House vacation rentals in Flagstaff Lake

4.98 out of 5 average rating, 128 reviews

A telescope is positioned beside large windows, offering a clear view of a sunset over a snowy landscape. The scene is framed by evergreen trees, with a peaceful lake reflecting the warm colors of the setting sun.

Home in Rangeley

The GETAWAY, Rangeley

Our GETAWAY-perfect place for relaxing and fun! It’s private but 1/2 mile to IGA and approx 1 mi to beautiful downtown Rangeley with great restaurants, bowling, arcade, darts and shuffleboard. Ltd access to snowmobile trails directly from the house. ATV is no longer allowed from our home. Trails can be accessed from IGA (park across the st., or Depot Rd (includes trailer parking) 3/4 mile from our home. Hiking and incredible scenery! Walking distance to Pickford Pub and mins o Mtn Star Estate.

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4.98 out of 5 average rating, 127 reviews

An open kitchen area showcases wooden cabinetry and modern stainless steel appliances. A spacious countertop is lined with cookware, while a cozy dining area with a large table can be seen at the far end. Natural light enters through multiple windows, enhancing the warm, inviting atmosphere.

Home in Stratton

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 cozy house for the outdoor enthusiast! The open floor plan & entertainment system are ideal for relaxing after a full day outside. Located near hiking & biking trails, 7 mi to Sugarloaf, 1.5 mi to Flagstaff Lake, 20 min to Rangeley. Outdoor dining area, grill, firepit, deck, & covered porch. The perfect spot to launch your adventures from! A guest favorite for many years!

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4.97 out of 5 average rating, 321 reviews

The open-concept living area showcases natural wood walls and a ceiling, with large windows allowing ample light. A soft sofa and a daybed are arranged around a round coffee table on a striped area rug. A staircase leads to the upper level, visible in the background.

Home in Farmington

Carriage House

Renovated circa 1920 carriage house in a quaint New England college town. Eight-minute walk to busy downtown with restaurants, bars, shops, and grocery store. Elegant contemporary style. Open concept downstairs with sofa, daybed (napping in the sun!), and chef-designed kitchen. Second level with two queen beds and small balcony. Adjoins miles of walking trails and forest, full of wildlife. Less than 5-minute drive to a 1.5 mile running trail along the Sandy River, with refreshing swimming.

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An open living space reveals a kitchen with a wooden island and white cabinetry, connected to a dining area featuring a wooden table and chairs. Steps lead to a cozy sitting area with a sectional sofa, surrounded by large windows allowing natural light.

5.0 out of 5 average rating, 125 reviews

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.

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4.88 out of 5 average rating, 8 reviews

Home in Kingfield

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.

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A serene scene features a person fishing by the river, surrounded by lush greenery and mountain views in the distance. The interior showcases wooden beams and a spacious kitchen with stainless steel appliances, complemented by bar stools along a large island.

5.0 out of 5 average rating, 96 reviews

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!

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A serene winter scene showcases a partially frozen lake at sunset, with vibrant hues of orange and purple reflecting in the sky. Pine branches frame the view, and distant mountains are faintly visible among a backdrop of evergreen trees.

4.88 out of 5 average rating, 42 reviews

Lakefront Cabin/Ski Mountains/Snowmobile/Fish/Hike

Cozy rustic cabin on a private road overlooking Flagstaff Lake, water access and mountain views and stunning sunsets. launch your kayak or canoe right from property. ITS 89 is at the beginning of the driveway, snowmobile from the property. Huge lawn with fire pit and plenty of firewood and outside seating. Plenty of parking. A short distance down the road is Myers Lodge. A popular beach spot. 15-20 minutes to Sugarloaf Mountain Ski resort and Bigelow Mountains/Hiking Trails

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4.85 out of 5 average rating, 13 reviews

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

LocationFamilyKitchen

5.0 out of 5 average rating, 19 reviews

Home in New Portland

Riverway Cottage

Welcome to Riverway! A cozy 2-bedroom cottage nestled beside the Carrabassett River. Just 30 min from Sugarloaf’s world-class skiing and snowboarding. Enjoy fly fishing, tubing, and swimming in the river or in the pool. Explore hiking, snowshoeing, snowmobile/ATV trails (no direct access from cottage). A short drive to Kingfield (15 minutes) and Farmington(1/2hr) shops & dining. We proudly offer 1-night stays-perfect for quick trips or last-minute overnights!

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A wooden dock extends into calm, reflective waters surrounded by a serene landscape. Potted flowers in vibrant colors add a touch of greenery, while the sky above features soft clouds and blue tones, enhancing the tranquil lakeside atmosphere.

4.99 out of 5 average rating, 67 reviews

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!

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