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Vacation rentals in Flagstaff Lake

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Top-rated vacation rentals in Flagstaff Lake

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

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Top guest favorite
The A-Frame cabin is surrounded by tall trees and a snowy landscape, showcasing large windows that reflect warm light. A wraparound deck features outdoor seating, inviting relaxation in a serene wooded setting at dusk.
Cabin in Chesterville
4.99 out of 5 average rating, 168 reviews

Off-Grid Escape. Wood Fired Hot Tub, Snowshoes

Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- excellent swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

Top guest favorite
The exterior of the cabin is illuminated at dusk, highlighting the wooden structure and large windows. A hot tub is visible on the deck, surrounded by trees, inviting a serene and relaxing atmosphere. Warm light glows from inside, suggesting a cozy interior.
Cabin in Kingfield
4.96 out of 5 average rating, 136 reviews

Apres Ski Haus

This cabin is anything but ordinary! Nestled on an open bluff in the woods of Kingfield, Maine this architectural wonder is a perfect getaway for a couple or group. It's a warm and cozy space to come back and unwind after a long day of hitting the slopes or any four season activity. The open concept living room and newly remodeled kitchen have modern amenities like an espresso machine, Smart TV, and comfortable furnishings that will make you feel at home. Only 20 minutes to Sugarloaf Mountain!

Top guest favorite
A comfortable seating area is illuminated by natural light from a large window, offering a view of the water. A cozy throw is draped over the couch, and a decorative coffee table holds various magazines. A dog rests peacefully on the couch.
Cabin in Rangeley
4.98 out of 5 average rating, 107 reviews

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!

Top guest favorite
A cozy chalet is situated in a snowy landscape, framed by tall, bare trees. The wooden exterior combines rustic charm with modern design. A covered entrance welcomes guests, leading to a snow-covered pathway surrounded by a serene, wintry environment.
Chalet in Kingfield
4.98 out of 5 average rating, 152 reviews

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.

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 out of 5 average rating, 104 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
A tranquil outdoor space features a wooden pergola with seating and a grill, situated beside a hot tub. The fenced backyard is surrounded by tall trees, and the charming house is accentuated by a beautiful sunset sky.
Cabin in Kingfield
4.99 out of 5 average rating, 119 reviews

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.

Top guest favorite
Treehouse in Woodstock
4.98 out of 5 average rating, 277 reviews

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).

Guest favorite
The exterior of the house features a combination of dark metal and stone, complemented by large windows that provide views of the surrounding landscape. The entrance includes a wooden door, and a small stone pathway leads up to it, framed by fresh snow.
Tiny home in Le Granit Regional County Municipality
4.97 out of 5 average rating, 110 reviews

The Rifugio Rental Cottage Hot tub/mountain view

The rifugio is the perfect place to take refuge. A peaceful oasis surrounded by nature and mountains as far as the eye can see. The Rifugio offers you the freedom to make an authentic connection with nature and enjoy quality time alone or with others. As soon as you walk through the door, you are greeted in a warm and comfortable atmosphere. Large windows offer magnificent views of the surrounding mountains and in the distance we can see the tip of Lac Mégantic.

Guest favorite
A spacious living area features large windows that frame expansive mountain and water views. Comfortable seating includes a sectional sofa and chairs positioned for relaxation. A wooden coffee table sits in the center, adding a rustic touch to the cozy atmosphere.
Chalet in Rangeley
4.96 out of 5 average rating, 110 reviews

Rangeley Home with a View - Get Out of Dodge

Welcome to Out of Dodge in Rangeley Maine! A well Appointed Chalet with Panoramic mountain and water views. located just 15 minutes from Saddleback Ski Resort and only 5 minutes to Snowmobile and ATV trail access. Whether you’re coming for outdoor recreation or just to unwind and soak in the scenery, the view here is breathtaking in all seasons (especially fall!!) Family-friendly, High Speed Wi-Fi, 55" HDTV with surround sound and YouTube TV!

Top guest favorite
A tranquil view of a lake at sunset, showcasing vibrant hues of orange and pink reflecting off the water. Silhouetted trees line the horizon, providing a serene backdrop to the colorful sky.
Cabin in Eustis
4.99 out of 5 average rating, 102 reviews

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!

Top 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, 118 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.

Top guest favorite
The camp is nestled among tall trees, set slightly elevated above a clear stream. Large boulders and lush greenery surround the water's edge, offering a serene natural setting. The building features a wooden exterior with a sloped roof, harmonizing with the surrounding landscape.
Cabin in Phillips
4.94 out of 5 average rating, 200 reviews

Stream-side mountain retreat

This attractively renovated camp in the High Peaks region of western Maine is the perfect place to get away and unplug. Surrounded by conservation land, the camp is airy and bright, with views opening onto woods and stream, and is well screened. Solar panels provide water and electricity. There's limited satellite internet service for emailing and texting, and sometimes phone through wifi, depending on your service provider.

Popular amenities for Flagstaff Lake vacation rentals

  1. Airbnb
  2. United States
  3. Maine
  4. Flagstaff Lake