Holiday houses in Sugarloaf Mountain

4.98 out of 5 average rating, 171 reviews

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.

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

Looking for direct access to adventure? This is it! Space for 10 means 2 families easily fit. Trail access is just a few steps away, straight to the super quad. Want to start slower? Try the shuttle to the village! Need to unwind at the end of the day? Downstairs family room provides large couch, tv, games, puzzles, etc for the kids while the adults enjoy some quiet time in the upstairs kitchen/living room. Hot tub to ease muscles at the end of an adventurous day! *hot tub closed May-Oct*

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!

Apartment in Carrabassett Valley

The Summit View Hideaway

Kick back and relax in this quiet and stylish space. Brand new construction in a beautiful neighborhood. Away from the business on the mountain yet within minutes of access by a shuttle to all lifts. Bike in and out of the house for easy access to all bike trails on and off the mountain. Walking distance from the Rack and Minutes away from the golf course. Two bedroom apartment ready and equipped for short or longer stays with a full kitchen, washer/dryer. Bike rack and bike wash on site.

5.0 out of 5 average rating, 19 reviews

5.0 out of 5 average rating, 9 reviews

Modern Ski and Golf - West Mnt

New in 2021 4BR townhouse at Sugarloaf! Hot tub and pet friendly. Walk to the West Mnt Trail or hop the free shuttle to the base lodge. Features a master king suite, 2 queen bedrooms, full guest bath. Basement has a teen retreat including a queen bed and bunkbeds, a private bath, and living room. Two living areas with big smart TVs, mountain views, and a fully stocked kitchen. Steps from golf, hiking, and biking trails. Perfect for families or friends looking for year-round mountain fun!

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!

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 :)

4.89 out of 5 average rating, 140 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!

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.

4.92 out of 5 average rating, 313 reviews

Holiday 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.

4.89 out of 5 average rating, 130 reviews

A charming two-story ski house is nestled in a snowy wooded area, featuring large skylights on the upper floor. A spacious deck extends from the front, while two parked vehicles are partially covered in snow. Trees with autumn leaves frame the home.

4.96 out of 5 average rating, 108 reviews

Sugarloaf Home with amazing views

Sugarloaf Ski House, 10 minutes to baselodge, shuttle on call, awesome views, near crosscountry trails, restaurants, Outdoor Center. In summer months, 10 minutes to Sugarloaf Golf Course. Easy access to bike/ hiking trails, waterways, fishing. You can ski in and out from your vehicle from the ends of Lots E and F when the Bucksaw Quad is running. There's a ticket Kiosk at the base of the lift.

The open-concept living area features a spacious kitchen with a large island and seating. A cozy seating arrangement surrounds a coffee table in front of a stone fireplace. The room is brightened by natural light from large windows, enhancing the wood accents and warm tones of the decor.

4.98 out of 5 average rating, 60 reviews

Perfectly located 3-bedroom Sugarloaf condo

Recently renovated, comfortable condo with an ideal location close to Sugarloaf base area for easy access to alpine skiing out the front door or nordic skiing, back-country skiing, mountain biking and hiking out the back. 3-bedroom, 2-bath and open kitchen, living and dining area with a deck. Perfect for relaxing and recreating in the mountains.

Popular amenities for Sugarloaf Mountain holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Sugarloaf Mountain

4.91 out of 5 average rating, 11 reviews

Home in Kingfield

Mountain Escape | Views • Firepit • Near Sugarloaf

Chalet in Carrabassett Valley

The living room features vaulted wooden ceilings and large windows that provide natural light and views of the outdoors. A cozy seating arrangement with a sofa and armchair faces a stone fireplace, while a decorative lamp and coffee table add to the welcoming ambiance.

5BR chalet only 6 miles to Sugarloaf access road!

5.0 out of 5 average rating, 45 reviews

Apartment in Carrabassett Valley

Gondola Village at Sugarloaf

5.0 out of 5 average rating, 25 reviews

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!

5.0 out of 5 average rating, 17 reviews

A spacious cabin is nestled among trees, featuring a large deck with seating. The modern design includes multiple windows, allowing natural light to brighten the interior. The surrounding greenery enhances the tranquil setting, perfect for relaxation and outdoor activities.

5.0 out of 5 average rating, 49 reviews

Fun all season home on West Mountain.

Superhost

A spacious living area features a large sectional sofa with various cushions, complemented by a dark coffee table. A flat-screen television is positioned above a fireplace. Large sliding doors allow natural light and views of the outdoor space, framed by trees outside.

4.74 out of 5 average rating, 46 reviews

Condo near wiffletree chairlift!

4.89 out of 5 average rating, 35 reviews

Best location on the mountain! Park & Walk!

A living space features a modern fireplace framed by dark cabinetry. Two patterned armchairs are positioned around a wooden coffee table atop a plush area rug. A staircase leads to an upper level, while a well-equipped kitchen with wood cabinetry is visible in the background.