Vacation rentals in Flagstaff Lake

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Top-rated vacation rentals in Flagstaff Lake

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Top guest favorite

Cabin in New Portland

5 out of 5 average rating, 122 reviews

Cozy Cabin on the Carrabassett River

Enjoy four seasons of recreation while staying in a comfortable cabin overlooking the beautiful Carrabassett River. The cabin is nestled in 17 private acres but is close to services and restaurants, trails, and the iconic Wire Bridge. Snowmobile trails are accessible from the cabin, and ATV trails with parking are accessible from nearby Kingfield (6 miles north). Ski Sugarloaf, bike the Carrabassett Valley trails, hike the Bigelow Preserve, or just relax by the river - this area has it all!

Top guest favorite

Chalet in Kingfield

4.98 out of 5 average rating, 136 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

Apartment in Eustis

4.99 out of 5 average rating, 103 reviews

The Dead River Ranch-16 miles from Sugarloaf

A rustic, cozy lower level apartment that offers plenty of open space for a couples retreat. Enjoy, mornings of provided coffee and the great outdoors! 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, in Eustis village. Skiing or golfing at Sugarloaf Mountain is less then 25 minutes away. Come kick back in the great North Country!

Top guest favorite

Cabin in Rangeley

4.98 out of 5 average rating, 124 reviews

Evergreen Lodge-Rangeley Cabin, 3 bedroom & Loft

Relax in our cabin. Minutes to Saddleback, 1.5 mi to downtown with beach and boat ramp. Secluded in a very quiet, family freindly association neighborhood surrounded by spruce trees and wildlife. Direct ITS snowmobile access, NO ATV access. Spoil yourself in total comfort while exploring western Maine mountains. The home is very private, yet close to all Rangeley amenities. Fully stocked kitchen and everything you'll need for a great dinner. Any questions just ask. This is Rangeley !

Top guest favorite

Cabin in Kingfield

4.99 out of 5 average rating, 104 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

Home in Stratton

4.97 out of 5 average rating, 117 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. Close to hiking & biking trails, 7 mi to Sugarloaf Mountain, 1.5 mi to Flagstaff Lake boat launch, 20 min drive to Rangeley. Outdoor dining area, firepit , deck, & covered porch. It’s the perfect spot to launch your outdoor adventures from!

Guest favorite

Cabin in Coplin

4.87 out of 5 average rating, 143 reviews

Cozy Cabin close to Sugarloaf Mountain

This 1100 square foot cozy cabin in the woods is 8 miles north of Sugarloaf ski resort, 25 minutes north east of Rangeley Lake and 5 minutes from Flagstaff Lake. It is equipped with dimmable recessed lighting, a ceiling fan, a front porch, and back deck. There is a loft with a queen bed in addition to the queen bed in the bedroom. Wifi is available on sight as well as a 55" Roku smart TV. This cabin has had many recent updates primarily on the first floor and loft areas.

Guest favorite

Chalet in Carrabassett Valley

4.89 out of 5 average rating, 117 reviews

Welcome to our Shackteau! Close to loaf + trail!

Unique ski chalet five minutes from Sugarloaf access road, with snowshoe / XC ski trail from the property that connects to valley trail system. Cozy, all-wood interior with funky bunk bed tower, homey propane stove, and den with bar and large TV. Equally well-suited for families, friends, and responsible mountain enthusiasts! We love our shackteau and know you will, too! We received negative feedback on our last cleaner so we have a new AWESOME cleaner :)

Guest favorite

Cabin in Weld

4.94 out of 5 average rating, 117 reviews

Camp Bai Yuka/Little Camp (Log Cabin on Webb Lake)

Enjoy your stay on the banks of Webb Lake in our 2019 hand-crafted log cabin. This cabin is 35 ft from the high water mark and has views of the lake from all three bedrooms. This rental has access to a private beach ( 200 ft) and is in a secluded cove on the lake. For travelers unfamiliar with Weld, Maine, Weld is nested in the heart of the western mountains of Maine. Hiking Tumbledown and Mt Blue are only the beginning of the recreational opportunities.

Top guest favorite

Chalet in Sandy River

4.98 out of 5 average rating, 123 reviews

Mountainside at Saddleback - Sunsets! Views!

Welcome to the Last Chair Lodge - our family-friendly mountainside retreat at Saddleback Ski Area in Rangeley, ME. Incredible views - and sunsets - in all seasons. Ski-in/Ski-out in winter (natural snow dependent), in summer enjoy a peaceful, beautiful and comfortable mountain retreat. Come for outdoor adventures, time on the nearby lakes or just to unwind and soak in the scenery. Yes, we have A/C and fast fiber WiFi! HDTV w/streaming services included.

Guest favorite

Home in Carrabassett Valley

4.92 out of 5 average rating, 113 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

Cabin in Phillips

4.94 out of 5 average rating, 191 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.