House holiday 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 favourite

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.

ValueLocationView

4.98 out of 5 average rating, 130 reviews

Top Guest favourite

A spacious farmhouse stands amidst a grassy area, illuminated by warm light from numerous windows. A covered porch extends along the front, featuring wooden chairs. The surrounding landscape includes mature trees providing a natural backdrop.

Home in Starks

Farm house, River, Island, animals & private Chef.

MARCH-APRIL DAILY. Medicine Hill is a 136 acre farm on the Sandy River complete with a swimming hole and an entire island to explore. We grow vegetables, herbs & flowers. Our animals include sheep, chickens & rabbits. You will have full access to all areas of the farm! Spend time fishing or relaxing on the river. Or literally just sitting on the porch unwinding and taking it all in. 4 private bedrooms have stunning views surrounded by trees or fields. And if the Chef is available..EAT!!!

LocationFamilyQuiet

4.94 out of 5 average rating, 171 reviews

Top Guest favourite

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

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.

LocationValueAir conditioning

5.0 out of 5 average rating, 127 reviews

Top Guest favourite

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 house for the outdoor enthusiast! The open floor plan & entertainment system are ideal for relaxing after a full day outside. Outdoor dining area, grill, firepit, deck, & covered porch. Close proximity to hiking, biking, swimming, & more! 7 miles to Sugarloaf, 1.5 miles to Flagstaff Lake. An amazing spot to launch your adventures from & a guest favorite for many years!

ValueFamilyGetting around

4.98 out of 5 average rating, 128 reviews

Top Guest favourite

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.

ValueLocationAccuracy

4.97 out of 5 average rating, 328 reviews

Top Guest favourite

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

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!

LocationFamilyAccuracy

5.0 out of 5 average rating, 100 reviews

Top Guest favourite

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

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.

LocationValueGetting around

4.95 out of 5 average rating, 102 reviews

Top Guest favourite

A charming exterior of The River House is depicted with its wooden siding and multiple windows. Colorful Adirondack chairs are arranged in the foreground, complemented by the spacious lawn. Tall trees surround the property, and a deck provides access to the inviting outdoor space.

Home in West Forks

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.

LocationFamilyAir conditioning

4.98 out of 5 average rating, 141 reviews

Top Guest favourite

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

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!

FamilyLocationCleanliness

4.99 out of 5 average rating, 70 reviews

Guest favourite

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 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.

LocationFamilyCleanliness

4.92 out of 5 average rating, 132 reviews

Superhost

The inviting living area features a stone fireplace with a mirror above it, surrounded by plants and wooden beams overhead. A wooden staircase leads to the upper level, while a dining area with several chairs is visible in the background, enhancing the warm and cozy ambiance.

Home in New Portland

The Riverfront Retreat - 27 minutes to Sugarloaf!

This vibrant farmhouse is surrounded by 800 ft. of Lemon Stream. Walk to the historic wire bridge! It is about 27 minutes to Sugarloaf and 8 minutes to Kingfield; located directly off Rt. 27 in route to Carrabassett Valley. You can hit the slopes then come home to a cozy, gas fireplace. There's a firepit by the stream to enjoy the stars in warmth. The home is full of color and organic decor. FAST STARLINK WIFI!

LocationFamilyAccuracy

4.85 out of 5 average rating, 180 reviews

Top Guest favourite

A charming two-story ski house is nestled in a snowy wooded area, featuring large skylights on the upper floor. A spacious deck extends from the front, while two parked vehicles are partially covered in snow. Trees with autumn leaves frame the home.

Home in Carrabassett Valley

Sugarloaf Home with amazing views

Sugarloaf Ski House, 10 minutes to baselodge, shuttle on call, awesome views, near crosscountry trails, restaurants, Outdoor Center. In summer months, 10 minutes to Sugarloaf Golf Course. Easy access to bike/ hiking trails, waterways, fishing. You can ski in and out from your vehicle from the ends of Lots E and F when the Bucksaw Quad is running. There's a ticket Kiosk at the base of the lift.

FamilyValueTV

4.96 out of 5 average rating, 108 reviews