Vacation rentals with outdoor seating in Carrabassett Valley

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.

The Maine Frame // A Private Getaway

Enjoy your own personal A-Frame cabin tucked away in the mountains of the Carrabassett Valley. The Maine Frame is a private getaway with easy access to Sugarloaf Ski Resort, numerous hiking trails, unique local eateries, and multiple lakes and rivers for kayaking in Maine’s Western Mountains & Lakes Region. The cabin features high-speed internet for streaming movies on rainy nights, quick access to Kingfield for food and supplies, and a large wooden deck for lounging and entertaining at home.

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!

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.

The cottage at Marble Farm.

This beautiful private cottage is the perfect place to unwind after a long day of adventure! New, bright and comfortable, this secluded cottage is conveniently located just 40 minutes from Sugarloaf, 50 minutes from Saddleback and 10 minutes to downtown Farmington. Feel free to walk, fat bike or x-country ski on nearly 4 miles of groomed private trails located just outside your front door! Contains a full kitchen for meal prep, as well as high speed internet, and climate control.

Sugarloaf and Flagstaff Lake Area Vacation Rental

Nestled among the trees in a quiet, private neighborhood - great for walking, 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. Close to hiking & biking trails, 7 mi to Sugarloaf, 1.5 mi to Flagstaff Lake, 20 min drive to Rangeley. Outdoor dining area, grill, firepit, deck, & covered porch. The perfect spot to launch your outdoor adventures from!

Brivera in the Mountains-20 min to Sugarloaf!

Brivera in the Mountains is a classic 4‑bedroom, 3‑bath log cabin tucked into the woods—perfect for unplugging, adventuring, or simply relaxing. Four seasons of activities at your doorstep: skiing, snowmobiling, hunting, fishing, biking, hiking, boating, dining out, stargazing, or sleeping in—You can make your getaway as peaceful or adventurous as you like. Just 20 minutes to Sugarloaf, 45 minutes to Saddleback, and only minutes from ITS trail access.

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!

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.

Cozy Camp/Hot Tub/Ski Mountains/Lakes/Trail Access

Cozy camp located in the heart of the Western Maine Mountains. Enjoy relaxing in the hot tub after a long day of skiing, snowmobiling or whatever sport your into. Snowmobile and ATV right from the cabin. Short drive to Sugarloaf Mountain/Bigelow Mountains Hiking Trails/Local Restaurants/Kayaks available on request 2 days before arrival. Outdoor firepit & lawn furniture. Outdoor patio table. Corn hole & other outside games.

Flagstaff Oasis Endless Sunsets, Sauna May 2026!

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!

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.