House holiday rentals in Carrabassett Valley

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!

Private Home Right On The River! Great Swimming!

An ideal haven for outdoor enthusiasts! Newly listed, this adorned home is 7 miles from Sugarloaf and provides a serene escape for activities like hiking, biking, skiing, hunting, or fishing. Nestled against the Carrabassett River, this residence offers 3 bedrooms, 2 bathrooms, a fully furnished kitchen, a snug living room with a wood-burning fireplace, a new sauna, flat-screen TV & laundry facilities. The dedicated owners are committed to ensuring your stay is both tranquil and unforgettable!

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.

Sugarloaf and Flagstaff Lake Area Vacation Rental

Nestled among the trees in a quiet, private neighborhood, yet close to area restaurants & amenities - this is the perfect house for the outdoor enthusiast! The open floor plan & entertainment system are ideal for relaxing after a full day outside. Outdoor dining area, grill, firepit, deck, & covered porch. Close proximity to hiking, biking, swimming, & more! 7 miles to Sugarloaf, 1.5 miles to Flagstaff Lake. An amazing spot to launch your adventures from & a guest favorite for many years!

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.

Mountain Escape | Views • Firepit • Near Sugarloaf

Perched high on Ira Mountain, this home features breathtaking panoramic views from nearly every room. Whether you’re sipping coffee at sunrise or watching the sun dip behind the peaks from the expansive deck, the scenery will be a highlight of your stay. With two beautifully appointed bedrooms, each offering comfortable beds and peaceful surroundings to ensure a restful night’s sleep. With three full bathrooms, there’s plenty of space for families or groups to spread out and enjoy privacy.

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.

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!

Black Bear Camp Flagstaff Lake

Enjoy a memorable visit when you stay in this cozy cabin that was part of the Original Black Bear Camps in Eustis. Home sits on 6 acres of private land and direct waterfront access to beautiful Flagstaff lake. Walk down to the water and enjoy. Less than 20 minutes to Sugarloaf Mountain and hiking on the Appalachian Trail and Bigelow mountain range. Just a short ride to Rangeley Lakes and Saddleback Ski area. There is access to snowmobiling trails across the street

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.

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!

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.