House holiday rentals in Sugarloaf Mountain

Condo near wiffletree chairlift!

3bdr, 2 bath, 7bed. Sleep 10, perfect for 2 families! Steps from Wiffletree chairlift & MTN bike trails, near fitness center, restaurants & golf course. Out from the 70s, condo has nothing fancy, but has a LOT of heart & feels like 2nd home. 2 families (9 kids!) usually share it. Expect a fully functional place with many games. Bring your food, belongings & outdoor gear. Spend the day searching for powder & relax at night in front of the fireplace, where spirits of Amos Winter & Bob Marley meet!

Family · Value · Accuracy

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.

Location · Family · Access

Carriage House

Renovated circa 1920 carriage house in a quaint New England college town. Eight-minute walk to busy downtown with restaurants, bars, shops, and grocery store. Elegant contemporary style. Open concept downstairs with sofa, daybed (napping in the sun!), and chef-designed kitchen. Second level with two queen beds and small balcony. Adjoins miles of walking trails and forest, full of wildlife. Less than 5-minute drive to a 1.5 mile running trail along the Sandy River, with refreshing swimming.

Location · Family · Quiet

Ski-In Ski-Out Condo Perfect for Families!

Prime Location: Access the Condo Cross Cut trail right behind the condo, or take a leisurely 6-10 minute stroll to the Sawduster Chairlift and the popular Shipyard Brew Pub. Outdoor Space: Unwind on the porch after a thrilling day on the mountain. Fun for Everyone: Challenge your friends and family to a game of ping pong in the game area—perfect for friendly competition! Accommodations: Our 3 bedrooms and 3 bathrooms, plus a fun lower-level twin bunk bed, ideal for kids or extra guests.

Family · Location · Laundry

Mahoney Manor

My father executed his vision and built Mahoney Manor from the ground up. What started as a "camp" eventually became his full-time home before his untimely death in 2018. Nestled in the woods at the base of Ira Mountain just minutes from Sugarloaf and along the Carrabassett River, Emmett created a sanctuary. He spent the last years of his life "developing" two empty lots into a Zen-like nature trail system with hand made bridges and benches perfect for 4-season walking or snowshoeing.

Value · Family · Access

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!

Location · Family · Condition

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!

Location · Family · Skiing

Fun all season home on West Mountain.

Bring the whole family to this great place with lots of room for fun. Ski, golf, hike, bike, or just relax. Basement has bar and all the games you need to entertain. Pellet stove will keep you warm after a full day of skiing. Located on West Mountain so can grab the lift or take the shuttle that picks you up right at the end of the driveway. Plenty of space for family and friends. 4 bedrooms that sleep 8 but extra couches and mattresses.

Location · Family · Laundry

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.

Value · Family · Air conditioning

The Riverfront Retreat - 27 minutes to Sugarloaf!

This vibrant farmhouse is surrounded by 800 ft. of Lemon Stream. Walk to the historic wire bridge! It is about 27 minutes to Sugarloaf and 8 minutes to Kingfield; located directly off Rt. 27 in route to Carrabassett Valley. You can hit the slopes then come home to a cozy, gas fireplace. There's a firepit by the stream to enjoy the stars in warmth. The home is full of color and organic decor. FAST STARLINK WIFI!

Value · Family · Getting around

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.

Location · Value · Hospitality

Spacious in town location

Welcome to a lovely, spacious home away from home. This gem has a full kitchen, a large dining room with seating for 8, a comfortable living room, a workspace, a half bath and a bedroom on the first floor. Head up the beautiful staircase to the remaining three bedrooms and two full bathrooms. Only a 20 minute drive to Sugarloaf. Up to two well behaved dogs are welcome!

Location · Value · Nearby