Family-friendly vacation 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.

1 of 1 pages1 / 1

Top guest favorite

A bright sitting area features large windows offering scenic views of Porter Lake and surrounding mountains. Wooden walls create a cozy atmosphere. A comfortable couch sits adjacent to a flat-screen TV. Nearby, a bookshelf displays a variety of books, enhancing the inviting space.

Cabin in Strong

Lakefront Home w/ Dock | Porter Lake | Sugarloaf!

Lakefront paradise on Porter Lake with a private dock, swim float, spacious yard, hammock, deck, patio, grill, fast WiFi, smart TVs, and all the comforts of home. Enjoy direct access to Maine’s ATV and snowmobile trail network right from the property, plus excellent fishing, boating, kayaking, swimming, & ice fishing. Just 20 minutes from Farmington and 35 minutes from Sugarloaf Resort and the Bigelow Mountains. Experience Maine lake living at its finest in every season with stunning lake views

KitchenIndoor spacesDecor

4.92 out of 5 average rating, 176 reviews

Top guest favorite

A spacious farmhouse stands amidst a grassy area, illuminated by warm light from numerous windows. A covered porch extends along the front, featuring wooden chairs. The surrounding landscape includes mature trees providing a natural backdrop.

Home in Starks

Farm house, River, Island, animals & private Chef.

MARCH-APRIL DAILY. Medicine Hill is a 136 acre farm on the Sandy River complete with a swimming hole and an entire island to explore. We grow vegetables, herbs & flowers. Our animals include sheep, chickens & rabbits. You will have full access to all areas of the farm! Spend time fishing or relaxing on the river. Or literally just sitting on the porch unwinding and taking it all in. 4 private bedrooms have stunning views surrounded by trees or fields. And if the Chef is available..EAT!!!

KitchenFamilyValue

4.94 out of 5 average rating, 171 reviews

Top guest favorite

A cozy chalet is situated in a snowy landscape, framed by tall, bare trees. The wooden exterior combines rustic charm with modern design. A covered entrance welcomes guests, leading to a snow-covered pathway surrounded by a serene, wintry environment.

Chalet in Kingfield

Pristine, Peaceful Kingfield Chalet

Just a short 15-20 minute drive from Sugarloaf and 3 minutes from historic downtown Kingfield, this chalet provides a peaceful, private respite after a busy day on the mountain. Our 2BR, 1BA eco-friendly chalet is tucked back from the road, with distant neighbors and fast WiFi. You can be surrounded by nature but only minutes from lovely restaurants, local shops, grocery store, gas station and tons of trails, rivers & lakes for snowshoeing, XC, snowmobiling, hiking, huts, MTB, kayaking & more.

FamilyIndoor spacesRiver

4.98 out of 5 average rating, 171 reviews

Top guest favorite

A comfortable seating area is illuminated by natural light from a large window, offering a view of the water. A cozy throw is draped over the couch, and a decorative coffee table holds various magazines. A dog rests peacefully on the couch.

Cabin in Rangeley

Your Pet Friendly, Maine Escape, on Haley Pond!

Park the car and walk to all things Main Street, Rangeley has to offer. Serenity out back with direct access to Haley Pond, and every convenience out front…a walk across the street to Rangeley Lake and a 15 minute drive - door to chair lift at Saddleback! Explore hiking, biking, fishing, hunting, snowmobiling - you name it - everything is at your fingertips. We are true Mainers and look forward to welcoming you to our cute little cabin - your home away from home - the way life should be!

FamilyIndoor spacesValue

4.97 out of 5 average rating, 162 reviews

Top guest favorite

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

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.

FamilyKitchenWifi

5.0 out of 5 average rating, 127 reviews

Top guest favorite

A serene scene features a person fishing by the river, surrounded by lush greenery and mountain views in the distance. The interior showcases wooden beams and a spacious kitchen with stainless steel appliances, complemented by bar stools along a large island.

Home in Eustis

New Cabin. Mountain, River & Dam Views, Kayaks.

Newer home! See the beautiful leaves changing colors. Use the 2 Kayaks. Sugarloaf 20 mins away for Skiing biking & hiking or hop on the ATV & Snowmobile Trail right from the dooryard. Jacuzzi jetted tub, fireplace, D/W, pans, etc. High Speed wifi/internet - login to your streaming devices on the Smart TV (3TV’s). Window views of the historic Dam, River & Mountains. The Dead River just steps away to float, fish, & take in the cascading sounds of the Dam. Trails End Restaurant steps away!

KitchenIndoor spacesQuiet

5.0 out of 5 average rating, 100 reviews

Top guest favorite

Apartment in Eustis

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!

FamilyIndoor spacesNearby

4.99 out of 5 average rating, 120 reviews

Top guest favorite

The cabin's exterior showcases a rustic wooden facade surrounded by tall spruce trees. A spacious gravel area provides ample parking. The covered porch, adorned with seating, invites relaxation. A small storage shed is positioned to the right of the cabin.

Cabin in Rangeley

Evergreen Lodge-Rangeley Cabin, 3 bedroom & Loft

The perfect Home Base. Minutes to Saddleback, 1.5 mi to downtown with beach and boat ramp. Secluded in a very quiet, family freindly association neighborhood Direct ITS snowmobile access, NO ATV access. The home is very private, yet close to all Rangeley amenities. The Home boasts 3 bedrooms, two full bathrooms, fully equipped kitchen, memory foam mattresses throughout, Smart TV's in all bedrooms, hi speed wifi & plenty of parking for trucks & trailers. Any questions just ask.

FamilyKitchenWalkability

4.99 out of 5 average rating, 153 reviews

Guest favorite

Home in Le Granit

The Rifugio Rental Cottage Hot tub/mountain view

The rifugio is the perfect place to take refuge. A peaceful oasis in the heart of nature, surrounded by mountains as far as the eye can see. The Rifugio gives you the freedom to connect authentically with nature and to enjoy quality time, whether alone or with others. The minute you walk through the door, you are welcomed into a warm and cozy atmosphere. Large windows offer magnificent views of the surrounding mountains, and in the distance, we can see the tip of Lake Mégantic

Indoor spacesKitchenQuiet

4.97 out of 5 average rating, 154 reviews

Guest favorite

A cozy living area features natural wood walls and a wooden floor. Multiple seating options, including chairs and a plush lounge cushion, are arranged around a coffee table. A propane stove stands next to the entrance, and natural light fills the space through large windows.

Chalet in Carrabassett Valley

Welcome to our Shackteau! Close to loaf + trail!

Unique ski chalet five minutes from Sugarloaf access road, with snowshoe / XC ski trail from the property that connects to valley trail system. Cozy, all-wood interior with funky bunk bed tower, homey propane stove, and den with bar and large TV. Equally well-suited for families, friends, and responsible mountain enthusiasts! We love our shackteau and know you will, too! We received negative feedback on our last cleaner so we have a new AWESOME cleaner :)

KitchenIndoor spacesRiver

4.89 out of 5 average rating, 140 reviews

Top guest favorite

A charming exterior of The River House is depicted with its wooden siding and multiple windows. Colorful Adirondack chairs are arranged in the foreground, complemented by the spacious lawn. Tall trees surround the property, and a deck provides access to the inviting outdoor space.

Home in West Forks

River House in West Forks trail access ITS 86 & 87

The River House is located in downtown West Forks near Berry's Store. Close to whitewater rafting, hiking trails, & fishing. Big backyard great for lawn games, fire pit for nightly campfires. Plenty of room for ATV trailer parking and a huge backyard right on the Dead River. Intersection of ITS 86 and 87 across the street, easy trail access. Six restaurants within five miles, also accessible by trails. All new bedding, mattresses, appliances, and furniture.

FamilyIndoor spacesPets

4.98 out of 5 average rating, 141 reviews

Top guest favorite

A log cabin with a welcoming design features four prominent gabled windows on the upper level. The earthy tones of the wood blend harmoniously with the surrounding greenery. A wooden walkway leads from the lakeside, enhancing accessibility to the cabin's entrance.

Cabin in Weld

Camp Bai Yuka/Little Camp (Log Cabin on Webb Lake)

Enjoy your stay on the banks of Webb Lake in our 2019 hand-crafted log cabin. This cabin is 35 ft from the high water mark and has views of the lake from all three bedrooms. This rental has access to a private beach ( 200 ft) and is in a secluded cove on the lake. For travelers unfamiliar with Weld, Maine, Weld is nested in the heart of the western mountains of Maine. Hiking Tumbledown and Mt Blue are only the beginning of the recreational opportunities.

KitchenIndoor spacesView

4.95 out of 5 average rating, 141 reviews