Family-friendly vacation rentals in Flagstaff Lake

Your Pet Friendly, Maine Escape, on Haley Pond!

Park the car and walk to all things Main Street, Rangeley has to offer. Serenity out back with direct access to Haley Pond, and every convenience out front…a walk across the street to Rangeley Lake and a 15 minute drive - door to chair lift at Saddleback! Explore hiking, biking, fishing, hunting, snowmobiling - you name it - everything is at your fingertips. We are true Mainers and look forward to welcoming you to our cute little cabin - your home away from home - the way life should be!

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.

Train Caboose on Mountain

Sugarloaf Village 1 - on mt ,w free shuttle. featured in "Maine Homes by Downeast" mag "Love Train". This beautifully restored caboose w/3 separate sleeping areas - a master bedroom w full bed - single comfortable bunk and a convertible couch. Fully equipped w many ammenities- Flat Screen tv w chromebox- tiled shower -great bedding/linens- full stove & microwave.-fridge- pots pans & cooking supplies -keurig & trad coffe pot-great deck & 1 1/4 yard w pines . U-Tube video JohannaFowler-x5w

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 Dead River Ranch-16 miles from Sugarloaf

A rustic, cozy lower level apartment that offers open space for a couples retreat. Steps away from Pumpkin Pond to the North Branch of Dead River. Enjoy boating on near-by Flagstaff Lake, fishing, hunting, ATV/snowmobile riding for miles on end! Short walk to Trails End Steak House and Tavern. Skiing or golfing at Sugarloaf Mountain is less then 25 minutes away! Come enjoy provided coffee in the Great Northern outdoors, and when available fresh chicken eggs when our hens are laying!

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.

MONT CHALET in the 1st Dark Sky Reserve 🌠

Mont Chalet is located in Estrie in the small village of La Patrie. About fifteen minutes from Mont-Mégantic National Park. This cottage WITHOUT electricity, offers you the desired comfort by being totally independent. Wood heating, refrigerator, stove and hot water are functional with propane gas and lights thanks to 12 volt batteries. Skiing, snowshoeing and walking are possible on this 270-acre land. One visit and you'll be charmed. Come and admire the starry sky 🌟

Treehouse With Hot Tub Close to Sunday River!

This authentic, luxury treehouse was designed by B'Fer Roth, DIY Network TV host of The Treehouse Guys and built by the Treehouse Guys. Nestled in the woods on a quiet, private rd with no neighbors in sight, the treehouse is just 15 minutes to Sunday River Ski Resort, 5 minutes to Mt. Abram and 10 minutes to downtown Bethel. The treehouse is abutted by 626 acres of Bucks Ledge Community Forest (7 miles of hiking/snowshoeing trails accessible from the treehouse).

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 :)

Private lakefront cabin Flagstaff Oasis.

Flagstaff Oasis is your winter retreat just 10 minutes from Sugarloaf! Ski all day, then warm up in the large heated mudroom built for skis and gear. 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!

The Blue Gondola in Western Maine Apt.#1

The Blue Gondola is Ten minutes north of Sugarloaf Ski area. Minuets from Flagstaff lake, Local Markets, Bars and Restaurants. All with in walking distance. The area offers Mountain Views as well as Fishing, Boating, Hiking, Biking, Tours and lift rides depending on the seasons. As well as Cross Country Skiing, Snowmobiling and Ice Skating. Come explore for yourself the Mountains of Western Maine.

Trailside Cabin

Come & play in the beautiful mountains of western Maine! Cozy, rustic cabin for two. Enjoy miles of multi use trails right off the front steps! If you decide to venture away from the cabin, Rangeley's Saddleback Mt & Sugarloaf USA are both 35 miles away & the college town of Farmington is just 15 minutes south. Our cell service is terrific, but there's no tv or wifi...come to the woods & unplug!