Holiday rentals in Sugarloaf Mountain

4.98 out of 5 average rating, 130 reviews

Chalet in Kingfield

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.

4.99 out of 5 average rating, 101 reviews

Flat in Eustis

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!

Train in Carrabassett Valley

4.94 out of 5 average rating, 173 reviews

Train Caboose on Mountain

Sugarloaf Village 1 - on mt ,w free shuttle. featured in "Maine Homes by Downeast" mag "Love Train". This beautifully restored caboose w/3 separate sleeping areas - a master bedroom w full bed - single comfortable bunk and a convertible couch. Fully equipped w many ammenities- Flat Screen tv w chromebox- tiled shower -great bedding/linens- full stove & microwave.-fridge- pots pans & cooking supplies -keurig & trad coffe pot-great deck & 1 1/4 yard w pines . U-Tube video JohannaFowler-x5w

Apartment in Carrabassett Valley

4.96 out of 5 average rating, 101 reviews

Ski In/Ski Out Sugarloaf Sugartree 2 Deluxe Studio

This cozy and comfy ski in/ski out condo is in a desirable location and just a short chairlift ride to the base of Sugarloaf Mountain. Ski or mountain bike directly from the condo! Family friendly. A queen bed settled in an alcove, queen murphy bed and pull out full size sofa bed provide plenty of sleeping space. Convenient indoor access to the pool, hot tubs, and sauna at the Sugarloaf Sports and Fitness Center (additional fees apply). Full kitchen, and one of the few with AC for summer!

4.96 out of 5 average rating, 362 reviews

Flat in Kingfield

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.

4.98 out of 5 average rating, 171 reviews

Cottage in Farmington

The cottage at Marble Farm.

This beautiful private cottage is the perfect place to unwind after a long day of adventure! New, bright and comfortable, this secluded cottage is conveniently located just 40 minutes from Sugarloaf, 50 minutes from Saddleback and 10 minutes to downtown Farmington. Feel free to walk, fat bike or x-country ski on nearly 4 miles of groomed private trails located just outside your front door! Contains a full kitchen for meal prep, as well as high speed internet, and climate control.

4.98 out of 5 average rating, 107 reviews

Flat in Kingfield

Village Top Floor With Riverview

Located right in downtown Kingfield, this cozy 1 bedroom, top floor unit provides a comfortable escape as well as easy access to in-town amenities. The perfect getaway spot for a couple or a single traveler. Right in the heart of the Western Maine mountains: 20 minutes from Sugarloaf, minutes from the snowmobile and mountain biking trailheads, kayaking, fishing, etc. If you're into outdoor activity this is the place to be! Easy walk to local restaurants and shops.

Chalet in Carrabassett Valley

4.88 out of 5 average rating, 113 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 :)

4.92 out of 5 average rating, 112 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.

4.93 out of 5 average rating, 186 reviews

Cabin in Phillips

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.

Cabin in Carrabassett Valley

4.92 out of 5 average rating, 254 reviews

Private Cabin next to Narrow Gauge Trails & River

Historic Ski camp built in 1957! Located a mile from Sugarloaf access road. View of Sugarloaf! Private trail to the Narrow Gauge Parking lot & Trail system. Biking and Hiking right out the door! Only a 4 minute drive to Super Quad and on the Shuttle route. Located within a mile from Anti~Gravity Center, Outdoor Center, Hugs restaurant, Carrabassett Public Library, Mountain Side Grocery Store & Gas station.

Holiday home in Carrabassett Valley

4.88 out of 5 average rating, 109 reviews

The Loaf View - 3 Bed Apt - 10 min from Sugarloaf

Relax, ski, snowshoe, mountain bike, hike or just flake out in our spacious three-bedroom lower-level apartment in Reddington East -- just 10-minutes from the Loaf. 1500 square feet, fully equipped kitchen, comfortable living area great for watching the game, blazing fast internet, and a spectacular view of the mountain. There's plenty of room for your skis, coats, and other items in the secure entryway.

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Popular amenities for Sugarloaf Mountain holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Sugarloaf Mountain

4.91 out of 5 average rating, 57 reviews

Cabin in Coplin

Pip's Place-10 Min to Sugarloaf/5 min to Flagstaff

LauraRating, 5 stars4 weeks ago

Cute cabin near Sugarloaf mountain. The cabin has a warm woodsy smell, which added to the charm. Nice living room area with a sofa and everything you need in the kitchen to prep meals. Bedrooms aren't fancy but the beds are comfortable and they accommodated us nicely. We loved the Looney Moose restaurant down the road and the proximity to Sugarloaf and nice hikes. Laura was very responsive and even accommodated a later check-out since I was running the Sugarloaf marathon and wanted to shower after. Would stay again!

5 out of 5 average rating, 34 reviews

Fun all season home on West Mountain.

KathyRating, 5 stars2 months ago

The place was perfect! Kelly was a great host complete with alerting us to look out the window to see the northern lights! No complaints about her large comfortable home.

Apartment in Carrabassett Valley

5 out of 5 average rating, 18 reviews

Valley Crossing 2 bedroom condo

RandyRating, 5 stars4 months ago

We were very happy with Pam's place. it is clean and comfortable and has a cool eclectic vibe. Excellent equipped kitchen, lots of towels in the bathroom. The Hill is very accessible from Pam's place, only a 10 minute drive away. Nice pub with craft beer down the hallway, a nice surprise. Great value for us Canucks, we will be back!

Townhouse in Carrabassett Valley

4.98 out of 5 average rating, 53 reviews

Spacious Family Condo on Sugarloaf Mountain Resort

BrendonRating, 5 stars4 months ago

Phil’s place feels like your friends invited you to visit. Comfortable and functional but not feeling like it was minimized or staged. The quality of the property and location stood out as well but Phil made it feel like our home for the weekend! Views from every window and warm and comfortable for eight of us and still offered privacy with the 3 and 1/2 baths! Book it if you can! Plus it’s Sugarloaf!

5 out of 5 average rating, 22 reviews

Ski In to this dog friendly West Mountain Home!

CharlotteRating, 5 stars1 month ago

This house was excellent- so much space for our group of friends and dogs too. Our hosts were also really friendly and responsive- they brought us up a crock pot when we needed one, which was just a nice thing to do. Would definitely come back and stay again.

Superhost

5 out of 5 average rating, 4 reviews

Stunning 5 BR Home Ready For Your Summer Visit AC!

IanRating, 5 stars9 months ago

Came up to play the golf course and the house was in a great location to get to and from the course quickly. House was great for a group with plenty of room.

Apartment in Carrabassett Valley

4.96 out of 5 average rating, 70 reviews

Ski-in-ski-out-sugarloaf-condo

ChristopherRating, 5 stars1 month ago

Shawn’s place was perfect for our family of 4 and our dog. Directly across the street from the Health and Fitness Center and 60 seconds to the base. Had a great trip for some Spring skiing. Great location and value for the price we paid. Thank you.