Holiday houses in Flagstaff Lake

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Top-rated holiday rentals in Flagstaff Lake

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

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Top Guest favourite
Cabin in Eustis
5 out of 5 average rating, 13 reviews

Perfect Getaway Cabin; Close to Sugarloaf

Relax with the whole family at this peaceful “barn” cabin close to everything you want in western Maine. Great proximity to both Sugarloaf and Rangeley and easy access to beautiful Flagstaff lake. ATV trails 1/2 mile away and you can snowmobile right from the cabin during the winter!Our beautiful cabin has everything you need to feel right at home and relax. 2 bedrooms, 1 bathroom, plus a bunk room means you have plenty of sleeping space for your whole crew to kick back and enjoy your getaway.

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Top Guest favourite
A cozy cabin exterior is framed by tall trees, featuring a welcoming sign on the front. Two chairs are positioned on the wooden porch, inviting guests to relax in nature. The gabled roof and wood paneling contribute to the cabin's rustic charm.
Guesthouse in Eustis
4.99 out of 5 average rating, 71 reviews

Tall Pines Cozy Cabin

PRICE INCLUDES ALL AIRBNB FEES! NO CLEANING FEE! You will find this peaceful cozy cabin nestled among tall beautiful red pine trees. Located in a quiet private community in Eustis. This space is perfect for a single person or a couple. The cozy cabin is located next to our home but is a separate stand-alone unit. A lot to offer in a small space. Outside there is a gas grill and a covered porch with chairs to enjoy in the warmer months. Sit and take in the peaceful surroundings or a good book.

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Top Guest favourite
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
4.95 out of 5 average rating, 170 reviews

Apres Ski Haus - Private Oasis

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!

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Top Guest favourite
A cozy cabin is shown warmly nestled among tall trees, featuring a covered front porch with steps leading up. The rustic exterior is complemented by a metal roof, and large windows provide ample natural light. An inviting outdoor area is visible, surrounded by nature.
Cabin in Coplin
5 out of 5 average rating, 45 reviews

Cozy Coplin Camp minutes to Sugarloaf

Welcome to your cozy camp in Coplin Plantation! Nestled in a serene, wooded setting minutes from Sugarloaf Resort, this retreat offers peaceful privacy and outdoor adventure. After a thrilling day on the slopes, warm up instantly beside the cozy gas fireplace. Enjoy easy access to world-class skiing, hiking, and snowmobile trails just minutes away. Features a full kitchen, comfortable beds, and scenic deck views. Perfect for families, couples, or friends looking for a classic Maine getaway!

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Top Guest favourite
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 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!

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Top Guest favourite
A cozy living area is highlighted by an electric fireplace set against a stone wall, providing a warm focal point. Two glasses of red wine sit on a rustic glass table, accompanied by decorative wood coasters and a small plant nearby.
Apartment in Kingfield
4.96 out of 5 average rating, 424 reviews

On The River 2 with Lucy the resident cat

On the River 2 is located in the heart of the historic downtown Kingfield on Main street with river views of the Carrabassett river. Miss Lucy Lu (Lucy) is the cat residents who lives in this special apartment. She is the host and will greet you. She loves people. She is an indoor kitty. There is a restaurant next door, the gallery is downstairs, swimming out the back of the building. Sugarloaf mountain close by. Mountains of possibilities to explore in the western area of Maine.

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Top Guest favourite
Apartment in Eustis
4.99 out of 5 average rating, 119 reviews

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!

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Top Guest favourite
The cabin's exterior showcases a rustic wooden facade surrounded by tall spruce trees. A spacious gravel area provides ample parking. The covered porch, adorned with seating, invites relaxation. A small storage shed is positioned to the right of the cabin.
Cabin in Rangeley
4.99 out of 5 average rating, 151 reviews

Evergreen Lodge-Rangeley Cabin, 3 bedroom & Loft

The perfect Home Base. Minutes to Saddleback, 1.5 mi to downtown with beach and boat ramp. Secluded in a very quiet, family freindly association neighborhood Direct ITS snowmobile access, NO ATV access. The home is very private, yet close to all Rangeley amenities. The Home boasts 3 bedrooms, two full bathrooms, fully equipped kitchen, memory foam mattresses throughout, Smart TV's in all bedrooms, hi speed wifi & plenty of parking for trucks & trailers. Any questions just ask.

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Guest favourite
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, 141 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.

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Guest favourite
Home in Eustis
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

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Top Guest favourite
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
4.97 out of 5 average rating, 126 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!

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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
4.99 out of 5 average rating, 68 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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Popular amenities for Flagstaff Lake holiday rentals