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Family-friendly holiday rentals in Flagstaff Lake

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Flagstaff Lake

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

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Top guest favourite
The log cabin, set against a clear blue sky, features a peaked roof and large windows that reflect the natural surroundings. A front porch with a railing extends from the cabin, surrounded by patches of snow and green trees, enhancing its secluded ambiance.
Cabin in Andover
5 out of 5 average rating, 189 reviews

Mountain Time Cabin,Spectacular Views! Secluded!

Looking for a mountain cabin getaway? You have found it here at Mountain Time Cabin! This cabin is new and absolutely beautiful! Located in the Western Mountains of Maine - a true paradise for the outdoor enthusiast. Bring your Snowshoes,Skies,Snowmobiles, or hike right from the front door with a 130 acres of trails to explore. Enjoy the spectacular views of the mountains and the cascading brook all from sitting in the recliners with the warmth of the pellet stove Has AC and pool table.SECLUDED!

Top guest favourite
The exterior of the cabin is illuminated at dusk, highlighting the wooden structure and large windows. A hot tub is visible on the deck, surrounded by trees, inviting a serene and relaxing atmosphere. Warm light glows from inside, suggesting a cozy interior.
Cabin in Kingfield
4.95 out of 5 average rating, 148 reviews

Apres Ski Haus

This cabin is anything but ordinary! Nestled on an open bluff in the woods of Kingfield, Maine this architectural wonder is a perfect getaway for a couple or group. It's a warm and cozy space to come back and unwind after a long day of hitting the slopes or any four season activity. The open concept living room and newly remodeled kitchen have modern amenities like an espresso machine, Smart TV, and comfortable furnishings that will make you feel at home. Only 20 minutes to Sugarloaf Mountain!

Top guest favourite
A cozy cabin is nestled among snow-covered trees, showcasing a wooden exterior in warm tones. The entrance features a welcoming pathway lined with snow, while the nearby deck offers a glimpse into the winter landscape, creating a serene atmosphere in the snowy environment.
Cabin in Hanover
4.99 out of 5 average rating, 507 reviews

Cabin retreat just steps from adventure

Nestled on 80 acres in the woods alongside a stream, this cabin is the perfect retreat. Whether you are looking for a romantic getaway, a family vacation, or a gathering of your closest friends-this cabin is ideal. It is located on a private road and close to Howard Pond, Androscoggin River, and Sunday River skiing. No matter the season, opportunities await, whether you decide to stay close or venture out. There are plenty of trails nearby to explore, canoe rentals, skiing and so much more.

Top guest favourite
An open living space reveals a kitchen with a wooden island and white cabinetry, connected to a dining area featuring a wooden table and chairs. Steps lead to a cozy sitting area with a sectional sofa, surrounded by large windows allowing natural light.
Home in Eustis
5 out of 5 average rating, 115 reviews

Sweet home nestled in quiet spot; Walk to dining.

Situated at the end of a dead end street, Rockstar Quarry House is a place where you can relax and unwind with Deer regularly grazing right in the backyard. Walk to Fotter's grocery, Backstrap Grill, both just a stone's throw away. Here, in the center of Stratton, in the western mountains of Maine, an 8 mile drive to Sugarloaf and 27 miles to Saddleback. Whether you're here to ski, cycle, swim, snowmobile, hike or anything else you can think of, this region will provide the opportunity.

Top guest favourite
A rustic lower-level apartment is nestled among pine trees, surrounded by a blanket of snow. The red exterior is complemented by a spacious deck adorned with lights. The inviting entrance is flanked by outdoor decorations, highlighting the property’s charm in its natural setting.
Flat in Eustis
4.99 out of 5 average rating, 112 reviews

The Dead River Ranch-16 miles from Sugarloaf

A rustic, cozy lower level apartment that offers open space for a couples retreat. Steps away from Pumpkin Pond to the North Branch of Dead River. Enjoy boating on near-by Flagstaff Lake, fishing, hunting, ATV/snowmobile riding for miles on end! Short walk to Trails End Steak House and Tavern. Skiing or golfing at Sugarloaf Mountain is less then 25 minutes away! Come enjoy provided coffee in the Great Northern outdoors, and when available fresh chicken eggs when our hens are laying!

Guest favourite
Home in Moscow
4.87 out of 5 average rating, 217 reviews

Beautiful home on Wyman Lake

This large one bedroom two bath "camp" is located on Wyman Lake directly off Rt. 201, about 8 minutes north of Bingham. This is a wonderful location to unwind and decompress. The perfect place to ice fish with the kids. Watch the flags from the window or while your roasting marshmallows in the fire pit. Bring your snowshoes (or rent ours) and take your dog on an adventure around the lake. We offer trailer parking for your snowmobiles in Bingham, and you can ride them to the camp.

Top guest favourite
An outdoor soaking tub with a white finish is positioned near the water's edge, surrounded by a gravel area. String lights hang overhead, providing soft illumination. A serene view of the lake is visible, framed by lush trees, as evening twilight casts a calming atmosphere.
Cottage in Sidney
4.92 out of 5 average rating, 155 reviews

Waterfront Cottage

The Waterfront Cottage sits directly on the shores of Snow Pond, 15 minutes from Colby College and downtown Waterville and 1/2 mile from the Snow Pond Center for the Arts. Enjoy the BEST sunset views from the private dock and listen to the waves and loons at night. The private front deck is the perfect spot for a sunset cocktail after a day of swimming and kayaking from the sandy beach. You also have a private outdoor hot soaking tub and water view barrel sauna. Paradise!

Top guest favourite
A spacious living area features a stone fireplace integrated with natural wood accents. Light-colored furnishings include a plush sectional sofa adorned with a soft throw blanket. Large windows offer views of the outdoors, enhancing the bright and airy atmosphere of the room.
Home in Beaver Cove
4.93 out of 5 average rating, 134 reviews

Moosehead Lake, Snowmobile Trails, Hot Tub

Unwind, recharge and reconnect at our beautiful house on Moosehead Lake. A short path takes you down to the lake and a pebble stone beach to swim, use our 4 kayaks, soak in our 4 season outdoor hot tub, or just relax with a good book. Access both the snowmobile and ATV trails from the driveway! Plenty of parking for trailers for all of your powersport toys. The Beaver Cove Marina is a short drive away and provides convenient access to launch your boat for the day.

Top guest favourite
A charming cabin with a screened-in porch is illustrated, featuring a door leading to the outdoors. A rainbow flag is displayed, adding a touch of vibrancy. A small potted plant sits next to the entrance, while a grill is positioned on the porch, enhancing outdoor cooking options.
Cabin in Rangeley
4.95 out of 5 average rating, 219 reviews

The Terraces #5 Private Lakefront Cabin

Cabin #5 is available spring to fall. It is cozy getaway located on Rangeley Lake. Guests have access to the lake via 100 meter walk down to the dock. You will be a less than a 5 minute drive to a bustling main street with great local shops and eateries. The cabin is accessible by 2 sets of stairs or a path from the parking lot. The cabin is quaint and we provide the necessities. That being said, there is not a microwave or electric coffee maker.

Top guest favourite
A tranquil view of a lake at sunset, showcasing vibrant hues of orange and pink reflecting off the water. Silhouetted trees line the horizon, providing a serene backdrop to the colorful sky.
Cabin in Eustis
4.99 out of 5 average rating, 106 reviews

Flagstaff Oasis

Flagstaff Oasis is your winter retreat just 10 minutes from Sugarloaf! Ski all day, then warm up in the large heated mudroom built for skis and gear. Enjoy direct snowmobile trail access with plenty of parking for sleds and trailers. After the adventure, gather at the firepit or relax in the cozy cabin with all-new appliances and a fully stocked kitchen. Peaceful, private, and set on Flagstaff Lake—perfect for skiing, sledding, and winter fun!

Top guest favourite
A relaxing hot tub is positioned on a wooden deck surrounded by trees, overlooking the serene landscape. A person sits at the edge, holding a glass, with soft sunlight filtering through the foliage, creating a peaceful atmosphere.
Treehouse in Belgrade
5 out of 5 average rating, 129 reviews

SkyView Treehouse | Lakefront • Private Hot Tub

Welcome to your dream treehouse escape — tucked among the pines with stunning lake views, a private hot tub, and direct access to Belgrade Stream. Designed for couples, honeymooners, and small families, SkyView Treehouse offers a luxurious retreat in nature. Enjoy starry nights in the hot tub, cozy evenings by the fireplace, and peaceful mornings on your private deck. Rustic charm meets upscale comfort in this unforgettable lakeside getaway.

Guest favourite
A wooden cabin with a green metal roof is situated in a wooded area. The front porch features ample seating and a welcoming sign that reads 'Moose Mountain Lodge.' Surrounding trees and a gravel area enhance the natural setting.
Cabin in Greenville
4.91 out of 5 average rating, 157 reviews

Moose Mountain Lodge - Vacation with Nature

Living within nature. Moose Mountain Lodge is tucked away in the woods on a sunny lot with great views where wildlife sightings far exceed the occasional car that may pass by on the road. It is not uncommon to wake up to 5-10 deer in the back yard or a moose walking down the road. All this and the center of Greenville, the heart of the Moosehead Lake Region is just 5.5 miles down the road. See below for a complete description.

Popular amenities for Flagstaff Lake family-friendly rentals