Holiday rentals in Flagstaff Lake

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.

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.

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.

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!

Flagstaff Lakeside Cabin Retreat

This newly renovated house is located in a private community on Flagstaff Lake surrounded by beautiful mature red pine trees with your own private spot on the lake complete with a dock & swim ladder! Amenities include a fire pit, picnic table, large deck, & propane grill. Kayaks & paddle-boards are available for an extra fee. You are close to endless hiking & biking trails, 10 mi to Sugarloaf & 25 mi to Rangeley. This is the perfect spot to relax & launch your outdoor adventures from!

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!

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.

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

Stream-side mountain retreat

This attractively renovated camp in the High Peaks region of western Maine is the perfect place to get away and unplug. Surrounded by conservation land, the camp is airy and bright, with views opening onto woods and stream, and is well screened. Solar panels provide water and electricity. There's limited satellite internet service for emailing and texting, and sometimes phone through wifi, depending on your service provider.

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!

Summits Refuge, panoramic view and sauna

Cabane hors-réseau en altitude avec une vue panoramique exceptionnelle sur les Appalaches. Situé à l'orée du bois sur une terre de 100 acres, vous vivrez des levers et couchers de soleil inoubliables. Un poêle à bois, un lit queen confo, un sauna, une vue, la paix ! Si vous recherchez une pause nature en mode de vie minimaliste pour vous reconnecter au moment présent et vous inspirer, ne cherchez pas plus loin !