrison

4.9 out of 5 average rating, 308 reviews

Riverfront Luxury in the woods, Million $ Views.

Secluded A-frame nestled along Crooked River, breathtaking views and world-class fly fishing beckon. Swim in the river or explore scenic hiking trails right from your doorstep. Inside, savor modern comforts including central AC. Just minutes from pristine lakes, primo golf courses, and thrilling ski slopes, this charming private oasis offers an ideal mix of tranquil relaxation and outdoor adventure. Book your unforgettable getaway today and immerse yourself in this one-of-a-kind retreat!

Guest favorite

A serene outdoor space features a fire pit surrounded by natural stone. Lush greenery extends to distant mountain views under a partly cloudy sky, creating a peaceful setting for relaxation and outdoor gatherings.

Cabin in Tamworth

4.9 out of 5 average rating, 514 reviews

Luxurious Mountainside Cabin! Fantastic Views!

Cozy Cabin with Sweeping Mountain Views! A great escape with total privacy. Relax by the Giant Fire Pit overlooking the Mountains! Head up to North Conway to the White Mountains or go South to the Lakes Region. Then escape the traffic and retreat to the quiet of your Mountainside Cabin. Wood Fired Sauna on the premises! We provide everything you will need for your stay, and I mean everything, just bring a sense of adventure! Pets ok! *Pet Fee Applies! *Additional Fee for Sauna

Guest favorite

A compact kitchen area is shown, featuring a full-size refrigerator, stove, and sink with countertop space. Cabinets are installed above and below the counter. A cozy futon couch is positioned in the foreground, complementing the warm wooden paneling on the walls.

Home in Albany

4.82 out of 5 average rating, 451 reviews

Cozy Guest Suite in White Mountain National Forest

Guest Suite, mother-in-law apartment with private entrance. One bedroom with living room, dining area, kitchen, stove, full refrigerator. WiFi and a futon couch that turns into a bed in the living room. The converted basement apartment is a comfortable, and cozy place to stay while visiting the Mount Washington Valley. Perfect for adventuring, climbers, hikers, bikers and skier/snowboarders. Have a hot pot of organic local coffee and get outside in the beautiful Mount Washington Valley!

Guest favorite

The image showcases a bright interior with vaulted ceilings, featuring large angular windows that allow natural light to fill the space. A rustic brick fireplace with a black stove is centered against a wall. A wooden ceiling fan hangs above, enhancing the cabin-like atmosphere.

Home in Waterford

4.85 out of 5 average rating, 239 reviews

Maine Lakes Region house (private hot tub)

Cozy new construction, Chalet style, year-round house, on 9 wooded acres. Lots of Privacy, Short drive to Ski slopes, snowmobile trails, hiking, or beautiful lake to swim, or kayak. Gage beach a 10-minute drive. Close to great hiking, Also Shawni peak and Sunday River. Great restaurants, Mt Washington, NH shopping outlets. Full Desk / office, 200 mb of streaming. Wi-Fi, Netflix via ROKU, Canines only, NO CATS, NO EXCEPTIONS. Portable generator in the event of a power failure provided.

Top guest favorite

An aerial view showcases a spacious home surrounded by lush greenery and a golf course. Nearby, a parking area is visible, along with manicured fairways and trees in the distance, providing a sense of tranquility and openness.

Home in Bridgton

4.95 out of 5 average rating, 101 reviews

Beautiful Views, Bridgton Maine

Vacation getaway for all seasons. Enjoy mountain and golf course views from this 3,800 square foot home. Pleasant Mountain Ski Area beckons from 10 minutes away. Sunday River Ski Area is 40 minutes away. Or bring your clubs and test your skills on the challenging 18 holes at Bridgton Highlands Golf located steps away. At the end of the day, sip on an adult beverage in the spacious timber frame great room and marvel at the field-stone fireplace that stretches from floor to the ceiling.

Superhost

A serene lakeside view reveals a wooden dock with a reclining chair near the water's edge. Vibrant autumn leaves frame the scene, contrasting with the clear blue sky and calm lake. Rocky terrain adds natural texture to the tranquil environment, inviting relaxation.

Cabin in Raymond

4.93 out of 5 average rating, 155 reviews

Rustic, cozy cabin on Sebago Lake. A hidden gem.

Step out of the screened in patio to lakeside relaxation. Dive into crystal waters, snorkel or float with a cool beverage. Kayak or canoe out to Turtle Cove and enjoy the wildlife in this natural waterway teeming with birds to include our resident Blue Heron, ducks, geese, and loons who make this place their home. We have the fortune of bald eagle pairs in several tall pines. Turtles sunning on doting rocks and lily pads in bloom greet us each day. It is a natural water landscape.

Guest favorite

The cottage features a rustic wooden exterior with a large wrap-around porch. Two Adirondack chairs are positioned on the porch, offering a welcoming spot to enjoy the surrounding nature. A large window allows light to enter the space, enhancing the warm atmosphere.

Cottage in Bridgton

4.91 out of 5 average rating, 185 reviews

True Maine Artist Cottage with Outdoor Shower

Featured on Huckberry!! Beautifully decorated seasonal artist cottage with brand new soaking tub and outdoor shower. Solo stove fire pit and Adirondack chairs. Huge wrap-around porch with outdoor seating and glorious sunset views across blueberry fields. Also amazing stargazing!! Close to Naples, Bridgton, Sebago Lake. Tons of lakes nearby, hiking, swimming, boating, restaurants, music and local beer! Great place to stay to explore the area or also just relax and hang out.