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House vacation rentals in Flagstaff Lake

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Top-rated house rentals in Flagstaff Lake

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Top guest favorite
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
4.98 out of 5 average rating, 127 reviews

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.

Top guest favorite
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
4.98 out of 5 average rating, 127 reviews

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!

Top guest favorite
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.
Home in Eustis
5.0 out of 5 average rating, 124 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.

Top guest favorite
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
4.96 out of 5 average rating, 313 reviews

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.

Guest favorite
Home in Kingfield
4.86 out of 5 average rating, 7 reviews

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.

Top guest favorite
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.
Home in Eustis
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!

Guest favorite
Home in Eustis
4.92 out of 5 average rating, 48 reviews

Bigelow Alpine Lodge

This historic building was built in 1892 and has kept a lot of its original charm but now has been transformed into a gorgeous newly renovated 3 bedroom, 2.5 bath spacious home. The backyard overlooking the north branch of the Dead River leads you directly to Flagstaff Lake for ample outdoor recreation. Walking distance to our local grocery store, restaurants and shops. Spacious dining/living room, open kitchen with full amenities to make this the perfect getaway for your group!

Guest favorite
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.
Home in Eustis
4.88 out of 5 average rating, 41 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

Guest favorite
The exterior of a log cabin is showcased, featuring a large deck with wooden railings. A bank of large windows allows natural light inside, highlighting the cabin's open design. Stacks of firewood can be seen underneath the deck, ready for use.
Home in Phillips
4.95 out of 5 average rating, 96 reviews

Hurry Back.

Cozy log cabin located on a mountain side, with 60 acres access to hiking/snowshoe trails. Appalachian trail only minutes away. 16 miles south of Rangeley, home of Saddleback Mt. Relax, take it easy at this unique and tranquil getaway. Mountain views. Snuggle up to the wood stove or enjoy the outdoor fire pit. Relax in the hot tub under the stars. Winter guests will need a 4 wheel drive, vehicle to climb steep driveway. One of two Airbnb’s on property but plenty of privacy.

Guest favorite
Home in Eustis
4.82 out of 5 average rating, 11 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

Top guest favorite
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.
Home in Eustis
4.98 out of 5 average rating, 65 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!

Guest favorite
A serene riverbank is framed by lush green trees and foliage. Clear water reflects the surrounding nature, with smooth stones scattered along the shore. Gentle ripples indicate flowing water, creating a tranquil atmosphere for outdoor activities.
Home in Carrabassett Valley
4.92 out of 5 average rating, 132 reviews

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.

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