Family-friendly vacation rentals in Carrabassett Valley

4.88 out of 5 average rating, 435 reviews

A cozy living area features a modern electric fireplace encased in rustic wood, complemented by a circular coffee table. Soft seating offers comfort, while a wall-mounted television is positioned above. An adjacent entry leads to a spacious eat-in kitchen, creating an inviting environment.

Apartment in Kingfield

On The River

On the River, airbnb is located in the heart of downtown Kingfield right off the snowmobile trail. Sleeps 6 people. Has a spacious eat-in kitchen with a vie looking out to the Carrabassett River. Steps away from galleries, gift shops, restaurants, bank, Stanley Museum. 20-minute drive up to Sugarloaf mountain ski resort and the breathtaking views of 4000ft peaks of the western mountains of Maine. In summer, fly fishing and swimming right out the back . In winter, there are many snow sports.

Indoor spacesKitchenAmenities

A cozy living area features a comfortable sofa and an accent chair beside a stylish table. A propane fireplace is framed by wooden shelves displaying decorative items. A flat-screen TV is positioned on a wooden console, with board games and books available for guest use.

4.97 out of 5 average rating, 125 reviews

Cozy Ski-In/Ski-Out Escape at Sugarloaf with AC

Cozy ski-in/ski-out condo in Sugarloaf’s desirable Sugartree complex. Wake up, click in, and ski out. Enjoy effortless slope access, mountain adventures, and relaxing après ski memories. Perfect for families, couples, and outdoor enthusiasts year-round, with hiking, mountain biking, golf, and foliage outside your door. Mountain views from your private balcony, plus indoor access to the pool, hot tubs & sauna at the Sugarloaf Fitness Center (add’l fees apply). Full kitchen, and AC for summer!

Indoor spacesKitchenWalkability

Train in Carrabassett Valley

A restored red caboose is surrounded by freshly fallen snow, softly illuminated by warm indoor lighting. Snow-covered trees frame the scene, creating a cozy yet secluded atmosphere. The structure showcases its original features, contrasting with the winter landscape.

Train Caboose on Mountain

Sugarloaf Village 1 - on mt ,w free shuttle. featured in "Maine Homes by Downeast" mag "Love Train". This beautifully restored caboose w/3 separate sleeping areas - a master bedroom w full bed - single comfortable bunk and a convertible couch. Fully equipped w many ammenities- Flat Screen tv w chromebox- tiled shower -great bedding/linens- full stove & microwave.-fridge- pots pans & cooking supplies -keurig & trad coffe pot-great deck & 1 1/4 yard w pines . U-Tube video JohannaFowler-x5w

FamilyIndoor spacesHiking

4.95 out of 5 average rating, 194 reviews

5.0 out of 5 average rating, 128 reviews

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.

FamilyKitchenHeating

4.99 out of 5 average rating, 142 reviews

A tranquil outdoor space features a wooden pergola with seating and a grill, situated beside a hot tub. The fenced backyard is surrounded by tall trees, and the charming house is accentuated by a beautiful sunset sky.

Cabin in Kingfield

Cozy Cabin with Modern Amenities. Pet Friendly!

Kick back and relax in this beautifully renovated home with amenities you didn't know you were missing. Despite its small stature, every square inch is utilized, boasting 4 beds and 1.5 bathrooms, including a huge shower with multiple shower heads and hurricane force water pressure. Located on a quiet street just minutes from the Kingfield village, steps from the snowmobile trail system, and 20 minutes from Sugarloaf. Designed with dogs in mind, complete with a fenced in backyard.

Indoor spacesFamilyCheck-in

4.97 out of 5 average rating, 116 reviews

First Tracks at Sugarloaf

Welcome to First Tracks! Located right on mountain bike trails and less than a three minute walk to Sugarloaf Village. With epic hiking, waterfall swims, disc golf, zip lining and mountain biking right out the back door we've got your vacation covered. Plenty of room to spread out in the condo with a game room downstairs and a hot tub to soothe your tired muscles after a day of play. Sugarloaf in the summer is magical. Let us know if you need any recommendations!

Indoor spacesKitchenParking

Chalet in Carrabassett Valley

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.

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 :)

FamilyKitchenHeating

4.89 out of 5 average rating, 141 reviews

Chalet in Carrabassett Valley

The charming wooden house features a gabled roof and large windows framed in white. A welcoming front porch is visible, and flower beds with assorted greenery enhance the entrance. An American flag is displayed, complementing the natural surroundings.

Hillside Hideaway - Great Location & Hot Tub

Welcome to our cozy Sugarloaf/Carrabassett Valley home! Sitting in the back of Redington is our private home with a hot tub, firepit & grill! There is ample parking for you & your friends. Hiking/snowshoeing trail is 100 yards into the woods out of the back of the house. Check us out on the gram @hillsidehideaway_2039. About 10 minutes from the base of Sugarloaf mountain. Family friendly, wi-fi, decked out kitchen. Feel at home within minutes!

KitchenIndoor spacesCleanliness

4.93 out of 5 average rating, 134 reviews

Home in Carrabassett Valley

A serene riverbank is framed by lush green trees and foliage. Clear water reflects the surrounding nature, with smooth stones scattered along the shore. Gentle ripples indicate flowing water, creating a tranquil atmosphere for outdoor activities.

4 Bed 1 Bath on River: Skiing & Mountain bike!

Quiet get away for the family on the river. Hear the sound of the flowing water right outside the windows. 4 Bedroom, 1 Bath, mudroom, radiant floor heat and propane gas stove, full kitchen, with deck and grill. Only a mile from Sugarloaf mountain and the Outdoor center and 24 miles from Flagstaff Lake. Activities include: cross country skiing, skate skiing, downhill skiing, skating and mountain biking, hiking, fishing and golfing.

KitchenIndoor spacesHeating

4.92 out of 5 average rating, 133 reviews

4.99 out of 5 average rating, 115 reviews

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

Flagstaff Oasis Endless Sunsets

Flagstaff Oasis is your winter retreat just 10 minutes from Sugarloaf! Ski all day, then come back and warm up by the fireplace. 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!

KitchenIndoor spacesBeach

Cabin in Carrabassett Valley

An outdoor seating area features a circular stone fire pit surrounded by a blue rug. A wicker couch with blue cushions provides comfortable seating, accompanied by a wicker coffee table. French doors lead into the cabin, complementing the rustic wooden exterior.

Private Cabin next to Narrow Gauge Trails & River

Historic Ski camp built in 1957! Located a mile from Sugarloaf access road. View of Sugarloaf! Private trail to the Narrow Gauge Parking lot & Trail system. Biking and Hiking right out the door! Only a 4 minute drive to Super Quad and on the Shuttle route. Located within a mile from Anti~Gravity Center, Outdoor Center, Hugs restaurant, Carrabassett Public Library, Mountain Side Grocery Store & Gas station.

KitchenFamilyValue

4.91 out of 5 average rating, 314 reviews

Vacation home in Carrabassett Valley

The Loaf View - 3 Bed Apt - 10 min from Sugarloaf

Relax, ski, snowshoe, mountain bike, hike or just flake out in our spacious three-bedroom lower-level apartment in Reddington East -- just 10-minutes from the Loaf. 1500 square feet, fully equipped kitchen, comfortable living area great for watching the game, blazing fast internet, and a spectacular view of the mountain. There's plenty of room for your skis, coats, and other items in the secure entryway.

Indoor spacesKitchenNearby

4.89 out of 5 average rating, 130 reviews

Popular amenities for Carrabassett Valley family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Apartment in Carrabassett Valley

The open interior features wooden beams and a cozy living area with a light brown sofa and a wooden coffee table. A dining table with black chairs accommodates up to six people. The well-equipped kitchen includes a stove and refrigerator, with sunlight illuminating the space.

Sugarloaf post & beam 2 bdrm apt, great location

Indoor spacesKitchenAccess

4.79 out of 5 average rating, 102 reviews

Superhost

A serene view of Flagstaff Lake is visible, with a wooden dock extending into the water. Surrounding greenery frames the scene, creating a peaceful environment. The backyard features a hot tub, patio furniture, and an outdoor space suitable for relaxation and leisure activities.

Cabin in Eustis

Lakefront Cabin, Dock, Hot Tub, Ski Sugarloaf 12mi

FamilyKitchenCheckout

4.88 out of 5 average rating, 110 reviews

4.95 out of 5 average rating, 103 reviews

The exterior of a log cabin is showcased, featuring a large deck with wooden railings. A bank of large windows allows natural light inside, highlighting the cabin's open design. Stacks of firewood can be seen underneath the deck, ready for use.

Home in Phillips

Hurry Back.

KitchenFamilyComfort

4.98 out of 5 average rating, 145 reviews

A peaceful outdoor deck is showcased with two red Adirondack chairs facing a panoramic view of rolling hills and a clear blue sky adorned with clouds. Lush greenery surrounds the area, enhancing the natural setting.

Chalet in Sandy River

On-Mountain @ Saddleback-Hot Tub | Mountain Views

KitchenIndoor spacesCleanliness

Cabin in Carrabassett Valley

The spacious living area features wooden walls and large windows that allow natural light to fill the space. Two comfortable chairs and a brown sofa are arranged around a rustic coffee table. A dining table is positioned nearby, with views of the surrounding woods.

Bubblecuffer Cabin: On shuttle Route w/Hot Tub!

FamilyIndoor spacesAccuracy

5.0 out of 5 average rating, 17 reviews

A living area features a stone fireplace with a wooden mantel, overlooking expansive windows that provide mountain views. A large couch is positioned centrally, complemented by a coffee table. The space includes a flat-screen TV and a bar area with high stools, all set on wooden flooring.

4.92 out of 5 average rating, 49 reviews

Spacious 4 BR Condo in Carrabassett Valley

Indoor spacesKitchenGetting around

Vacation home in Carrabassett Valley

A cozy living area features a stone fireplace as a focal point, surrounded by a patterned area rug. Seating includes a patterned armchair and a rocking chair, with a window dressed in red curtains. A compact television is placed on a dark cabinet.

Spacious, ski on-ski off at Sugarloaf!

Indoor spacesKitchenComfort

5.0 out of 5 average rating, 31 reviews

Vacation home in Carrabassett Valley

An open living area is displayed, featuring a stone fireplace as a focal point. Comfortable seating options include two patterned armchairs and a neutral sofa. A dining table for 10 is visible, complemented by a well-equipped kitchen area. Natural light flows through several large windows.

Ski-in, Ski-out Timbers 4-Bedroom condo

Indoor spacesKitchenCheck-in

4.92 out of 5 average rating, 50 reviews

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 161 reviews

A single-story house is displayed, featuring a light-colored exterior and a metal roof. The building is surrounded by green grass and trees, with a gravel driveway leading to a garage on the right. A peaceful, natural setting is evident.

Home in Kingfield

Quiet 2 bedroom home, snowmobile from property.

FamilyKitchenHiking

Cabin in Carrabassett Valley

A rustic ski camp is surrounded by snow-covered trees, with soft illumination coming from a window. The building, featuring natural wood accents and a sloped roof, is partially obscured by snow drifts, creating a serene winter landscape.

Sugarloaf Mountain, Slim Melvin House

FamilyKitchenQuiet

4.9 out of 5 average rating, 115 reviews

4.93 out of 5 average rating, 133 reviews

The spacious living area features warm wood paneling, providing a cozy ambiance. Comfortable seating arrangements are positioned around a central area rug. A dining table is visible in the foreground, and doorways lead to bedrooms. Soft lighting illuminates the space from recessed ceiling fixtures.

Apartment in Eustis

Eustis Ridge Lodge

Indoor spacesKitchenCheckout

4.92 out of 5 average rating, 180 reviews

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

Indoor spacesKitchenSleep quality

5.0 out of 5 average rating, 126 reviews

The cabin is gently illuminated under a starry night sky, showcasing its welcoming facade. Surrounding trees create a natural frame, while soft snow blankets the ground, enhancing the serene winter atmosphere.

Cabin in Kingfield

Peaceful - Private - Paradise -- The Sugar Shack

FamilyKitchenRiver

4.95 out of 5 average rating, 145 reviews

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)

Indoor spacesKitchenLocation

4.89 out of 5 average rating, 158 reviews

An open concept first floor showcases natural wood elements, with a spiral staircase leading to the loft. A wood stove is positioned near large south-facing windows, allowing natural light to enhance the space. A cozy seating area is complemented by a stack of firewood and greenery.

Cabin in Coplin

Cozy Cabin close to Sugarloaf Mountain

KitchenIndoor spacesTV

4.98 out of 5 average rating, 161 reviews

Home in Kingfield

Mahoney Manor

Indoor spacesFamilyComfort

Family-friendly home rentals with a pool

4.87 out of 5 average rating, 191 reviews

A vibrant sunset spreads across the sky, displaying shades of orange, pink, and purple. The calm waters of Rangeley Lake reflect these colors, while silhouettes of trees line the shoreline, creating a serene landscape. Mountains are visible in the distance under a dynamic cloud formation.

Chalet in Rangeley

A+ View Relax Hike & Fish * w/SpaTub/Sauna

FamilyKitchenTV

Apartment in Carrabassett Valley

An open living area showcases a comfortable seating arrangement with gray sofas, complemented by a light coffee table. A dining table with wooden chairs is positioned near the well-equipped kitchen, featuring wooden cabinetry and modern appliances. Windows allow natural light to brighten the space.

Sugarloaf Ski-In/Ski-Out Condo w/ Pool

FamilyKitchenPool

4.87 out of 5 average rating, 45 reviews

A large, colorful sign reading 'SUGARLOAF' is positioned prominently among a cluster of rocks. Lush greenery and trees provide a natural backdrop, complementing the partly cloudy sky.

4.97 out of 5 average rating, 69 reviews

On Mountain Sugarloaf Condo

KitchenIndoor spacesPets

The exterior of a multi-story condo building is displayed, featuring a deep red wooden facade and multiple balconies. A wooden walkway leads to the entrance, surrounded by greenery, with cloudy skies overhead.

4.95 out of 5 average rating, 94 reviews

Ski-in-ski-out-sugarloaf-condo

Indoor spacesKitchenLayout

Apartment in Carrabassett Valley

Ski In Ski Out, Winter Mountain Escape Pool Access

KitchenLocationHospitality

5.0 out of 5 average rating, 8 reviews

A cozy living area features a real wood fireplace with a brick surround and a television mounted above it. A plush red sofa with decorative pillows faces the fireplace, complemented by a coffee table designed for games. A door leads to a bedroom area in the background.

4.86 out of 5 average rating, 51 reviews

Sugarloaf w/ Pool, Hot Tub, Shuttle & Trail Access

KitchenIndoor spacesOutdoor spaces

Home in Carrabassett Valley

The exterior of the condominium is shown, featuring a modern design with gray siding. Balconies are visible on the upper floor, and large windows allow for ample natural light. Lush greenery surrounds the building, creating a serene environment.

SUGARLOAF, TRAILSIDE, 4-BDRM, & AC

FamilyKitchenValue

4.85 out of 5 average rating, 88 reviews