Holiday houses in Flagstaff Lake

Perfect Getaway Cabin; Close to Sugarloaf

Relax with the whole family at this peaceful “barn” cabin close to everything you want in western Maine. Great proximity to both Sugarloaf and Rangeley and easy access to beautiful Flagstaff lake. ATV trails 1/2 mile away and you can snowmobile right from the cabin during the winter!Our beautiful cabin has everything you need to feel right at home and relax. 2 bedrooms, 1 bathroom, plus a bunk room means you have plenty of sleeping space for your whole crew to kick back and enjoy your getaway.

Family · Location · Quiet

Lakefront Home w/ Dock | Porter Lake | Sugarloaf!

Lakefront paradise on Porter Lake with a private dock, swim float, spacious yard, hammock, deck, patio, grill, fast WiFi, smart TVs, and all the comforts of home. Enjoy direct access to Maine’s ATV and snowmobile trail network right from the property, plus excellent fishing, boating, kayaking, swimming, & ice fishing. Just 20 minutes from Farmington and 35 minutes from Sugarloaf Resort and the Bigelow Mountains. Experience Maine lake living at its finest in every season with stunning lake views

Family · Location · Heating

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.

Location · Value · Air conditioning

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.

Family · Value · Barbecue

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!

Family · Location · Decor

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

Location · Family · Sleep quality

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 :)

Value · Location · Biking

River House in West Forks trail access ITS 86 & 87

The River House is located in downtown West Forks near Berry's Store. Close to whitewater rafting, hiking trails, & fishing. Big backyard great for lawn games, fire pit for nightly campfires. Plenty of room for ATV trailer parking and a huge backyard right on the Dead River. Intersection of ITS 86 and 87 across the street, easy trail access. Six restaurants within five miles, also accessible by trails. All new bedding, mattresses, appliances, and furniture.

Value · Location · Barbecue

Camp Bai Yuka/Little Camp (Log Cabin on Webb Lake)

Enjoy your stay on the banks of Webb Lake in our 2019 hand-crafted log cabin. This cabin is 35 ft from the high water mark and has views of the lake from all three bedrooms. This rental has access to a private beach ( 200 ft) and is in a secluded cove on the lake. For travelers unfamiliar with Weld, Maine, Weld is nested in the heart of the western mountains of Maine. Hiking Tumbledown and Mt Blue are only the beginning of the recreational opportunities.

Family · Value · Walkability

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.

Location · Family · Access

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 tables, large deck, & propane grill. 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!

Family · Location · Comfort

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!

Value · Family · Quiet